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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Eastern Shore cottages

Cottage (2 Bedrooms) | Interior

1. 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
$211 nightly
The price is $235
Sep 18 - Sep 19
Total with taxes and fees
Pet-friendly Smith Island Cottage w/ Golf Cart!
Exterior

2. 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
$324 nightly
The price is $363
Sep 22 - Sep 23
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

3. 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, (53 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 20 - Sep 21
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

4. 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)
"The Castaway house was a wonderful spot for our family of 4. The house was so comfortable and it was fantastic to have access to the golf cart to tour the island!! The island was very welcoming. One highlight was a boat tour with Capt. Mark Kitching (410)603-1227. He took us through the marshes and outer islands, pointing out lots of birds (we saw Pelicans!!). Bring your own food if you want to cook- restaurants close early and groceries are limited. Cash or check for the boat over. It...
United States
Laura J.
$216 nightly
The price is $238
Sep 18 - Sep 19
Total with taxes and fees
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Exterior

5. 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.
$243 nightly
The price is $257
Oct 1 - Oct 2
Total with taxes and fees
Deal Island Bay Cottage
Property grounds

6. 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, (17 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$201 nightly
The price is $213
Sep 24 - Sep 25
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Terrace/patio

7. 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.
$536 nightly
The price is $562
Sep 22 - Sep 23
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Palm Cottage | 1 bedroom, premium bedding, laptop workspace, soundproofing

8. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (639 reviews)
"This was the perfect relaxing get away! Clean and quiet! Already booked for next spring 2027!"
United States
LaTonya
$224 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
Key West Cottages
Exterior

9. 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.
$277 nightly
The price is $294
Sep 30 - Oct 1
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Exterior

10. 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, (62 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
$212 nightly
The price is $217
Oct 11 - Oct 12
Total with taxes and fees
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Property grounds

11. 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 19 - Sep 20
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

12. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$433 nightly
The price is $487
Oct 5 - Oct 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
House (3 Bedrooms) | Interior

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

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
$359 nightly
The price is $403
Sep 26 - Sep 27
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Exterior

14. 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
$312 nightly
The price is $339
Oct 1 - Oct 2
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
Exterior

15. Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (63 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.
$236 nightly
The price is $261
Sep 21 - Sep 22
Total with taxes and fees
Heart of Amish Country - Paradise Cottage
Exterior

16. 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.
$350 nightly
The price is $357
Oct 12 - Oct 13
Total with taxes and fees
Charming 1-bedroom cottage with loft in Rehoboth Beach
Living area

17. Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA

Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
Up the Neck
$294 nightly
The price is $316
Oct 1 - Oct 2
Total with taxes and fees
Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
Exterior

18. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
$430 nightly
The price is $475
Sep 21 - Sep 22
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
Property grounds

19. Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (87 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
$316 nightly
The price is $349
Sep 20 - Sep 21
Total with taxes and fees
Cozy Spring House in Gorgeous Chadds Ford!
Exterior

20. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (18 reviews)
"Was very cozy and comfortable."
United States
sandi c.
$392 nightly
The price is $433
Oct 13 - Oct 14
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"The room was very cleaned. The staff, the bed and pillows were great. Great view from the balcony of the oceanfront. The restaurant on the property had great service and food."
Mary 3-night trip
Posted 8 hours ago
Days Inn by Wyndham Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,388
Accommodation
27 Cottages
Lowest Price
$210
Highest Price
$562

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between $210 and $562 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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