A marina with numerous boats docked at wooden piers under a clear sky.

Search Eastern Shore Cottages

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Eastern Shore cottages

A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (404 reviews)
"Everything was clean and comfortable. Would stay here again."
United States
Kelly
$82 nightly
The price is $92
Dec 1 - Dec 2
Total with taxes and fees
Shore Point Cottages
Front of property

2. 6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
$242 nightly
The price is $271
Nov 18 - Nov 19
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
A wooden cabin with a white door, a wreath, a caution sign, a welcome mat, potted plants, and outdoor seating.

3. Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!

Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
Seaford
10.0 out of 10, Exceptional, (1 review)
"This was a clean, comfortable place to stay. We only stayed one night, but would've enjoyed staying longer. Sitting outside with coffee in the morning was special. The number of different birds we heard was amazing. We didn't have time to explore the pond, but it added to a nice, quiet stay."
United States
Whitney H.
$137 nightly
The price is $152
Nov 22 - Nov 23
Total with taxes and fees
Cozy County Autumn Escape at the Millpond Cottage - Pet Friendly!
A single-story mobile home with a front porch and steps leading to the entrance.

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

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (58 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
$301 nightly
The price is $337
Nov 15 - Nov 16
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
A single-story house with a front porch, a staircase leading to the entrance, and a small deck.

5. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$225 nightly
The price is $238
Nov 10 - Nov 11
Total with taxes and fees
Deal Island Bay Cottage
A wooden deck with a hot tub, lounge chairs, and a view of the water.

6. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$398 nightly
The price is $416
Nov 17 - Nov 18
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

7. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (60 reviews)
"Unique charming place to relax."
United States
Nimia N.
$205 nightly
The price is $217
Nov 10 - Nov 11
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A residential area with houses, a parking lot, and a body of water in the background.

8. Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (18 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$200 nightly
The price is $212
Nov 28 - Nov 29
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A wooden deck with a white railing overlooking a calm body of water and a distant bridge.

9. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
$713 nightly
The price is $799
Nov 12 - Nov 13
Total with taxes and fees
Game Room! Waterfront Group Haven in Ocean Pines
A waterfront house with a balcony, dock, and a view of the water.

10. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (674 reviews)
"First time here and we absolutely loved it."
United States
Melissa
$127 nightly
The price is $143
Dec 10 - Dec 11
Total with taxes and fees
Key West Cottages
A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

11. EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Georgetown
9.8 out of 10, Exceptional, (63 reviews)
"Great stay. We enjoyed the pool and property."
United States
Holly S.
$201 nightly
The price is $205
Nov 10 - Nov 11
Total with taxes and fees
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

12. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$233 nightly
The price is $258
Nov 10 - Nov 11
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

13. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
$270 nightly
The price is $286
Nov 10 - Nov 11
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
A single-story house with a covered porch, a number '374' on the side, and a covered grill area.

14. Charming 1-bedroom cottage with loft in Rehoboth Beach

Charming 1-bedroom cottage with loft in Rehoboth Beach
Truitts Park
9.8 out of 10, Exceptional, (26 reviews)
"loved our stay!"
United States
Clair H.
$315 nightly
The price is $322
Nov 10 - Nov 11
Total with taxes and fees
Charming 1-bedroom cottage with loft in Rehoboth Beach
14

15. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
$470 nightly
The price is $521
Nov 10 - Nov 11
Total with taxes and fees
Plum Point Cottage #14
Fire pit (2)

16. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
$495 nightly
The price is $548
Nov 10 - Nov 11
Total with taxes and fees
Plum Point Cottage #15
A wooden deck with wicker furniture, a round table, and a fire pit.

17. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
$539 nightly
The price is $614
Nov 10 - Nov 11
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Welcome to Creekside Retreat!

18. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (141 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
$310 nightly
The price is $336
Nov 10 - Nov 11
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
A wooden deck leading to a house surrounded by dense trees.

19. Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (92 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
$298 nightly
The price is $330
Nov 15 - Nov 16
Total with taxes and fees
Cozy Spring House in Gorgeous Chadds Ford!
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore Hotel Reviews

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"I enjoyed my time here a lot. The staff were kind and helpful. They had a lot of stuff in the hotel I didn’t know about, like a bar, restaurants, arcades, and a gym. The room was very clean. The only minor nitpick I had is I wish the showers had a bar of soap. There’s one in the bathroom sink, but it’s too small to shower with. Other than that, it was perfect and I can’t wait to come back again."
Alex 2-night trip
Posted 1 hour ago
Grand Hotel Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,690
Accommodation
36 Cottages
Lowest Price
$92
Highest Price
$799

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between $92 and $799 per night for cottages in Eastern Shore. No matter your budget, a fantastic stay is just clicks away on Expedia. 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?
Eastern Shore offers multiple cottages with a total average guest review rating of 9.7. Planning a trip to Ocean City? Travelers prefer Frontier Town Campground, a 2-star property with a swimming pool and a barbecue grill. Another top pick where you can escape the hustle and bustle is 103 79th Street 3 Bedroom Cottage By Redawning. It has a 3-star rating and amenities such as a nearby beach and a patio.
How many cottages are there in Eastern Shore?
Take your pick of 36 cottages in Eastern Shore. Whether you're traveling with the whole family, as a couple or with a group of workmates, Expedia will help you find the perfect space.
Are there any family-friendly cottages in Eastern Shore?
There sure are. Whether it's in one of Eastern Shore's bustling cities or way out in the wilderness, the unique charm of a cottage is ideal for family fun. If Ocean City is your destination, book a stay at Frontier Town Campground. This 2-star option features a playground and clothes washing facilities. Another great 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. After you've unpacked your luggage, it's time to discover the best of Ocean City. Look forward to memorable moments together at family-friendly attractions like Ocean City Beach and Jolly Roger Amusement Park.
Why book your cottage in Eastern Shore with Expedia?
Booking a cottage in Eastern Shore is as easy as deciding on your travel dates and picking your ideal place for a getaway in the outdoors. From luxurious retreats to budget-friendly stays and cottages that feature amenities like a kitchenette, Expedia has something for all traveler tastes. As for unbeatable deals? We've have them as well!
How can I find cheap cottages in Eastern Shore?
The quickest way to score cheap cottages in Eastern Shore is with Expedia's filter tool. Narrow your search by budget, star rating and amenities to snag awesome rates in a couple of clicks.
What is there to do in Eastern Shore near my cottage?
The best accessory to take on your Eastern Shore vacation is a good itinerary! Jolly Roger at the Pier, Inlet Park and Ember's Island Miniature Golf are some of the most popular sights if you're heading to Ocean City. Salisbury also has plenty of superb attractions, such as Poplar Hill Mansion. Want to explore more? Visit Pemberton Historical Park and Ward Museum of Wildfowl Art too.

Explore a world of travel with Expedia