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

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Eastern Shore cottages

A row of blue mobile homes with white railings and a covered porch area, located on a street with a 'One Way' sign visible.

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (374 reviews)
"Good and cute environment"
United States
junghyun
$95 nightly
The price is $107
Sep 13 - Sep 14
Total with taxes and fees
Shore Point Cottages
A wooden cabin with a front porch, a door with a wreath, and a window.

2. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
$140 nightly
The price is $148
Sep 10 - Sep 11
Total with taxes and fees
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
A two-story house with a covered porch, wooden posts, and a red and white trim.

3. Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
$231 nightly
The price is $257
Sep 18 - Sep 19
Total with taxes and fees
Pet-friendly Smith Island Cottage w/ Golf Cart!
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

4. 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, (52 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
$199 nightly
The price is $210
Sep 10 - Sep 11
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A single-story mobile home with a front porch and steps leading to the entrance.

5. 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, (54 reviews)
"Convenient amenities at Assateague Point, easy access to Assateague Island and OCMD. Everything in the unit was clean, in proper working order, and we had everything we needed for our family with young children. Would definitely stay here again."
United States
Alexandra
$323 nightly
The price is $362
Sep 22 - Sep 23
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
A two-story house with a covered porch, wooden posts, and a red and white trim.

6. Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell
10.0 out of 10, Exceptional, (23 reviews)
"My husband and I visited Smith Island for the first time for a two night stay. The house is clean and adorable and the owner goes out of her way to ensure you have a wonderful stay. A golf cart is all charged up for you to enjoy trips around the island. Bicycles are provided for you to ride too. Coffee Keurig cups, filtered water in the frig, and even bug spray are provided in case you forgot to bring yours. From arriving on the ferry to our trip back to Crisfield we encountered friendly people....
United States
Heather
$210 nightly
The price is $232
Sep 13 - Sep 14
Total with taxes and fees
Pet-Friendly Smith Island Cottage w/ Golf Cart!
A single-story house with a front porch, a staircase leading to the entrance, and a small deck.

7. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 reviews)
"We were there for our granddaughter's wrestling tournament in Salisbury. House was excellent, quiet and clean. Beautiful home. Thank you."
United States
Christopher M.
$246 nightly
The price is $261
Sep 20 - Sep 21
Total with taxes and fees
Deal Island Bay Cottage
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, (15 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$272 nightly
The price is $289
Sep 15 - Sep 16
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A wooden deck with a hot tub, lounge chairs, and a view of the water.

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

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$476 nightly
The price is $499
Sep 13 - Sep 14
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
A covered outdoor area with a table and chairs, surrounded by trees.

10. 8 Mi to Ocean City: Warm & Cozy 3BR Family Home

8 Mi to Ocean City: Warm & Cozy 3BR Family Home
3.0 star property
Ocean Pines
$536 nightly
The price is $600
Sep 30 - Oct 1
Total with taxes and fees
8 Mi to Ocean City: Warm & Cozy 3BR Family Home
A waterfront house with a balcony, dock, and a view of the water.

11. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (631 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
$242 nightly
The price is $272
Sep 13 - Sep 14
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.

12. 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, (61 reviews)
"We stayed at this property for 6 nights, everything was exactly like the pictures and very clean. We were just far enough to many shopping areas and grocery stores. It was very quiet and peaceful. Ed and Cindy are amazing hosts, we will be returning next year!"
United States
Haileigh
$200 nightly
The price is $204
Sep 15 - Sep 16
Total with taxes and fees
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
A two-story house with a red door, a front porch, and a tree in the foreground.

13. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
$313 nightly
The price is $351
Sep 16 - Sep 17
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

14. 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
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$241 nightly
The price is $266
Sep 10 - Sep 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.

15. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (61 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
$281 nightly
The price is $297
Sep 30 - Oct 1
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
A stone house with a red roof, surrounded by a well-maintained garden and trees.

16. Historic Cottage in West Chester PA - Two miles from town.

Historic Cottage in West Chester PA - Two miles from town.
West Chester
10.0 out of 10, Exceptional, (109 reviews)
"Our stay was perfect."
United States
Jodi H.
$265 nightly
The price is $293
Sep 17 - Sep 18
Total with taxes and fees
Historic Cottage in West Chester PA - Two miles from town.

17. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 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
$311 nightly
The price is $338
Oct 1 - Oct 2
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
A single-story house with a covered porch, a number '374' on the side, and a covered grill area.

18. 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, (25 reviews)
"loved our stay!"
United States
Clair H.
$340 nightly
The price is $347
Oct 6 - Oct 7
Total with taxes and fees
Charming 1-bedroom cottage with loft in Rehoboth Beach
A small, single-story building with a blue exterior and a metal roof, surrounded by a gravel driveway and a wooden fence.

19. Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens

Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
Kennett Square
10.0 out of 10, Exceptional, (8 reviews)
"It was everything we hoped it would be"
United States
Carla H.
$286 nightly
The price is $316
Sep 10 - Sep 11
Total with taxes and fees
Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
A blue house with a porch, white shutters, and a black railing.

20. Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (62 reviews)
"Great location, super clean and the host was very thoughtful with all the sweet treats provided for us. The coffee bar was well stocked and the kitchen had everything needed for our weekend stay."
United States
Tammy W.
$249 nightly
The price is $275
Sep 10 - Sep 11
Total with taxes and fees
Heart of Amish Country - Paradise Cottage
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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Top Eastern Shore Hotel Reviews

Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Muy bueno. Entre rapido y me gusto el cuarto solo que la puerta del baño no cierra la muchacha que me atendió fue amable y si volvería lo recomiendo esta enfrente la playa"
Joel 1-night trip
Posted less than an hour ago
Plim Plaza Hotel

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
998
Accommodation
27 Cottages
Lowest Price
$107
Highest Price
$600

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between $107 and $600 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 9.8. 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 27 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.

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