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

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
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
The price is £270
includes taxes & fees
22 Sept - 23 Sept
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.
The price is £161
includes taxes & fees
21 Sept - 22 Sept
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)
"Just a really nice little place and we loved it! Clean, convenient, and it had everything we need! We will come back!"
United States
Mark F.
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.
The price is £201
includes taxes & fees
21 Sept - 22 Sept
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.
The price is £160
includes taxes & fees
24 Sept - 25 Sept
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.
The price is £349
includes taxes & fees
22 Sept - 23 Sept
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, (642 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is £169
includes taxes & fees
18 Oct - 19 Oct
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, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is £232
includes taxes & fees
30 Sept - 1 Oct
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
The price is £165
includes taxes & fees
11 Oct - 12 Oct
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.
The price is £197
includes taxes & fees
21 Sept - 22 Sept
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.
The price is £239
includes taxes & fees
5 Oct - 6 Oct
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
The price is £302
includes taxes & fees
26 Sept - 27 Sept
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
The price is £254
includes taxes & fees
21 Sept - 22 Sept
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, (64 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.
The price is £196
includes taxes & fees
21 Sept - 22 Sept
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.
The price is £250
includes taxes & fees
20 Oct - 21 Oct
Charming 1-bedroom cottage with loft in Rehoboth Beach
TV

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
The price is £234
includes taxes & fees
1 Oct - 2 Oct
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.
The price is £366
includes taxes & fees
21 Sept - 22 Sept
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.
The price is £265
includes taxes & fees
21 Sept - 22 Sept
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.
The price is £318
includes taxes & fees
13 Oct - 14 Oct
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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"It was honestly very relaxing! Will book here again!"
Beatriz 2-night trip
Posted 3 hours ago
Princess Royale Oceanfront Resort

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,394
Accommodation
28 Cottages
Lowest Price
£160
Highest Price
£366

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between £160 and £366 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 an escape to Ocean City? Travellers love Frontier Town Campground, a 2-star property with a swimming pool and a barbecue grill. Another in-demand choice where you can escape the daily grind is 103 79th Street 3 Bedroom Cottage By Redawning. It has a 3-star rating and conveniences including a patio and a nearby beach.
How many cottages are there in Eastern Shore?
Take your pick of 28 cottages in Eastern Shore. Whether you're travelling 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?
You can find family-friendly cottages in destinations around Eastern Shore, including Ocean City. Frontier Town Campground is one property that'll suit your needs in this popular city. It has a 2-star rating and conveniences like a playground and a barbecue grill. Alternatively, enjoy the comfy surrounds of 103 79th Street 3 Bedroom Cottage By Redawning. With WiFi and clothes washing facilities, this 3-star cottage in Ocean City will make your crew feel welcome. You'll discover lots of fantastic things to do with your team in Ocean City. Assateague State Park and Golf Down Under promise a superb day out.
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 traveller 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 holiday 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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