Kennedyville Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Kennedyville vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is ￥15,459
￥24,803 total
includes taxes & fees
Feb 12 - Feb 13
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, (147 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is ￥40,334
￥81,817 total
includes taxes & fees
Feb 12 - Feb 13
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is ￥10,931
￥17,380 total
includes taxes & fees
Feb 17 - Feb 18
Country Get Away 1 Bedroom Apartment
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 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is ￥18,394
￥44,615 total
includes taxes & fees
Feb 12 - Feb 13
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is ￥27,039
￥48,609 total
includes taxes & fees
Feb 24 - Feb 25
Waterfront Retreat with Private Dock and Beach
Smart TV, foosball, books

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Chesapeake City
9.4 out of 10, Exceptional, (3 reviews)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is ￥27,326
￥50,318 total
includes taxes & fees
Mar 1 - Mar 2
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,618
￥19,531 total
includes taxes & fees
Feb 12 - Feb 13
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (29 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is ￥21,861
￥38,897 total
includes taxes & fees
Mar 11 - Mar 12
Private 3 room Queen Suite w/Kitchenette
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is ￥16,864
￥42,138 total
includes taxes & fees
Feb 12 - Feb 13
Amazing Modern house with a full kitchen and parking
Pool

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
United States
Jason
The price is ￥39,209
￥65,893 total
includes taxes & fees
Feb 21 - Feb 22
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
Exterior

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, (35 reviews)
"Very cool place. "
United States
Eric L.
The price is ￥27,117
￥32,183 total
includes taxes & fees
Feb 16 - Feb 17
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Living area

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (5 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is ￥21,080
￥29,793 total
includes taxes & fees
Feb 12 - Feb 13
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Interior

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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.6 out of 10, Excellent, (14 reviews)
"Nice and quiet place to stay"
United States
Gary M.
The price is ￥20,859
￥41,764 total
includes taxes & fees
Mar 13 - Mar 14
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Yes she was welcoming "
United States
Garry B.
The price is ￥16,864
￥43,531 total
includes taxes & fees
Feb 13 - Feb 14
Historic Chesapeake City Stay
Interior

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay! "
United States
Courtney H.
The price is ￥14,639
￥43,193 total
includes taxes & fees
Feb 12 - Feb 13
Hobbit House one of a kind home
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very Good, (12 reviews)
"Pleasant stay"
United States
Yommali G.
The price is ￥10,429
￥14,330 total
includes taxes & fees
Feb 24 - Feb 25
Charming 2-bedroom house in Aberdeen with WiFi and AC
Fridge, microwave, oven, stovetop

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥22,626
￥35,238 total
includes taxes & fees
Feb 17 - Feb 18
Quarry Landing - Center of Town & River View - 3 Bedroom
Interior

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is ￥62,460
￥91,348 total
includes taxes & fees
Feb 17 - Feb 18
JVA LUXURY HOUSING
Interior

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is ￥20,300
￥62,401 total
includes taxes & fees
Mar 1 - Mar 2
Abingdon Haven Hideaway
Dining

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.8 out of 10, Excellent, (8 reviews)
"Excellent communication with host, we had everything we needed"
United States
Kelly W.
The price is ￥84,981
￥138,559 total
includes taxes & fees
Feb 24 - Feb 25
Luxury Waterfront Home Built for Entertaining!
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

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"Everything was exceptional!"
JOSEPH 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Middletown

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?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Kennedyville is located on the beach and has a fireplace, a patio, 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 and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Kennedyville?

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

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.