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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Eastern Shore cottages

A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

1. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (383 reviews)
"Easy accessible"
United States
Melissa
$185 nightly
The price is $207
Oct 2 - Oct 3
Total with taxes and fees
Shore Point Cottages
A single-story mobile home with a front porch, a small staircase, and a covered outdoor area.

2. Pool + Bay Access! Home 13 Mi to Ocean City Beach

Pool + Bay Access! Home 13 Mi to Ocean City Beach
3.0 star property
Ocean Pines
$382 nightly
The price is $428
Sep 28 - Sep 29
Total with taxes and fees
Pool + Bay Access! Home 13 Mi to Ocean City Beach
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, (56 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
$305 nightly
The price is $342
Sep 29 - Sep 30
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.

4. 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.
$196 nightly
The price is $207
Sep 28 - Sep 29
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.

5. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 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.
$235 nightly
The price is $249
Oct 1 - Oct 2
Total with taxes and fees
Deal Island Bay Cottage
A residential area with houses, a parking lot, and a body of water in the background.

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.
$215 nightly
The price is $228
Sep 29 - Sep 30
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A wooden deck with a hot tub, lounge chairs, and a view of the water.

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

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
$497 nightly
The price is $521
Oct 22 - Oct 23
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
A lakeside property with a large house, a shed, and a dense forest in the background.

8. 'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
'the Bayside Escape' Remote Chesapeake Bay Estate
A wooden deck with a white railing overlooking a calm body of water and a distant bridge.

9. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
$1,074 nightly
The price is $1,203
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.

10. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (648 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
$224 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
Key West Cottages
A two-story house with a red door, a front porch, and a tree in the foreground.

11. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
$304 nightly
The price is $341
Sep 30 - Oct 1
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

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.
$266 nightly
The price is $296
Oct 5 - Oct 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

13. 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.
$233 nightly
The price is $258
Sep 28 - Sep 29
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

14. 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
$195 nightly
The price is $199
Oct 8 - Oct 9
Total with taxes and fees
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

15. 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.
$265 nightly
The price is $281
Oct 27 - Oct 28
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay

16. 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
$295 nightly
The price is $320
Sep 28 - Sep 29
Total with taxes and fees
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.

17. 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.
$322 nightly
The price is $329
Sep 28 - Sep 29
Total with taxes and fees
Charming 1-bedroom cottage with loft in Rehoboth Beach
A small, single-story building with a blue exterior and a metal roof, surrounded by a gravel driveway and a wooden fence.

18. 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, (8 reviews)
"It was everything we hoped it would be"
United States
Carla H.
$291 nightly
The price is $322
Sep 28 - Sep 29
Total with taxes and fees
Blue Lotus Cottage, Walk to Downtown Kennett Square, Near Longwood Gardens
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, (65 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.
$238 nightly
The price is $263
Sep 28 - Sep 29
Total with taxes and fees
Heart of Amish Country - Paradise Cottage
A wooden deck leading to a house surrounded by dense trees.

20. Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (89 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
$300 nightly
The price is $332
Sep 28 - Sep 29
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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"Good"
Rosemary 4-night trip
Posted 4 hours ago
Grand Hotel Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,731
Accommodation
27 Cottages
Lowest Price
$199
Highest Price
$1,203

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between $199 and $1,203 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 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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