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Check prices for these dates

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14 Nov - 16 Nov
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21 Nov - 23 Nov
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5 Dec - 7 Dec
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Featured Cottages in Eastern Shore and around

Deluxe Cottage | View from room
Shore Point Cottages

Shore Point Cottages

3.0 star property
Berlin
9.4 out of 10, Exceptional, (297)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages
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, (43)
"This is a beautiful clean modern home."
United States
Toni R.
The price is €271
includes taxes & fees
10 Nov - 11 Nov
Comfortable cottage in gated community, 5 mins to OC and Assateague
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!
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
9.8 out of 10, Exceptional, (10)
"Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable."
United States
Geoff F.
The price is €189
includes taxes & fees
9 Nov - 10 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom
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, (28)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
United States
Chris S.
The price is €187
includes taxes & fees
18 Nov - 19 Nov
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior
#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
The price is €341
includes taxes & fees
21 Nov - 22 Nov
#2 Egret Cottage Harris Cove
Exterior
Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
9.6 out of 10, Exceptional, (57)
"Very nice house and close enough to go places but far enough to be peaceful."
United States
Larry F.
The price is €234
includes taxes & fees
9 Nov - 10 Nov
Deal Island Bay Cottage
Exterior
Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is €374
includes taxes & fees
9 Nov - 10 Nov
Grandma’s Cottage will wrap around you like a warm hug
Outdoor spa tub
Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)

Charlestown
10.0 out of 10, Exceptional, (4)
"We had a fantastic time. Beautiful, clean, and all the comforts of home. Loved the beach and swimming in front of the property! We didn’t get to use the hot tub, kayaks and paddle boats but it’s wonderful to have for those who would like them, or if we had more time. We love the Wellwood and Backfin Blues for dining. Dave and Barb are wonderful hosts that reached out during stay. I would highly recommend this lovely cottage. Thank you for hosting us! "
United States
Nancy R.
The price is €414
includes taxes & fees
20 Nov - 21 Nov
Long Beach Cottage, (romantic couple’s getaway)
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is €785
includes taxes & fees
8 Dec - 9 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (475)
"Amazing place for vacation "
United States
carla
Key West Cottages
Exterior
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Lusby
9.8 out of 10, Exceptional, (36)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is €249
includes taxes & fees
9 Nov - 10 Nov
Soul Oasis - home on the Chesapeake Bay
Property grounds
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
The price is €226
includes taxes & fees
13 Nov - 14 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor dining
Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage

Paradise
10.0 out of 10, Exceptional, (40)
"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.
The price is €242
includes taxes & fees
10 Nov - 11 Nov
Heart of Amish Country - Paradise Cottage
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
The price is €398
includes taxes & fees
17 Nov - 18 Nov
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Outdoor spa tub
Restful and Quaint Cottage

Restful and Quaint Cottage

Conestoga
9.8 out of 10, Exceptional, (124)
"Loved the house and the fact it had everything you could need during your stay!"
United States
Kaci P.
The price is €216
includes taxes & fees
10 Nov - 11 Nov
Restful and Quaint Cottage
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
10.0 out of 10, Exceptional, (1)
"Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! "
United States
Georgina P.
The price is €238
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Exterior
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Up the Neck
9.4 out of 10, Exceptional, (136)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is €315
includes taxes & fees
11 Nov - 12 Nov
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Terrace/patio
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, (6)
"Sophia the host is super attentive and responsive"
United States
Mayela
The price is €265
includes taxes & fees
11 Nov - 12 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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

Point Lookout
9.4 out of 10, Exceptional, (8)
"I had a wonderful stay at this cozy waterfront cottage. The listing was accurate, and the serene setting made for a relaxing getaway. The home was clean, well-equipped, and the views were stunning. We especially enjoyed watching the deer and fiddler crabs. Highly recommend for a peaceful retreat."
United States
Antwoine S.
The price is €315
includes taxes & fees
30 Nov - 1 Dec
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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
"The suite was beautiful and very clean. The amenities were excellent. A great location and a beautiful view. "
Robin 2-night trip
Posted 5 days ago
Holiday Inn & Suites Ocean City by IHG

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between and 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 . 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 cottages in Eastern Shore. Whether you're travelling 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 traveller 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 holiday 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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