Search Vacation Homes in Kennedyville

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Kennedyville vacation homes

Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.8 out of 10, Exceptional, (8)
"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 AED 661
AED 1,289 total
includes taxes & fees
14 Dec - 15 Dec
Amazing Modern house with a full kitchen and parking
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Small House on Gentleman’s Farm

Small House on Gentleman’s Farm
Bel Air
10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
The price is AED 422
AED 1,121 total
includes taxes & fees
18 Dec - 19 Dec
Small House on Gentleman’s Farm
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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.0 out of 10, Very Good, (11)
"Nice and quiet place to stay"
United States
Gary M.
The price is AED 496
AED 1,043 total
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Property grounds
Hobbit House one of a kind home

Hobbit House one of a kind home

Hobbit House one of a kind home
Bel Air
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
The price is AED 436
AED 1,104 total
includes taxes & fees
13 Jan - 14 January 2026
Hobbit House one of a kind home
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

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is AED 250
AED 775 total
includes taxes & fees
14 Dec - 15 Dec
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is AED 724
AED 1,612 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is AED 636
AED 733 total
includes taxes & fees
14 Dec - 15 Dec
High Tide Haven Suite
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AED 826
AED 1,001 total
includes taxes & fees
14 Dec - 15 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Bel Air
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
A heated pool
Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
2.0 star property
Middletown
The price is AED 481
AED 1,718 total
includes taxes & fees
12 Jan - 13 January 2026
Heated Pool • Private Backyard • Home Theater
Outdoor dining
BAYSIDE BUNGALOW

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 AED 735
AED 1,110 total
includes taxes & fees
1 Jan - 2 January 2026
BAYSIDE BUNGALOW
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

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 AED 1,187
AED 2,223 total
includes taxes & fees
15 Dec - 16 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
Private kitchen
JVA LUXURY HOUSING

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is AED 1,469
AED 2,163 total
includes taxes & fees
20 Dec - 21 Dec
JVA LUXURY HOUSING
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.6 out of 10, Excellent, (7)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is AED 1,818
AED 3,052 total
includes taxes & fees
14 Dec - 15 Dec
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Everything was well!"
Ahmed 1-night trip
Posted 1 day ago
Comfort Inn & Suites Chestertown