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Check prices for these dates

Next weekend
25 Jul - 27 Jul
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1 Aug - 3 Aug
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15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Vacation Homes in Kennedyville

Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (163)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (177)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
Dining

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (5)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
BAYSIDE BUNGALOW
Sauna

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (42)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 735
AED 1,110 total
includes taxes & fees
21 Jul - 22 Jul
BAYSIDE BUNGALOW
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Nancy’s Touch, A Waterfront Paradise!
Property grounds

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (163)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (41)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (268)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AED 724
AED 1,655 total
includes taxes & fees
22 Jul - 23 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Property grounds

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

10.0 out of 10, Exceptional, (24)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Stay in the landmark Lighthouse!
Beach

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (101)
"Great views, unique living space and all the amenities. Really enjoyed our stay!"
Stay in the landmark Lighthouse!
Luxury 2-bedroom house with Water views, Chesapeake City
Fridge, microwave, oven, stovetop

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (1)
"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "
Luxury 2-bedroom house with Water views, Chesapeake City
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Beach nearby

Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD

10.0 out of 10, Exceptional, (19)
"We really enjoyed our stay in Rock Hall! Perfect house in a great location."
Beautiful home & short walk to beach, restaurants, and marinas in Rock Hall, MD
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (72)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Walk to Town & River: Charming Home in North East!
Fridge, microwave, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (1)
"This is our third time staying at the property. It’s under new ownership this time but the experience was just as good. We rented to stay in while at a family reunion in town. It’s perfect because it’s close to all the shops and the best coffee/donut store, Chesapeake Coffee, is right across the street! The communication with the rental service was excellent. We called to request an additional day and it was an extremely smooth process. Highly recommend this property."
Walk to Town & River: Charming Home in North East!
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (19)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Exterior

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (54)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Interior

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (53)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Marina

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

10.0 out of 10, Exceptional, (7)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall."
Anonymous traveler 2-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown