Kennedyville Vacation Rentals

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Check prices for these dates

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Nov 22 - Nov 23
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Nov 23 - Nov 24
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Vacation Rentals in Kennedyville

Exterior
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville
10.0 out of 10, Exceptional, (20)
"The property was beautiful. The views from both the house and the backyard were incredible. We can’t wait to come back and stay here in the warmer month."
United States
Todd C.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront
Interior
Charming 2-bedroom cabin close to Fair Hill on horse farm

Charming 2-bedroom cabin close to Fair Hill on horse farm

Elkton
9.6 out of 10, Exceptional, (13)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Outdoor dining
Chesapeake Bay House with Dock & Private Beach

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (177)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,485
￥24,845 total
includes taxes & fees
Nov 25 - Nov 26
First Floor Studio Apartment in Historic Chestertown
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is ￥50,536
￥94,023 total
includes taxes & fees
Nov 24 - Nov 25
5-bedroom vacation home 5 minutes from historic Charlestown
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.0 out of 10, Very Good, (5)
The price is ￥77,423
￥129,983 total
includes taxes & fees
Nov 24 - Nov 25
Luxury Waterfront Home Built for Entertaining!
Private kitchen
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown
10.0 out of 10, Exceptional, (2)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Interior
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

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

Perryville
9.2 out of 10, Wonderful, (181)
"An amazing time and great family memories it simply was a delight and was very relaxing. So many things around to do. Definitely would stay again. "
United States
Stacey W.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥28,154
￥43,107 total
includes taxes & fees
Nov 23 - Nov 24
BAYSIDE BUNGALOW
Smart TV, books
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Property grounds
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Fridge, microwave, oven, stovetop
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Havre de Grace
9.8 out of 10, Exceptional, (6)
"Beautiful home and property. The house was clean and welcoming and the pool was an absolute delight. Would definitely stay again! "
United States
Julia B.
The price is ￥126,692
￥210,227 total
includes taxes & fees
Nov 24 - Nov 25
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

Port Deposit
10.0 out of 10, Exceptional, (30)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is ￥27,450
￥32,744 total
includes taxes & fees
Nov 24 - Nov 25
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Marina
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

Middle River
9.4 out of 10, Exceptional, (38)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
United States
Vince E.
Waterfront Oasis w/ Private Dock, 3BR/2BA
Beach
Captivating Chesapeake experience

Captivating Chesapeake experience

Perryville
10.0 out of 10, Exceptional, (279)
"Nothing more beautiful than staying by the water at Joe’s place!Such a wonderful place to unwind and refuel!"
United States
Doreen H.
Captivating Chesapeake experience
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is ￥18,425
￥44,524 total
includes taxes & fees
Nov 24 - Nov 25
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Fridge, microwave, oven, stovetop
Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis

Bear
The price is ￥29,561
￥37,774 total
includes taxes & fees
Nov 23 - Nov 24
Tiny Home Tranquil Oasis
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (18)
"The property was clean and simply appointed w just the bare essentials for a short stay. Location was convenient for our purposes and the host was communicative"
United States
Melvin P.
The price is ￥16,892
￥43,604 total
includes taxes & fees
Nov 23 - Nov 24
Historic Chesapeake City Stay
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

Elkton
8.0 out of 10, Very Good, (9)
"Nice and quiet place to stay"
United States
Gary M.
The price is ￥21,115
￥43,935 total
includes taxes & fees
Nov 24 - Nov 25
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (43)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
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 North East

Comfort Inn & Suites North East

10/10 Excellent
"Very nice for the price!"
Sebastian 3-night trip
Posted 3 days ago
Comfort Inn & Suites North East

Find out more about Kennedyville

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Frequently asked questions

Can I find a vacation rental in Kennedyville?

Yes, there are vacation rentals close to top local attractions in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Kennedyville has to offer?

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This vacation home rental near Kennedyville is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

What’s there to see and do in Kennedyville?

Turner Creek Landing Park and Turner's Creek Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Crow Farm and Vineyard and Kent Museum.

What’s a vacation rental in Kennedyville like?

Vacation rentals are private properties where you can stay for a long or short time in Kennedyville. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.