Vacation rentals in Kennedyville

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Top-rated vacation rentals in Kennedyville

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Farm stay in Chestertown

4.94 out of 5 average rating, 106 reviews

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Apr 12 – 19

R4,408 ZAR per night
Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 107 reviews

Scenic, private 2 room-guest suite, near Bel Air

Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Feb 2 – 9

R1,936 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 150 reviews

Historic house, near town center, pet friendly

Renovated 19th century home with all modern conveniences. First floor bedroom with private bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from both Washington College and the C'town waterfront. 2 primary bedroom suites (one on the second floor has a king bed) 2 more bedrooms with queen beds. 1 loft which is connected to the a 2nd story bedroom has 2 twins. Fenced yard and over an acre of totally private gardens. Fire pit.

Dec 10 – 17

R6,629 ZAR per night

Popular amenities for Kennedyville vacation rentals

Other great vacation rentals in Kennedyville

Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Apr 4 – 11

R5,839 ZAR per night
Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 202 reviews

Eastern Shore Charm on Winchester Creek

Aug 21 – 28

R2,511 ZAR per night
Guest favorite

Home in Kennedyville

4.89 out of 5 average rating, 71 reviews

Perfect for Hunters on the Eastern Shore

Apr 10 – 17

R3,320 ZAR per night
Superhost

Cottage in Betterton

4.8 out of 5 average rating, 51 reviews

Cottage By the Chesapeake

May 13 – 20

R2,347 ZAR per night
Guest favorite

Home in Betterton

5.0 out of 5 average rating, 17 reviews

Ruby's Sea Glass Cottage near Betterton Beach

Jun 25 – Jul 2

R4,160 ZAR per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Feb 3 – 10

R3,037 ZAR per night
Guest favorite

Apartment in Worton

5.0 out of 5 average rating, 16 reviews

Historic Country Living Near Chesapeake Bay

Jul 14 – 21

R3,556 ZAR per night
Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

Nov 26 – Dec 3

R2,585 ZAR per night
Guest favorite

Home in Galena

4.89 out of 5 average rating, 70 reviews

Yellow Door Cottage

Jun 22 – 29

R3,684 ZAR per night
Guest favorite

Cottage in Earleville

4.94 out of 5 average rating, 35 reviews

The Cottage at Crystal

Apr 27 – May 4

R2,956 ZAR per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

R9,785 ZAR per night
Guest favorite

Condo in Betterton

4.93 out of 5 average rating, 30 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

May 15 – 22

R6,886 ZAR per night

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