Search Eastern Maryland Cottage Rentals from CA $144

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Eastern Maryland Cottages

Shore Point Cottages
Fridge, microwave, stovetop, dishwasher

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (200)
"We had an amazing time we even extended our stay . The management I believe her name was Erin was absolutely amazing , she was friendly and helpful . The property was so clean and so convienent. We will be back great place to stay ."
The price is CA $152
CA $216 total
includes taxes & fees
Dec 24 - Dec 25
Shore Point Cottages
Comfortable cottage in gated community, 5 mins to OC and Assateague
Property grounds

Comfortable cottage in gated community, 5 mins to OC and Assateague

9.8 out of 10, Exceptional, (26)
"Very nice, clean and quiet location. Would definitely book again."
The price is CA $144
CA $454 total
includes taxes & fees
Jan 20 - Jan 21, 2025
Comfortable cottage in gated community, 5 mins to OC and Assateague
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Interior

Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG

10.0 out of 10, Exceptional, (22)
"This is the cutest little beach cottage, steps to the beach! The owner is very responsive and super hospitable. We will be staying again! "
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Exterior

Private Carriage House Retreat on a 33 Acre Historic Working Estate

10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (135)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
Property grounds

Your Own Stonegate Cottage— North OC—4 blocks to the Beach

10.0 out of 10, Exceptional, (16)
"We love this location and the hosts"
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (116)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Terrace/patio

Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower

8.4 out of 10, Very good, (48)
"The house was nice. Neighbor quiet. It was nice there is a small park across the street for the dog. Had everything I need in the house. It was nice I did not have to bring my own sheets and towels. They were supplied to us. The beach is a short drive up the street, maybe a minute or two and there was plenty of parking. I would stay here again if I go down to ocean city again."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Cozy Coastal Cottage Ocean Pines
Fridge, microwave, oven, stovetop

Cozy Coastal Cottage Ocean Pines

9.2 out of 10, Wonderful, (20)
"Property was just as shown and couldnt have asked for better communication."
Cozy Coastal Cottage Ocean Pines
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (170)
"The Carpenter Street Cottage is a great place to stay. Very clean and comfortable and has all of the necessary amenities. The location is perfect for walking throughout the town. I will definitely stay there again! "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
Fridge, microwave, oven, stovetop

Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI

8.4 out of 10, Very good, (11)
"Was a great place for our family vacation. Even though it was right off of Coastal Highway the noise from the road was not too bad especially with the AC units running. Very close to the beach & perfect for walking our dog. The cottage is bigger inside than it looks. Didn't particularly care for the shared laundry but, we made it work - only had to do one load anyway. Looking for some privacy away from condo life, we recommend this little cottage."
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
Waterfront, cozy cottage with private pool on 27 acres
Beach nearby

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres
New to VRBO! Cozy cottage close to everything!
Fridge, microwave, oven, stovetop

New to VRBO! Cozy cottage close to everything!

10.0 out of 10, Exceptional, (1)
"We had a great trip. The house was in the perfect location. Close to shopping, restaurants, and the beach made for the perfect vacation."
New to VRBO! Cozy cottage close to everything!
A pair of bay view cottages with cable & free WiFi - walk 2 blocks to the beach

A pair of bay view cottages with cable & free WiFi - walk 2 blocks to the beach

7.6 out of 10, Good, (9)
"This Stay was very disappointing. From the check-in process, where the property management company made you come in person to get a blank envelope since the door had a keycode, to the ants throughout the kitchen and bathroom there were some minor annoyances but there were also some major issues. 1) in unit B one of the bedrooms did not have heat. If it was summer this may not be an issue but when it is getting down into the 30s at night that means its not a usable room. 2) The bunk beds...
A pair of bay view cottages with cable & free WiFi - walk 2 blocks to the beach
Chesapeake Romantic Waterfront Home with Private Pool
Interior

Chesapeake Romantic Waterfront Home with Private Pool

8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront property with private boat ramp and new dock!
Outdoor dining

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
Charming Salisbury Getaway w/ Grill & Fire Pit!
House (3 Bedrooms) | Interior

Charming Salisbury Getaway w/ Grill & Fire Pit!

3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!
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.
Don't see what you're looking for?
See all available properties in Eastern Maryland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Eastern Maryland

Majestic Hotel & Apartments
Basic Apartment, 2 Bedrooms, Non Smoking | Private kitchen

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments
Shore Point Cottages
Fridge, microwave, stovetop, dishwasher

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (200)
"We had an amazing time we even extended our stay . The management I believe her name was Erin was absolutely amazing , she was friendly and helpful . The property was so clean and so convienent. We will be back great place to stay ."
The price is CA $152
CA $216 total
includes taxes & fees
Dec 24 - Dec 25
Shore Point Cottages
Coconut Malorie Resort Ocean City a Ramada by Wyndham
Studio, 1 King Bed, Non Smoking | Balcony

Coconut Malorie Resort Ocean City a Ramada by Wyndham

3.0 star property
7.4 out of 10, Good, (1236)
"Nice to have a kitchen and separate bedroom "
Coconut Malorie Resort Ocean City a Ramada by Wyndham
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.

Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between CA $144 and CA $152 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Eastern Maryland?
There are multiple cottages in Eastern Maryland with a total average guest review rating of 9.3, so you’re sure to snag the ideal place. Planning a trip to Ocean City? Frontier Town Campground is one property recommended by travelers. This 2-star cottage includes amenities like a swimming pool and a barbecue grill. 103 79th Street 3 Bedroom Cottage By Redawning is another popular escape where you’ll be close to nature. WiFi and a patio are just a couple of the conveniences you can expect at this 3-star pick in Ocean City.
How many cottages are there in Eastern Maryland?
Explore our 28 cottages in Eastern Maryland and reserve your favorite. Whether you’re dreaming of a vacation with the whole fam or a break with pals, your perfect stay is clicks away with Expedia.
Are there any family-friendly cottages in Eastern Maryland?
You’ll find family-friendly cottages in locations across Eastern Maryland, including Ocean City. Frontier Town Campground is one property that’ll meet your needs in this bustling city. It has a 2-star rating and conveniences like a playground and a barbecue grill. Also consider 103 79th Street 3 Bedroom Cottage By Redawning. With WiFi and clothes washing facilities, this 3-star cottage in Ocean City will make you and your companions feel at home. Once you’ve unpacked your suitcase and settled in, get out and explore Ocean City. Look forward to memorable moments together at family-friendly attractions such as Ocean City Beach and Maryland Beach.
Why book your cottage in Eastern Maryland with Expedia?
We think that vacations should be easy, so if you’re seeking cottages in Eastern Maryland at an affordable price, Expedia delivers. Save those pennies and go for a cheap option surrounded by wilderness, or splurge on a luxury cottage to pamper your loved ones.
How can I find cheap cottages in Eastern Maryland?
Expedia can help you look for cheap cottages in Eastern Maryland. To find your special stay in just a few keystrokes, try out our handy filter tool to refine your search by budget, star rating and amenities.
What is there to do in Eastern Maryland near my cottage?
Whether you like shopping, sightseeing, relaxation or adventure, Eastern Maryland has something to suit all tastes! The terrific city of Ocean City boasts plenty of things to see and do, including Ocean City Beach, Seacrets Distilling Company and Trimper’s Rides. If you’re on your way to Berlin, Globe Theater, Main Street Berlin and Calvin B. Taylor House Museum will fill up your itinerary.