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Kennedyville Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Kennedyville holiday rentals

Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (25 reviews)
"Cleaned, beautifully decorated, not like a rental but more like a home!"
United States
Manjetjola P.
The price is HK$847
HK$2,185 total
includes taxes & fees
20 Jul - 21 Jul
Historic Chesapeake City Stay
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"We had a lovely stay at Elisabeths place. She helped us with anything we needed. The aprtment was clean, cozy and just right for 2 people."
United States
Lisa v.
The price is HK$776
HK$1,245 total
includes taxes & fees
27 Jul - 28 Jul
First Floor Studio Apartment in Historic Chestertown
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 HK$1,282
HK$1,456 total
includes taxes & fees
17 Jul - 18 Jul
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is HK$529
HK$727 total
includes taxes & fees
19 Jul - 20 Jul
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 HK$533
HK$980 total
includes taxes & fees
20 Jul - 21 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (43 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
The price is HK$549
HK$872 total
includes taxes & fees
28 Jul - 29 Jul
Country Get Away Studio Apartment
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, (49 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is HK$1,376
HK$1,666 total
includes taxes & fees
23 Jul - 24 Jul
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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)
"Kitchen was fully stocked, apartment very clean, very nice host and parking was great"
United States
Tara K.
The price is HK$923
HK$2,223 total
includes taxes & fees
17 Jul - 18 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is HK$620
HK$1,496 total
includes taxes & fees
20 Jul - 21 Jul
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
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 HK$1,524
HK$2,081 total
includes taxes & fees
21 Jul - 22 Jul
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
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 HK$1,764
HK$2,967 total
includes taxes & fees
19 Jul - 20 Jul
Waterfront Retreat with Private Dock and Beach
Interior

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
The price is HK$1,959
HK$2,330 total
includes taxes & fees
19 Jul - 20 Jul
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Interior

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (32 reviews)
"Perfect location for that town. "
United States
Hisham M.
The price is HK$1,293
HK$2,268 total
includes taxes & fees
22 Jul - 23 Jul
Private 3 room Queen Suite w/Kitchenette
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,100
HK$1,366 total
includes taxes & fees
27 Jul - 28 Jul
Turtle Cove Room
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 HK$1,481
HK$1,893 total
includes taxes & fees
17 Jul - 18 Jul
Tiny Home Tranquil Oasis
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 HK$1,721
HK$2,481 total
includes taxes & fees
19 Jul - 20 Jul
Quarry Landing - Center of Town & River View - 3 Bedroom
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 HK$1,481
HK$1,838 total
includes taxes & fees
3 Aug - 4 Aug
Nature's Haven Tiny Home
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,568
HK$2,376 total
includes taxes & fees
19 Jul - 20 Jul
BAYSIDE BUNGALOW
Property grounds

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$1,185
HK$1,466 total
includes taxes & fees
27 Jul - 28 Jul
Beachcomber Suite
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 HK$1,474
HK$2,974 total
includes taxes & fees
27 Jul - 28 Jul
Bayside Cottage steps from Rock Hall Harbor
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 Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"We stayed there two nights for my daughter’s tournament. The room is clean and quiet, the breakfast is good. Highly recommended!"
Mengna 2-night trip
Posted less than an hour ago
Comfort Inn & Suites Chestertown

Find out more about Kennedyville

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Look no further and take a look at our great range of rental properties in Kennedyville!

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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Kennedyville is located on a lake, and has a fireplace, 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 fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 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 Kent Museum and Turner Creek Park.

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.