Default HTG hotel image

Kennedyville Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Kennedyville vacation rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (23 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is AED 397
AED 1,024 total
includes taxes & fees
1 Jul - 2 Jul
Historic Chesapeake City Stay
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (42 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is AED 257
AED 409 total
includes taxes & fees
7 Jul - 8 Jul
Country Get Away Studio Apartment
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
The price is AED 248
AED 341 total
includes taxes & fees
6 Jul - 7 Jul
Charming 2-bedroom house in Aberdeen with WiFi and AC
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (114 reviews)
"Every thing was great"
United States
lesia k.
The price is AED 364
AED 583 total
includes taxes & fees
6 Jul - 7 Jul
First Floor Studio Apartment in Historic Chestertown
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
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is AED 250
AED 459 total
includes taxes & fees
6 Jul - 7 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
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, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is AED 455
AED 1,071 total
includes taxes & fees
6 Jul - 7 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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
9.8 out of 10, Exceptional, (47 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AED 645
AED 773 total
includes taxes & fees
1 Jul - 2 Jul
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (1 review)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is AED 601
AED 682 total
includes taxes & fees
1 Jul - 2 Jul
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Property grounds

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is AED 281
AED 629 total
includes taxes & fees
8 Jul - 9 Jul
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is AED 606
AED 1,055 total
includes taxes & fees
6 Jul - 7 Jul
Private 3 room Queen Suite w/Kitchenette
Smart TV

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, (12 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
The price is AED 698
AED 946 total
includes taxes & fees
13 Jul - 14 Jul
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Interior

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
The price is AED 825
AED 1,466 total
includes taxes & fees
1 Jul - 2 Jul
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Terrace/patio

Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is AED 694
AED 858 total
includes taxes & fees
1 Jul - 2 Jul
Nature's Haven Tiny Home
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AED 826
AED 1,391 total
includes taxes & fees
8 Jul - 9 Jul
Waterfront Retreat with Private Dock and Beach
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, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AED 750
AED 1,107 total
includes taxes & fees
7 Jul - 8 Jul
Quarry Landing - Center of Town & River View - 3 Bedroom
Terrace/patio

Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (1 review)
"This unit is located behind a mansion /b&b. Had what we needed, clean, easy to access and Karin was helpful."
United States
Megan M.
The price is AED 694
AED 876 total
includes taxes & fees
1 Jul - 2 Jul
Tiny Home Tranquil Oasis
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is AED 779
AED 1,499 total
includes taxes & fees
28 Jul - 29 Jul
Bayside Cottage steps from Rock Hall Harbor
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (56 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,114 total
includes taxes & fees
8 Jul - 9 Jul
BAYSIDE BUNGALOW
Terrace/patio

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (1 review)
"Booked this property as a last minute, overnight getaway for myself and it was fantastic! The apartment, grounds and hot tub was squeaky clean. Kitchen was clean and stocked with utensils and even had a coffee bar, different tea packets and a snack basket. Bathroom was fully stocked with towels, basic toiletries and everything I needed. Bed was comfortable and closets had extra blankets if needed. Inside and outside patio furniture was comfy. I loved watching the sunset from the hot tub! Also...
United States
Kayla K.
The price is AED 575
AED 688 total
includes taxes & fees
6 Jul - 7 Jul
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
TV, fireplace

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (6 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
Long Beach Cottage, (romantic couple’s getaway)
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kennedyville Hotel Reviews

Wingate by Wyndham North East

Wingate by Wyndham North East

10/10 Excellent
"A little hard to find, but well worth it. An obvious recent renovation makes for a welcome that is only beat out by meeting Candy at the front desk. She was extremely pleasant to work with and is a great ambassador to the Wyndham brand. The rooms were VERY clean.... Just like the rest of the facility. Breakfast was spot on and plentiful. I would highly recommend this for your future stay in the area. The only other comment I can make is that parking is tight due to the plethora of AMTRAK vehicles in the parking lot. They have a contract for lodging there and their large trucks take a lot of space. Other than that... Go, See, Do. You'll be glad you did"
Steven 3-night trip
Posted 1 day ago
Wingate by Wyndham North East

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.