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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Kennedyville and around

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Outdoor dining

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Exterior

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Eastern Shore beach cottage get-away
Exterior

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
Charming, updated 1930's beachfront cottage with stunning sunset views
Interior

Charming, updated 1930's beachfront cottage with stunning sunset views

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Charming, updated 1930's beachfront cottage with stunning sunset views
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Outdoor dining

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (19)
"Very nice cottage, as advertised"
The price is €181
includes taxes & fees
1 Sept - 2 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Terrace/patio

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (12)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Peaceful getaway convenient to local amenities including beach, boating & food
Exterior

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (116)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Sunset River Shack -amazing waterfront view
Property grounds

Sunset River Shack -amazing waterfront view

2.0 star property
9.4 out of 10, Exceptional, (3)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
Sunset River Shack -amazing waterfront view
Waterfront cottage in historic Charlestown, Maryland
Exterior

Waterfront cottage in historic Charlestown, Maryland

9.8 out of 10, Exceptional, (8)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
Waterfront Cottage on the C&D Canal!
Exterior

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!
Walk to Town & River: Charming Home in North East!
House (3 Bedrooms) | Interior

Walk to Town & River: Charming Home in North East!

3.0 star property
Walk to Town & River: Charming Home in North East!
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds

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

9.8 out of 10, Exceptional, (7)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
The price is €252
includes taxes & fees
20 Aug - 21 Aug
Quarry Landing - Center of Town & River View - 3 Bedroom
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (2)
"Adorable little cottage and amenities. Owners very nice. Perfect little getaway. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Beach towels

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (11)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Exterior

3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor

9.4 out of 10, Exceptional, (6)
"Thanks Gwendolyn… we had a great time!"
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Waterfront Historical District Home Near River
House (3 Bedrooms) | Interior

Waterfront Historical District Home Near River

3.0 star property
10.0 out of 10, Exceptional, (2)
"The home was beautiful and well kept. Essential kitchen items are included along with sheets and towels. The host was a super reliable. Communication was wonderful. The host had toiletries and some stocked snacks for the guests. There were corn hole boards and ladder ball for guests to use. The home is about a block to the river where fishing is a must. There is also a public beach within walking distance. "
Waterfront Historical District Home Near River
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
The price is €548
includes taxes & fees
31 Aug - 1 Sept
Long Beach Cottage, (romantic couple’s getaway)
Vintage Waterfront Cottage with Stunning Sunsets
Terrace/patio

Vintage Waterfront Cottage with Stunning Sunsets

10.0 out of 10, Exceptional, (5)
"This was a perfect spot for a quick getaway for my husband and I! The house is lovely with plenty of charm, a well-appointed kitchen and comfortable furniture. The yard is lovely and it’s just a short walk to the private beach to bird watch or just take a stroll. Would highly recommend!"
Vintage Waterfront Cottage with Stunning Sunsets
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.2 out of 10, Wonderful, (10)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
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 Kennedyville Hotel Reviews

Red Roof Inn Perryville

Red Roof Inn Perryville

10/10 Excellent
"It was recently renovated. "
Jeremiah 1-night trip
Posted 23 hours ago
Red Roof Inn Perryville

Frequently asked questions

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Reserving a cottage in Kennedyville is as simple as clicking on your travel dates and picking your ideal place for a holiday in the outdoors. From upmarket retreats to inexpensive properties and cottages that have perks like a pool, Expedia has something for all styles and tastes. As for the best deals around? We've have them as well!
How can I find cheap cottages in Kennedyville?
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What is there to do in Kennedyville near my cottage?
Once you've settled into your hotel, head out and explore the wonderful things Kennedyville has to offer. Crow Farm and Vineyard is a top attraction to add to your travel itinerary.