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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Eastern Shore cottages

A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

1. 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)
"Unique charming place to relax."
United States
Nimia N.
The price is CA $250
CA $300 total
includes taxes & fees
Oct 19 - Oct 20
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.

2. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
The price is CA $199
CA $370 total
includes taxes & fees
Oct 15 - Oct 16
Deal Island Bay Cottage
A single-story mobile home with a front porch and steps leading to the entrance.

3. 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, (58 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
The price is CA $192
CA $516 total
includes taxes & fees
Oct 15 - Oct 16
Comfortable cottage in gated community, 5 mins to OC and Assateague
A residential area with houses, a parking lot, and a body of water in the background.

4. 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 CA $211
CA $332 total
includes taxes & fees
Nov 9 - Nov 10
Quarry Landing - Center of Town & River View - 3 Bedroom
A wooden deck with a white railing overlooking a calm body of water and a distant bridge.

5. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
The price is CA $580
CA $1,432 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines
A waterfront house with a balcony, dock, and a view of the water.

6. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (658 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $276
CA $310 total
includes taxes & fees
Oct 14 - Oct 15
Key West Cottages
A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

7. 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)
"The suite was very clean and our two children greatly enjoyed the pool!"
United States
Kay Lorelle R.
The price is CA $128
CA $308 total
includes taxes & fees
Oct 22 - Oct 23
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.

8. 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 CA $218
CA $379 total
includes taxes & fees
Oct 14 - Oct 15
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.

9. 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.
The price is CA $402
CA $608 total
includes taxes & fees
Nov 5 - Nov 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A covered patio with a table and chairs, a white fence, and a view of the greenery.

10. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
The price is CA $214
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
Getaway on 1/2 Acre w/ Deck in Georgetown
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
The price is CA $228
CA $478 total
includes taxes & fees
Oct 22 - Oct 23
Pet-friendly creekside cottage w/ backyard
A single-story house with a covered porch, a number '374' on the side, and a covered grill area.

12. 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.
The price is CA $214
CA $497 total
includes taxes & fees
Nov 3 - Nov 4
Charming 1-bedroom cottage with loft in Rehoboth Beach
A wooden deck leading to a house surrounded by dense trees.

13. 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.
The price is CA $285
CA $502 total
includes taxes & fees
Nov 3 - Nov 4
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.

14. 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, (10 reviews)
"It was everything we hoped it would be"
United States
Carla H.
The price is CA $262
CA $500 total
includes taxes & fees
Oct 14 - Oct 15
Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

15. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $465
CA $820 total
includes taxes & fees
Oct 18 - Oct 19
Plum Point Cottage #15
A wooden deck with wicker furniture, a round table, and a fire pit.

16. 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.
The price is CA $514
CA $949 total
includes taxes & fees
Oct 14 - Oct 15
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A sunlit patio with wicker furniture, a potted plant, and a decorative rug.

17. Ocean Block Dewey Beach and Pet Friendly!

Ocean Block Dewey Beach and Pet Friendly!
Rehoboth by the Sea
10.0 out of 10, Exceptional, (198 reviews)
"Perfect for a quiet off season get away, would be even better in season. "
United States
Robert G.
The price is CA $356
CA $763 total
includes taxes & fees
Nov 3 - Nov 4
Ocean Block Dewey Beach and Pet Friendly!
A covered patio with a table and chairs, large windows, and an American flag.

18. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $389
CA $654 total
includes taxes & fees
Oct 16 - Oct 17
Plum Point Cottage #17
A blue house with a porch, white shutters, and a black railing.

19. Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (67 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.
The price is CA $190
CA $392 total
includes taxes & fees
Oct 19 - Oct 20
Heart of Amish Country - Paradise Cottage
A two-story house with a wooden deck, a garage, and a shed in the backyard.

20. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is CA $368
CA $439 total
includes taxes & fees
Oct 18 - Oct 19
Lakefront Home Firepit BWI Marleycreek River
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 Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"The 1st room we checked into had an odd smell to it. The woman at the front desk was very helpful and was able to get us a new room right away."
Brian 2-night trip
Posted 1 hour ago
Princess Bayside Beach Hotel

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,556
Accommodation
27 Cottages
Lowest Price
CA $300
Highest Price
CA $1,432

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between CA $300 and CA $1,432 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? Travellers 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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