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Our top choices for Eastern Shore cottages

Deluxe Cottage | View from room
Shore Point Cottages

Cottage in Berlin

Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, (300)
"Was a great place to bring kids and dogs! "
United States
AMANDA
$122 nightly
The price is $137
Jan 19 - Jan 20, 2026
Total with taxes and fees
Shore Point Cottages
Exterior
Comfortable cottage in gated community, 5 mins to OC and Assateague

Cottage in Assateague Pointe

Comfortable cottage in gated community, 5 mins to OC and Assateague
9.8 out of 10, Exceptional, (43)
"This was the perfect little home for our stay. Everything was clean and comfortable and “cozy”. The location was wonderful with easy access to both Assateague Island and Ocean City. Everything needed for a great stay was provided. We are already planning our vacation for next year and will definitely book again. "
United States
Alecia C.
$286 nightly
The price is $317
Jan 4 - Jan 5, 2026
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
House (3 Bedrooms) | Outdoor dining
6 Mi to Salisbury: Forest-view Sanctuary!

Cottage in Parsonsburg

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
$230 nightly
The price is $257
Dec 20 - Dec 21
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
Property grounds
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Cottage in Port Deposit

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (31)
"The River Cottage is very charming, cozy, and well-stocked with all the essentials. The host is quick to respond to inquiries. We had a wonderful and relaxing stay!"
United States
Xiaodong F.
$196 nightly
The price is $207
Dec 21 - Dec 22
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Cottage in Port Deposit

Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
$201 nightly
The price is $213
Jan 5 - Jan 6, 2026
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior
Deal Island Bay Cottage

Cottage in Deal Island

Deal Island Bay Cottage
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$248 nightly
The price is $263
Dec 20 - Dec 21
Total with taxes and fees
Deal Island Bay Cottage
Exterior
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
$395 nightly
The price is $419
Dec 30 - Dec 31
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
Long Beach Cottage, (romantic couple’s getaway)

Cottage in Charlestown

Long Beach Cottage, (romantic couple’s getaway)
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
$427 nightly
The price is $447
Dec 23 - Dec 24
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Property grounds
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 22 - Dec 23
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Palm Cottage | 1 bedroom, premium bedding, individually decorated
Key West Cottages

Cottage in Downtown Chincoteague

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (488)
"We love Key West Cottages!"
United States
Jonathan
$111 nightly
The price is $125
Dec 21 - Dec 22
Total with taxes and fees
Key West Cottages
Exterior
Heart of Amish Country - Paradise Cottage

Cottage in Paradise

Heart of Amish Country - Paradise Cottage
10.0 out of 10, Exceptional, (43)
"We absolutely loved everything about our stay at Ruth Ann's charming home! The warm, welcoming home was just what we needed for our getaway. "
United States
Andrea S.
$247 nightly
The price is $273
Dec 20 - Dec 21
Total with taxes and fees
Heart of Amish Country - Paradise Cottage
Exterior
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (39)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
$252 nightly
The price is $267
Dec 22 - Dec 23
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Property grounds
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Cottage in Owings

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
$243 nightly
The price is $257
Dec 21 - Dec 22
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
$431 nightly
The price is $498
Dec 21 - Dec 22
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Property grounds
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage in Benedict

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
$271 nightly
The price is $299
Dec 20 - Dec 21
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Outdoor spa tub
Restful and Quaint Cottage

Cottage in Conestoga

Restful and Quaint Cottage
9.8 out of 10, Exceptional, (126)
"We loved staying in this cottage. It is in a quiet location. Loved the hot tub. "
United States
Anonymous traveler
$313 nightly
The price is $345
Dec 22 - Dec 23
Total with taxes and fees
Restful and Quaint Cottage
Exterior
Charming Carriage House in the Heart of Kennett

Cottage in Kennett Square

Charming Carriage House in the Heart of Kennett
10.0 out of 10, Exceptional, (37)
"Just what we were hoping for."
United States
Anonymous traveler
$400 nightly
The price is $442
Dec 22 - Dec 23
Total with taxes and fees
Charming Carriage House in the Heart of Kennett
Exterior
Charming 1-bedroom cottage with loft in Rehoboth Beach

Cottage in Truitts Park

Charming 1-bedroom cottage with loft in Rehoboth Beach
9.8 out of 10, Exceptional, (15)
"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.
$339 nightly
The price is $346
Dec 20 - Dec 21
Total with taxes and fees
Charming 1-bedroom cottage with loft in Rehoboth Beach
Exterior
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Point Lookout

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.4 out of 10, Exceptional, (8)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
$295 nightly
The price is $326
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Property grounds
Cozy Spring House in Gorgeous Chadds Ford!

Cottage in Chadds Ford

Cozy Spring House in Gorgeous Chadds Ford!
10.0 out of 10, Exceptional, (67)
"Comfy, clean and comfortable. Would stay here again. Great location, location, location."
United States
Stephen D.
$316 nightly
The price is $343
Jan 4 - Jan 5, 2026
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.
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Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"Super clean. Friendly staffs"
Patcharaporn 2-night trip
Posted 3 days ago
Holiday Inn & Suites Ocean City by IHG

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,318
Accommodation
61 Cottages
Lowest Price
$125
Highest Price
$885

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between $125 and $885 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 9.6. 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 61 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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