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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Eastern Shore cottages

House (3 Bedrooms) | Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
6 Mi to Salisbury: Forest-view Sanctuary!
Exterior

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, (45 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
Deal Island Bay Cottage
Exterior

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
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Terrace/patio

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

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, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
Quarry Landing - Center of Town & River View - 3 Bedroom
Palm Cottage | 1 bedroom, premium bedding, individually decorated

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (551 reviews)
"Such a nice spot, we’ll be back!"
United States
Jay
Key West Cottages
House (3 Bedrooms) | Interior

3 Mi to Dover Motor Speedway: Pet-friendly Retreat

3 Mi to Dover Motor Speedway: Pet-friendly Retreat
3.0 star property
Dover
3 Mi to Dover Motor Speedway: Pet-friendly Retreat
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
Soul Oasis - home on the Chesapeake Bay
Outdoor spa tub

Restful and Quaint Cottage

Restful and Quaint Cottage
Conestoga
9.8 out of 10, Exceptional, (131 reviews)
"It was so peaceful and had plenty of room for me and my friends to have my bachelorette weekend! Everything was so cute and easily accessible!"
United States
Emily S.
Restful and Quaint Cottage
Property grounds

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, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

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, (47 reviews)
"Great location, peaceful, clean, quaint & accommodating hosts"
United States
Michelle T.
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Exterior

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, (15 reviews)
"Very cute, clean and cozy and had everything we needed. Quiet location but, only a short distance from all we wanted to go to.."
United States
Jody M.
Charming 1-bedroom cottage with loft in Rehoboth Beach
Exterior

Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (52 reviews)
"Very pleasant host, very clean and very comfortable beds"
United States
Kathy P.
Heart of Amish Country - Paradise Cottage
Exterior

Cozy cottage w/ creekside patio & fire pit

Cozy cottage w/ creekside patio & fire pit
Up the Neck
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
Cozy cottage w/ creekside patio & fire pit
Exterior

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
Cottage Located on the Patuxent River!
Property grounds

Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (76 reviews)
"We had a wonderful stay! The home was cozy with lots of amenities. The interior is historic and simply gorgeous. Highly recommend and looking forward to staying again!"
United States
Lauren
Cozy Spring House in Gorgeous Chadds Ford!
House (4 Bedrooms) | Interior

1 Mi to Resort Marina! Greenbackville Retreat

1 Mi to Resort Marina! Greenbackville Retreat
3.0 star property
Captain's Cove
1 Mi to Resort Marina! Greenbackville Retreat
Interior

Ocean Block Dewey Beach and Pet Friendly!

Ocean Block Dewey Beach and Pet Friendly!
Rehoboth by the Sea
10.0 out of 10, Exceptional, (189 reviews)
"Perfect for a quiet off season get away, would be even better in season. "
United States
Robert G.
Ocean Block Dewey Beach and Pet Friendly!
Property grounds

Charming Farm Cottage

Charming Farm Cottage
Jarrettsville
Charming Farm 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

Quality Inn Oceanfront

Quality Inn Oceanfront

6/10 Okay
"The hotel was decent enough however, it was over priced in general. It could use some upgrading. Water didn’t get warm in the shower. Wanted to have late check out but it was ridiculously pricey."
Stacy 1-night trip
Posted 5 hours ago
Quality Inn Oceanfront

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between SAR 773 and SAR 1,807 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 32 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.
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.