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Cottages in Eastern Shore

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
$124 nightly
The price is $138
Nov 9 - Nov 10
Total with taxes and fees
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.
$274 nightly
The price is $304
Nov 9 - Nov 10
Total with taxes and fees
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
$214 nightly
The price is $239
Nov 17 - Nov 18
Total with taxes and fees
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.
$201 nightly
The price is $213
Nov 9 - Nov 10
Total with taxes and fees
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, (27)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
United States
Chris S.
$199 nightly
The price is $210
Nov 9 - Nov 10
Total with taxes and fees
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)
$355 nightly
The price is $384
Nov 16 - Nov 17
Total with taxes and fees
#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.
$248 nightly
The price is $263
Nov 9 - Nov 10
Total with taxes and fees
Deal Island Bay Cottage
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.
$446 nightly
The price is $467
Nov 20 - Nov 21
Total with taxes and fees
Long Beach Cottage, (romantic couple’s getaway)
Exterior
Grandma’s Cottage will wrap around you like a warm hug

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

Betterton
$395 nightly
The price is $419
Nov 8 - Nov 9
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
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.
$802 nightly
The price is $885
Dec 1 - Dec 2
Total with taxes and fees
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
$134 nightly
The price is $151
Dec 1 - Dec 2
Total with taxes and fees
Key West Cottages
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.
$247 nightly
The price is $273
Nov 10 - Nov 11
Total with taxes and fees
Heart of Amish Country - Paradise Cottage
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.
$221 nightly
The price is $244
Nov 10 - Nov 11
Total with taxes and fees
Restful and Quaint Cottage
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.
$241 nightly
The price is $255
Nov 13 - Nov 14
Total with taxes and fees
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
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.
$265 nightly
The price is $281
Nov 9 - Nov 10
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
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
$399 nightly
The price is $460
Nov 16 - Nov 17
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
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.
$254 nightly
The price is $269
Nov 9 - Nov 10
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
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
$271 nightly
The price is $299
Nov 11 - Nov 12
Total with taxes and fees
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.
$313 nightly
The price is $346
Nov 30 - Dec 1
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior
Charming Carriage House in the Heart of Kennett

Charming Carriage House in the Heart of Kennett

Kennett Square
10.0 out of 10, Exceptional, (37)
"Booked and stayed it was a great little place to have while visiting family"
United States
Khadir V.
$401 nightly
The price is $443
Nov 10 - Nov 11
Total with taxes and fees
Charming Carriage House in the Heart of Kennett
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

Sahara Motel

Sahara Motel

10/10 Excellent
"They were close to the beach and boardwalk. Now our specific hotel was not on the beachfront side, etc. but it is also close to the Starbucks in OCMD. I loved the proximity. Clean room. Shower & Tub combo. Elevator to get stuff up and down to room. Clean bedding. The one downside was they don’t have any luggage carts so make that be something in mind when you’re packing the items up to go to the hotel. Have something to lug to and from hotel room. Hope this helps. "
kaitlynn 4-night trip
Posted 13 hours ago
Sahara Motel

Find out more about Eastern Shore

Eastern Shore Cottages information

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 Cottages
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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? 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 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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