A marina with numerous boats docked at wooden piers under a clear sky.

Search Eastern Shore Cottage Rentals from CA $295

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Eastern Shore cottages

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
9.8 out of 10, Exceptional, (49 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is CA $246
CA $295 total
includes taxes & fees
Jul 22 - Jul 23
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (60 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is CA $223
CA $397 total
includes taxes & fees
Aug 2 - Aug 3
Deal Island Bay Cottage
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
The price is CA $185
CA $380 total
includes taxes & fees
Aug 9 - Aug 10
6 Mi to Salisbury: Forest-view Sanctuary!
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, (51 reviews)
"Great accomodations!"
United States
Linda S.
The price is CA $316
CA $675 total
includes taxes & fees
Jul 26 - Jul 27
Comfortable cottage in gated community, 5 mins to OC and Assateague
Property grounds

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, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is CA $308
CA $448 total
includes taxes & fees
Jul 19 - Jul 20
Quarry Landing - Center of Town & River View - 3 Bedroom
Terrace/patio

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is CA $715
CA $1,027 total
includes taxes & fees
Aug 11 - Aug 12
Long Beach Cottage, (romantic couple’s getaway)
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is CA $639
CA $1,281 total
includes taxes & fees
Jul 29 - Jul 30
'the Bayside Escape' Remote Chesapeake Bay Estate
Palm Cottage

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (599 reviews)
"Beautiful family friendly place. Great pool. Great location."
United States
KRYSTLE
The price is CA $430
CA $483 total
includes taxes & fees
Aug 18 - Aug 19
Key West Cottages
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is CA $215
CA $447 total
includes taxes & fees
Aug 11 - Aug 12
Soul Oasis - home on the Chesapeake Bay
Property grounds

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, (10 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is CA $215
CA $376 total
includes taxes & fees
Jul 20 - Jul 21
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

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, (52 reviews)
"The place was extremely nice but the could not sleep on that bed again. Sinks way down like you are in two hammocks with a big lump in the middle. May work for some people but we couldn’t sleep. Other than that extremely nice and very well stocked. Good location to sports on the Beach complex for tournaments."
United States
Walter
The price is CA $232
CA $410 total
includes taxes & fees
Jul 29 - Jul 30
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
House (3 Bedrooms) | Interior

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 $218
CA $475 total
includes taxes & fees
Jul 29 - Jul 30
Getaway on 1/2 Acre w/ Deck in Georgetown
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, (52 reviews)
"The house was perfect for my family's needs for our stay. It was clean, quiet, and cozy. The owner was incredibly kind and gracious and incredibly helpful."
United States
Andrew C.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior

Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (61 reviews)
"The host was friendly and helpful. The cottage was very nice"
United States
David F.
The price is CA $186
CA $385 total
includes taxes & fees
Jul 22 - Jul 23
Heart of Amish Country - Paradise Cottage
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
9.6 out of 10, Exceptional, (17 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is CA $298
CA $591 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior

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, (19 reviews)
"Very cute, clean and cozy and had everything we needed. Quiet location but, only a short distance from all we wanted to go to.."
United States
Jody M.
The price is CA $353
CA $655 total
includes taxes & fees
Aug 16 - Aug 17
Charming 1-bedroom cottage with loft in Rehoboth Beach
Property grounds

Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (83 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
The price is CA $316
CA $534 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Spring House in Gorgeous Chadds Ford!
Exterior

Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Everything was good. Had a great time."
United States
Todd H.
The price is CA $438
CA $880 total
includes taxes & fees
Aug 6 - Aug 7
Thunder Hill Retreat - Spacious/Deck/Hot tub
Property grounds

Slps 8 - Comm. Pool - PetsOK - WD - King - Bikes

Slps 8 - Comm. Pool - PetsOK - WD - King - Bikes
Lewes
9.4 out of 10, Exceptional, (8 reviews)
"Great stay!"
United States
Ashley Z.
The price is CA $455
CA $782 total
includes taxes & fees
Jul 23 - Jul 24
Slps 8 - Comm. Pool - PetsOK - WD - King - Bikes
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Eastern Shore Hotel Reviews

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"It’s close to everything, has a restaurant, pool ,clean, spacious rooms. Staff at front desk was very friendly and welcoming,"
Karen 3-night trip
Posted less than an hour ago
Days Inn by Wyndham Ocean City Oceanfront

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews
1,102
Accommodation
28 Cottages
Lowest Price
CA $295
Highest Price
CA $1,281

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between CA $295 and CA $1,281 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 28 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.

Explore a world of travel with Expedia