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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Eastern Shore cottages

A single-story mobile home with a front porch and steps leading to the entrance.

1. 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, (57 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
$326 nightly
The price is $365
Oct 11 - Oct 12
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

2. 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, (57 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
$199 nightly
The price is $210
Oct 11 - Oct 12
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A single-story house with a front porch, a staircase leading to the entrance, and a small deck.

3. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
$243 nightly
The price is $257
Oct 12 - Oct 13
Total with taxes and fees
Deal Island Bay Cottage
A wooden deck with a white railing overlooking a calm body of water and a distant bridge.

4. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
$923 nightly
The price is $1,034
Oct 18 - Oct 19
Total with taxes and fees
Game Room! Waterfront Group Haven in Ocean Pines
A waterfront house with a balcony, dock, and a view of the water.

5. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (655 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
$215 nightly
The price is $242
Oct 11 - Oct 12
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.

6. 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, (63 reviews)
$212 nightly
The price is $216
Oct 21 - Oct 22
Total with taxes and fees
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

7. 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.
$260 nightly
The price is $287
Oct 12 - Oct 13
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

8. 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, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$424 nightly
The price is $477
Oct 18 - Oct 19
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A single-story house with a covered porch, a number '374' on the side, and a covered grill area.

9. 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, (26 reviews)
"loved our stay!"
United States
Clair H.
$343 nightly
The price is $350
Oct 12 - Oct 13
Total with taxes and fees
Charming 1-bedroom cottage with loft in Rehoboth Beach
A house with a porch, a door, and two chairs.

10. 2 1/2 Mi to Bethany Boardwalk! Private Retreat!

2 1/2 Mi to Bethany Boardwalk! Private Retreat!
3.0 star property
Ocean View
$440 nightly
The price is $466
Oct 11 - Oct 12
Total with taxes and fees
2 1/2 Mi to Bethany Boardwalk! Private Retreat!
Welcome to Creekside Retreat!

11. 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 15 - Oct 16
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
A wooden deck leading to a house surrounded by dense trees.

12. Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (90 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
$316 nightly
The price is $349
Oct 11 - Oct 12
Total with taxes and fees
Cozy Spring House in Gorgeous Chadds Ford!
A small, single-story building with a blue exterior and a metal roof, surrounded by a gravel driveway and a wooden fence.

13. 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, (9 reviews)
$317 nightly
The price is $350
Oct 12 - Oct 13
Total with taxes and fees
Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
A wooden deck with wicker furniture, a round table, and a fire pit.

14. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Oct 12 - Oct 13
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A sunlit patio with wicker furniture, a potted plant, and a decorative rug.

15. Ocean Block Dewey Beach and Pet Friendly!

Ocean Block Dewey Beach and Pet Friendly!
Rehoboth by the Sea
10.0 out of 10, Exceptional, (197 reviews)
"Perfect for a quiet off season get away, would be even better in season. "
United States
Robert G.
$517 nightly
The price is $534
Nov 1 - Nov 2
Total with taxes and fees
Ocean Block Dewey Beach and Pet Friendly!
A single-story house with a front porch, a small deck, and a wooden walkway leading to the door.

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (20 reviews)
$398 nightly
The price is $440
Oct 26 - Oct 27
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
A two-story house with a deck, a barbecue grill, and a covered patio area.

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

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
$483 nightly
The price is $533
Oct 19 - Oct 20
Total with taxes and fees
Thunder Hill Retreat - Spacious/Deck/Hot tub
A blue house with a porch, white shutters, and a black railing.

18. Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (66 reviews)
"House was great Very clean Very comfortable and easy to get around the area. Host was very responsive and easy to work with"
United States
Jeannie K.
$249 nightly
The price is $275
Oct 13 - Oct 14
Total with taxes and fees
Heart of Amish Country - Paradise Cottage
Exterior

19. 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 15 - Oct 16
Total with taxes and fees
Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
A two-story house with a front porch, a satellite dish, and a mailbox.

20. 6 Mi to Inner Harbor - Family Home w/ Fenced Yard!

6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
3.0 star property
Westfield
10.0 out of 10, Exceptional, (1 review)
$340 nightly
The price is $399
Oct 12 - Oct 13
Total with taxes and fees
6 Mi to Inner Harbor - Family Home w/ Fenced Yard!
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
"Beautiful clean room right on the ocean! We will be returning!"
Tammy 4-night trip
Posted 13 hours ago
Princess Royale Oceanfront Resort
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 8 days ago
St Michaels Inn

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,575
Accommodation
27 Cottages
Lowest Price
$210
Highest Price
$1,034

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between $210 and $1,034 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 9.7. 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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