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Compare 29 Cottages in Kennedyville with updated reviews, rates, and availability.

Be persuaded to experience this vintage cottage by the Sassa
9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (96)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Quarry Landing - Center of Town & River View - 3 Bedroom
9.8 out of 10, Exceptional, (7)
"On a small hillside. Very quaint accommodation. Close to restaurants and river. Parking a little difficult to figure out, train is a bit loud and frequent but everything else was as advertised and nice. "
The price is SAR 515
SAR 824 total
includes taxes & fees
7 Nov 2024 - 8 Nov 2024
Quarry Landing - Center of Town & River View - 3 Bedroom
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (132)
"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
Chesapeake Romantic Waterfront Home with Private Pool
8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
Waterfront Cottage on the C&D Canal!
7.6 out of 10, Good, (4)
"Awesome"
Waterfront Cottage on the C&D Canal!
Waterfront cottage in historic Charlestown, Maryland
10.0 out of 10, Exceptional, (3)
"Such a charming property and town. We loved everything about it!"
Waterfront cottage in historic Charlestown, Maryland
Vintage Waterfront Cottage with Stunning Sunsets
10.0 out of 10, Exceptional, (5)
"thoroughly enjoyed our time at this lovely property. the quiet location, attention to detail, and communication with owners all made for an delightful stay. "
Vintage Waterfront Cottage with Stunning Sunsets
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
10.0 out of 10, Exceptional, (5)
"My friend and I wanted to meet up part way between our two cities, and when we decided on the Chesapeake Bay, Rock Hall seemed a good option, and we were right! What a great little town, and the house was just perfect for us. She brought her two little ones (6 and 2), and I was on my own. I think with just 1 bathroom, many more than that would really not be ideal. The whole stay was great, we both agreed we'd love to come back again. The only hiccup (and I am sure it will be fixed), was that...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront Historical District Home Near River
3.0 star property
Waterfront Historical District Home Near River
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
8.0 out of 10, Very Good, (11)
"This was our second visit to Bayburst Lodge and it was even better than our first! We spent an entire week this time and it really was relaxing and quite enjoyable. We did a lot of fishing this trip. We caught huge catfish off the beach behind the house, and also did a 4 hour charter in which we caught our limit in Striped Bass. The weather was incredible and we spent a lot of time walking, shopping, and sitting on the screened porch. We tried a new restaurant called Ark and Dove this trip....
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Eastern Shore Getaway: Walk to Tolchester Marina!
3.0 star property
Eastern Shore Getaway: Walk to Tolchester Marina!
Private cottage
Private cottage
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
9.6 out of 10, Exceptional, (5)
"It was as advertised. It was clean and we had everything we needed. It was a very pleasant visit."
3B/1FB/Kitchen, Center of Town, The Cottage @ the Manor
Charming 2-bedroom water oriented cottage with water access
Charming 2-bedroom water oriented cottage with water access
Long Beach Cottage, (romantic couple’s getaway)
10.0 out of 10, Exceptional, (3)
"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"
Long Beach Cottage, (romantic couple’s getaway)
Sunset River Shack - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
2.0 star property
9.0 out of 10, Wonderful, (2)
"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 - Waterfront Boho Cottage on the Elk River /Chesapeake Bay
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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Other property types in Kennedyville

Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (18)
"Another amazing stay at Robin’s Rest. Highly recommend for a quiet weekend getaway "
Family-Friendly Cottage, Walk to the Beach!
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is SAR 368
SAR 569 total
includes taxes & fees
6 Nov 2024 - 7 Nov 2024
First Floor Studio Apartment in Historic Chestertown
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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