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Kennedyville Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Kennedyville holiday rentals

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is HK$776
HK$1,245 total
includes taxes & fees
2 Sept - 3 Sept
First Floor Studio Apartment in Historic Chestertown
Exterior

2. 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, (27 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 HK$533
HK$981 total
includes taxes & fees
10 Sept - 11 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

3. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is HK$1,251
HK$1,554 total
includes taxes & fees
31 Aug - 1 Sept
Beachcomber Suite
Room

4. Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,101
HK$1,366 total
includes taxes & fees
31 Aug - 1 Sept
Turtle Cove Room
Living area

5. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is HK$1,439
HK$2,215 total
includes taxes & fees
1 Sept - 2 Sept
Secluded Cottage in Middle of Chestertown
Beach

6. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is HK$1,764
HK$2,952 total
includes taxes & fees
31 Aug - 1 Sept
Waterfront Retreat with Private Dock and Beach
Living area

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is HK$1,482
HK$2,269 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Marina

8. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is HK$847
HK$2,219 total
includes taxes & fees
31 Aug - 1 Sept
Historic Chesapeake City Stay
Exterior

9. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is HK$549
HK$873 total
includes taxes & fees
9 Sept - 10 Sept
Country Get Away Studio Apartment
Terrace/patio

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (6 reviews)
The price is HK$1,215
HK$1,479 total
includes taxes & fees
31 Aug - 1 Sept
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Living area

11. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is HK$670
HK$877 total
includes taxes & fees
6 Sept - 7 Sept
Charming 2-bedroom house in Aberdeen with WiFi and AC
Beach

12. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is HK$924
HK$2,257 total
includes taxes & fees
31 Aug - 1 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Living area

13. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is HK$1,764
HK$2,761 total
includes taxes & fees
31 Aug - 1 Sept
Newly restored apartment in the heart of Chestertown
Exterior

14. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store
Hartly
The price is HK$808
HK$1,197 total
includes taxes & fees
31 Aug - 1 Sept
Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store
Property grounds

15. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is HK$2,515
HK$3,923 total
includes taxes & fees
1 Sept - 2 Sept
Wren Retweet- Country Estate in Center of C’Town
Exterior

16. 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, (51 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is HK$1,376
HK$1,666 total
includes taxes & fees
31 Aug - 1 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

17. 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, (2 reviews)
"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 HK$1,294
HK$1,493 total
includes taxes & fees
31 Aug - 1 Sept
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Interior

18. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"The Port Deposit area is a favorite "mini-vacation" location with great bars/restaurants and beautiful walks. We've stayed at this property a number of times and we've found the rooms to be perfect for our needs. "
United States
Lance W.
The price is HK$1,294
HK$2,285 total
includes taxes & fees
1 Sept - 2 Sept
Private 3 room Queen Suite w/Kitchenette
Exterior detail

19. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is HK$1,568
HK$2,475 total
includes taxes & fees
31 Aug - 1 Sept
BAYSIDE BUNGALOW
Exterior

20. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,851
HK$3,022 total
includes taxes & fees
13 Sept - 14 Sept
Bohemia Manor Farm
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

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

10/10 Excellent
"A great variety of water slides for the kids to enjoy. The restaurant and hotel accommodations are also nice. My 2 granddaughters had a lot of fun."
john 2-night trip
Posted 1 day ago
Great Wolf Lodge Perryville

Find out more about Kennedyville

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Frequently asked questions

Can I find a holiday rental in Kennedyville?

Yes, there are holiday rentals close to the most popular sights in Kennedyville, or you can select a more secluded option if you're looking for a relaxing stay.

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

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Kennedyville is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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 Crow Farm and Vineyard and Kent Museum.

What’s a holiday rental in Kennedyville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kennedyville. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family trips or small group gatherings.