Title: Chester Vacation Rentals from CA $219: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000440455.Destination-Travel-Guides)

![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is  at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Patricia Knorr

# Chester Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-13&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-14&endDate=2025-12-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/de679fa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/b08b990c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/efcaae35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/6e19a811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Adorable two-bedroom retreat close to Easton, Denton, Centreville

[](https://www.expedia.ca/Adorable-Two-Bedroom-Retreat-Close-To-Easton.h87799498.Hotel-Information)

Queen Anne

10/10

Exceptional

(26)

"Quiet, quaint....perfect"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Catherine M.

CA $260

CA $493 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Adorable-Two-Bedroom-Retreat-Close-To-Easton.h87799498.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### First Floor Studio Apartment in Historic Chestertown

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

Chestertown

9.6/10

Exceptional

(108)

"Amazing and neat and very private "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander M.

CA $136

CA $219 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/9eb7ac3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/259066d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/25541a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HGTV quality, private guest suite, country getaway with hot tub & fire pit

[](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information)

Centreville

10/10

Exceptional

(8)

"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Renee P.

CA $271

CA $605 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/89a58d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/aea8e7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/da0262a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Coastal/Country Home w/3 Acres & Sauna!

[](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

Stevensville

9.6/10

Exceptional

(32)

"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pamela

CA $112

CA $362 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/99582f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax on Kent Island in a 4 Bedroom Home w/Waterview!

[](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

Stevensville

9.8/10

Exceptional

(42)

"We had a great stay! The property has everything we needed and host was easy to communicate with "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie S.

CA $67

CA $303 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. 

[](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

Grasonville

9.6/10

Exceptional

(12)

"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe C.

CA $344

CA $575 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/0e96ebfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/07d26e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/9130ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Walk to Beach! King Bed & Free Beach Passes

[](https://www.expedia.ca/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

North Beach

10/10

Exceptional

(17)

"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer B.

CA $112

CA $435 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/a768e65e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/f86ddc27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/4940f0a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118830000/118824200/118824130/38d6910b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Upscale Condo in Annapolis

[](https://www.expedia.ca/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.Hotel-Information)

Historic District

10/10

Exceptional

(1)

"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer H.

CA $394

CA $831 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Annapolis-Hotels-Upscale-Condo-In-Annapolis.h118824130.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/952fef86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/a1db5475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/13d9abf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/122000000/121090000/121084800/121084764/688e056a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chesapeake Bay Harbor View in a central location to events/restaurants

[](https://www.expedia.ca/Rock-Hall-Hotels-Chesapeake-Bay-Harbor-View-In-A-Central-Location-To-Eventsrestaurants.h121084764.Hotel-Information)

Rock Hall

10/10

Exceptional

(2)

"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Todd W.

CA $310

CA $375 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Rock-Hall-Hotels-Chesapeake-Bay-Harbor-View-In-A-Central-Location-To-Eventsrestaurants.h121084764.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/w1179h1552x0y10-4ae4c675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/a52717e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/d32606e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/6b784e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

[](https://www.expedia.ca/North-Beach-Hotels-Charming-2-Bedroom-1-Bath-Cottage-With-AC.h114309947.Hotel-Information)

North Beach

9.6/10

Exceptional

(4)

"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jana S.

CA $176

CA $380 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/North-Beach-Hotels-Charming-2-Bedroom-1-Bath-Cottage-With-AC.h114309947.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/cd8d2b75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/2b0352ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/w4000h1729x0y0-ae4201db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92080200/92080111/68ce83bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BAYSIDE BUNGALOW

[](https://www.expedia.ca/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information)

Rock Hall

10/10

Exceptional

(52)

"Very quaint and quiet place to stay. Very relaxing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roger

CA $275

CA $416 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Rock-Hall-Hotels-BAYSIDE-BUNGALOW.h92080111.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/cc3df3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/f9a89b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Pet-Friendly Stay - Near Bay & Beaches.

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information)

Annapolis

10/10

Exceptional

(6)

"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristina

CA $323

CA $775 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/f520f52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0e2deec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0fab08c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront Oasis of Annapolis Star

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

Annapolis

10/10

Exceptional

(81)

"Owners were great hosts. Loved this property!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas

CA $285

CA $570 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/674bc712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/14020520.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/9c7dbc30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99520000/99518900/99518844/10010e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views

[](https://www.expedia.ca/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

Arnold

10/10

Exceptional

(6)

"Enjoyed the stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kedra B.

CA $181

CA $501 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Arnold-Hotels-Bung-A-Flo-Tiny-Bohemian-Designed-Floating-Home-W-360-Waterfront-Views.h99518844.Hotel-Information)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/aaa820d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/67700a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d4e67bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

[](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information)

North Beach

10/10

Exceptional

(31)

"Perfect place to spend quality time with our three adult children and their significant others. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Malarkey F.

CA $132

CA $554 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/dc0187f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/b40196ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/bb91d7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/3f9288e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Neptune by the Water - Pet Friendly Fenced Yard

[](https://www.expedia.ca/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information)

Cape Saint Claire

9.8/10

Exceptional

(11)

"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa S.

CA $238

CA $729 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Annapolis-Hotels-Neptune-By-The-Water.h101897342.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/5eca3b46_edited_e784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/10e31f36_edited_f301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/681a375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

[](https://www.expedia.ca/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

Shady Side

10/10

Exceptional

(4)

"Would stay here again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas D.

CA $198

CA $587 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/77000000/76340000/76334800/76334762/dafdf58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76340000/76334800/76334762/d96cb9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76340000/76334800/76334762/8658cc56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76340000/76334800/76334762/4c7a5764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New! Stylish downtown home w/awesome outdoor area!

[](https://www.expedia.ca/Stevensville-Hotels-New-Stylish-Downtown-Home-Wawesome-Outdoor-Area.h76334762.Hotel-Information)

Stevensville

9.8/10

Exceptional

(26)

"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marjorie N.

CA $304

CA $693 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Stevensville-Hotels-New-Stylish-Downtown-Home-Wawesome-Outdoor-Area.h76334762.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/d512df51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/66cb9c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/e9152c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/119000000/118720000/118717300/118717298/852031b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

[](https://www.expedia.ca/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

Pasadena

CA $217

CA $582 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Pasadena-Hotels-FLOHOM-14-Luxury-Houseboat-With-Chesapeake-Bay-Panoramic-Views.h118717298.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/06a8a8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/e5c30638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/3a482076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89060000/89057700/89057630/762da084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large 2 bedroom house with private parking in a nice neighborhood

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Arnold

9.4/10

Exceptional

(36)

"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jim G.

CA $180

CA $447 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Arnold-Hotels-Large-2-Bedroom-House-Private-Parking-Nice-Neighborhood.h89057630.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&regionId=3000440455&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Maryland%2C+United+States+of+America&regionId=3000440455&latLong=38.975391%2C-76.289398&adults=2&startDate=2026-03-13&d1=2026-03-13&endDate=2026-03-16&d2=2026-03-16&lodging=CONDO)

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## Top Chester Hotel Reviews

![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg)

### Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Courteous and helpful staff. Very clean. "

[](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg)

### Historic Inns of Annapolis

10/10 Excellent

"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."

[](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Candlewood Suites Annapolis by IHG](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f27fb62d_y.jpg)

### Candlewood Suites Annapolis by IHG

10/10 Excellent

"Our room was super clean! The staff was great!"

[](https://expedia.ca/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information)

![Courtyard by Marriott Annapolis](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg)

### Courtyard by Marriott Annapolis

10/10 Excellent

"Clean. Friendly. Balcony. Value"

[](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information)

![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg)

### DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Clean upscale rooom..bed was amazing "

[](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg)

### Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Fantastic hotel and they upgraded us to a room with a stunning view!"

[](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information)

![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg)

### Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."

[](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg)

### The Westin Annapolis

10/10 Excellent

"Spectacular "

[](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg)

### Crowne Plaza Annapolis by IHG

10/10 Excellent

"Excellent from check in to check out, highly recommend!"

[](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals)

- [Vacation Homes in Chester ](https://expedia.ca/Chester-Private-Vacation-Homes.d3000440455-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Chester ](https://expedia.ca/Chester-Cottages.d3000440455-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Chester ](https://expedia.ca/Chester-Apartments.d3000440455-aaApartments.Travel-Guide-Accommodation)
- [B&B in Chester ](https://expedia.ca/Chester-Bed-And-Breakfast.d3000440455-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Houseboats in Chester ](https://expedia.ca/Chester-Houseboats.d3000440455-aaHouseboats.Travel-Guide-Accommodation)
- [Condo Rentals in Chester ](https://expedia.ca/Chester-Condos.d3000440455-aaCondos.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.ca/Chester-Motels.d3000440455-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.ca/Chester-Guest-Houses.d3000440455-aaGuestHouses.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.ca/Chester-Inns.d3000440455-aaInns.Travel-Guide-Accommodation)
- [Farmstay in Chester ](https://expedia.ca/Chester-Agritourism.d3000440455-aaAgritourism.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.ca/Chester-Villas.d3000440455-aaVillas.Travel-Guide-Accommodation)
- [Cabin Rentals in Chester ](https://expedia.ca/Chester-Cabins.d3000440455-aaCabins.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Chester?

### What are some of the best vacation rentals that Chester has to offer?

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