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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 158 Vacation Homes in Kennedyville with updated reviews, rates, and availability.

BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (38)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is AED 735
AED 1,078 total
includes taxes & fees
16 Jun - 17 Jun
BAYSIDE BUNGALOW
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (260)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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, (18)
"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
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (160)
"The property was great, clean and spacious. The views were remarkable and amenities exactly what we needed while we are working a major event."
Chesapeake Bay House with Dock & Private Beach
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

9.4 out of 10, Exceptional, (3)
"Nice and quiet place to stay"
The price is AED 540
AED 1,067 total
includes taxes & fees
16 Jun - 17 Jun
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Cozy 2-bedroom townhome in charming Elkton
Fridge, microwave, oven, stovetop

Cozy 2-bedroom townhome in charming Elkton

8.8 out of 10, Excellent, (3)
"This home wss a perfect stay for me and my friends, spacious, clean, and as described "
The price is AED 422
AED 526 total
includes taxes & fees
22 Jun - 23 Jun
Cozy 2-bedroom townhome in charming Elkton
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (14)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun loungers, beach towels

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (97)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Fridge, microwave, oven, stovetop

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (12)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
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, (39)
"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
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, (47)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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)
"The place is well cared and cute. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Beautiful, spacious, quiet waterfront house!
Fridge, microwave, oven, stovetop

Beautiful, spacious, quiet waterfront house!

10.0 out of 10, Exceptional, (48)
"Wonderful stay – Kids enjoyed fishing, floating in tubes and the hot tub! Very clean property with comfortable beds."
Beautiful, spacious, quiet waterfront house!
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, (20)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Chesapeake City Quiet Overlook
Outdoor dining

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (18)
"Everyone in our family ages 8, 10, 17, 18, 38, 64, and 71 thought the house and location were perfect and we had a great stay."
Chesapeake City Quiet Overlook
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (77)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Fridge, microwave, oven, stovetop

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Waterfront Oasis w/ Private Dock, 3BR/2BA
Marina

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (33)
"Quick stay so I could visit family in Abingdon and DC. So awesome. Beautiful property even with the raging wind and snow storm."
Waterfront Oasis w/ Private Dock, 3BR/2BA
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,319
AED 2,398 total
includes taxes & fees
4 Jun - 5 Jun
5-bedroom vacation home 5 minutes from historic Charlestown
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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