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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 158 Vacation Homes in Kennedyville with updated reviews, rates, and availability.

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"The house was perfect. While the weather didn't really cooperate still had time to sit on the dock and the porch watching the eagles, osprey, geese, ducks, birds and fishermen. Location near Charlestiwn and NorthEast us freat fir restaurants and shopping "
Captivating Chesapeake experience
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Fridge, microwave, oven, stovetop

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very Good, (1)
"Nice and quiet place to stay"
The price is AED 496
AED 1,043 total
includes taxes & fees
28 Apr - 29 Apr
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Terrace/patio

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (37)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (136)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,319
AED 2,398 total
includes taxes & fees
28 Apr - 29 Apr
5-bedroom vacation home 5 minutes from historic Charlestown
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Outdoor pool

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (47)
"Our stay was incredible! The house is beautiful, it is super spacious with tons of perfect places to congregate and hang out. The rooms were all extremely comfortable and the beds had high quality mattresses that made sleeping so enjoyable. The views and sunsets were spectacular and our group loved spending our evenings enjoying the hot tub. The house’s location is perfect as it is not only right on the water but it’s just under one mile from the (albeit super tiny) town of Rock Hall. I’d love...
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

9.4 out of 10, Exceptional, (15)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
The price is AED 735
AED 1,406 total
includes taxes & fees
5 May - 6 May
Tip Of The Town Fresh and New 3 Bedroom Nest
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.8 out of 10, Exceptional, (13)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Exterior

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is AED 2,071
AED 4,064 total
includes taxes & fees
28 Apr - 29 Apr
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Fridge, microwave, oven, stovetop

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Cozy 2-bedroom townhome in charming Elkton
Smart TV

Cozy 2-bedroom townhome in charming Elkton

8.0 out of 10, Very Good, (1)
"The house itself was clean. Had everything we needed. It seemed like the back yard was still being cleared of trees and debris. Was too chilly for sitting out though. All and all, was fine."
The price is AED 422
AED 526 total
includes taxes & fees
28 Apr - 29 Apr
Cozy 2-bedroom townhome in charming Elkton
Newly renovated single family home with attached guest suite
Smart TV

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Interior

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (25)
"Owner/host was absolutely the best communicator. Spectacular views. The suite was an added bonus. Great beds in all the rooms . The kitchen provided great space to prepare family meals together. Wonderful water pressure. Stayed at the home for a special getaway for mom's 91st birthday. She kept stating "I love this little house". This home surpassed our expectations. This stay will forever have special memories. We hope to return. jold special memories "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront family resort Lodge with private pier, game room and bar
Interior

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (25)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar
Nancy’s Touch, A Waterfront Paradise!
Property grounds

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (159)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!
Waterfront Oasis w/ Private Dock, 3BR/2BA
Smart TV, video games

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (33)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
Amazing Waterfront Home on the Bush River
Terrace/patio

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at Ted’s property. The basement was cold as they hadn’t figured out to adjust the thermostat yet, so we didn’t spend any time down there. We also encountered challenges with the hot water heater, but overall it was a lovely stay. "
Amazing Waterfront Home on the Bush River
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Property grounds

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Exterior

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (56)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
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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Other property types in Kennedyville

BAYSIDE BUNGALOW
Fridge, microwave, coffee/tea maker, toaster

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (34)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is AED 643
AED 993 total
includes taxes & fees
28 Apr - 29 Apr
BAYSIDE BUNGALOW
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very Good, (1)
"Nice and quiet place to stay"
The price is AED 496
AED 1,043 total
includes taxes & fees
28 Apr - 29 Apr
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Exterior

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"We all love staying on this boat and rocking to sleep! It’s nice to have the time to sit around the table and talk about the future with our granddaughters who love Bomboys Ice Cream and Candy Store the most."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.