Search Eastern Shore Cottage Rentals from CA $144

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Browse Select Eastern Shore 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 $156
CA $220 total
includes taxes & fees
Dec 30 - Dec 31
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
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My wife and I, and our daughter's family (including our grandkids (ages 5 and 8) spent an amazing long weekend at Spring Cove Farm. We all loved our stay so much. The house was spotlessly clean and had everything we needed and the pier/water was gorgeous with ample kayaks and paddle boards. The kids fished from the pier for hours upon hours each day, and were thrilled at the selection of toys. Our daughter and son-in-law were working remotely and the Wi-Fi and Internet worked perfectlu. Dr....
Secluded Waterfront Cottage on 200 acre farm near Queenstown
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
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
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (14)
"The house is great, so clean and well-equipped and has everything you need for a comfortable stay. Kim delivered delicious crabs right to the dinner table! We enjoyed riding the bikes around the island. Smith Island Bakery is only a few doors down!"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
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!
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.
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Other property types in Eastern Shore

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 $156
CA $220 total
includes taxes & fees
Dec 30 - Dec 31
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)
"A bit dated but still in good shape and decent value, big room. Water came in under the counter during heavy rain. Nevertheless, I'd stay again."
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 Shore cost?
Prices for cottages in Eastern Shore range between CA $144 and CA $156 per night. No matter your budget, you’ll find the perfect place to soak up nature’s beauty. 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 Shore?
There are multiple cottages in Eastern Shore with a total average guest review rating of 9.4, so you’re sure to find a place that suits your tastes. Planning to stay in Ocean City? Frontier Town Campground is one property recommended by guests. This 2-star cottage includes amenities like a barbecue grill and a swimming pool. 103 79th Street 3 Bedroom Cottage By Redawning is another highly rated getaway where you can unwind close to nature. Clothes washing facilities and a patio are just two of the conveniences waiting for you at this 3-star option in Ocean City.
How many cottages are there in Eastern Shore?
Eastern Shore has 32 cottages to choose from. Enter your dates and destination and plan your next escape today.
Are there any family-friendly cottages in Eastern Shore?
Yes there are. Whether it’s in one of Eastern Shore’s buzzing cities or way out in the wilderness, the rustic charm of a cottage is perfect for traveling families. If Ocean City is your chosen destination, stay at Frontier Town Campground. This 2-star option comes with a playground and WiFi. Another superb choice is 103 79th Street 3 Bedroom Cottage By Redawning. Also in Ocean City, this family-friendly cottage has a 3-star rating and includes clothes washing facilities and WiFi. Once you’ve unpacked your luggage, start sightseeing around Ocean City. Enjoy memorable days out at family-friendly attractions such as Ocean City Beach and Maryland Beach.
Why book your cottage in Eastern Shore with Expedia?
We think that traveling should be a piece of cake, so if you’re on the lookout for cottages in Eastern Shore at a nice price, Expedia delivers. Stick to the budget and opt for a low-cost option far from the rush of the city, or book a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Eastern Shore?
Expedia is here to help you easily track down cheap cottages in Eastern Shore. To lock in your dream stay in a few quick keystrokes, try out our convenient filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Eastern Shore near my cottage?
No matter your interests, there are countless things to keep you busy in Eastern Shore. If you’re heading to Ocean City, check out Ocean City Beach, Seacrets Distilling Company and Trimper’s Rides. Planning a getaway in Berlin? Globe Theater, Main Street Berlin and Calvin B. Taylor House Museum are among the top sights in this city.