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Compare 98 Vacation Homes in Henderson with updated reviews, rates, and availability.

Captain's Quarters

9.8 out of 10, Exceptional, (83)
"Great place to stay! The communication with the property manager was very good. The house was big enough for my husband and I, four of our adult children and some grandchildren. The bedrooms are spacious and we had enough beds and pillows for all. Our stay was in November, and we still enjoyed walking the beach, which was about a block away from the house, and watching the sunrise. The kitchen was very well equipped and everything was in working order. The only odd thing, that we got use to in...
Captain's Quarters

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

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

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

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (25)
"This is a beautiful beach house, right on the water. Lots of amenities and upgrades. We loved the screened porch and upstairs deck. We were fine with the spiral stairs but they may be potentially challenging for some guests. The area is a little isolated and the beach was quiet in mid-October, which was perfect for us! I highly recommend this property."
Wind Song Getaway on the Beach

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

10.0 out of 10, Exceptional, (5)
"Perfect rental for our family of 6 adults! Great location on the water with a fun restaurant just steps away. Highly recommend!!"
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (31)
"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"
Stylish Home on the Choptank River (with Tidal Beach)

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

10.0 out of 10, Exceptional, (18)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

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

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

9.8 out of 10, Exceptional, (24)
"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

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock

Grasonville Home w/ Private Pool on the Water

9.8 out of 10, Exceptional, (20)
"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"
Grasonville Home w/ Private Pool on the Water

Private Yard: Pet-Friendly Home in Dover

10.0 out of 10, Exceptional, (12)
"Quiet location, clean and big. "
Private Yard: Pet-Friendly Home in Dover

Cozy House, in the Historic Bowers Beach. Pet Friendly and Quiet.

10.0 out of 10, Exceptional, (3)
"A nice place to stay with everything we needed to cook an early Thanksgiving dinner for our family living from Felton. Grand kids loved the game room and the neighbors are friendly and quiet.The beach is really nice to walk off season and the full moon rising over the bay was beautiful Joseph made sure we had everything we needed and checked to make sure we were happy with the stay."
The price is AED 937
AED 1,107 total
includes taxes & fees
4 Feb - 5 Feb
Cozy House, in the Historic Bowers Beach. Pet Friendly and Quiet.

Right in the center of everywhere in Dover

8.0 out of 10, Very Good, (3)
"Everything was nice enough space for everyone to sleep comfortably."
Right in the center of everywhere in Dover

Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!

9.6 out of 10, Exceptional, (26)
"Was perfect for our needs. "
Quiet beach escape. Close to DE TURF fields.<br>TAX FREE SHOPPING!

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

10.0 out of 10, Exceptional, (9)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Beautiful new 4-bedroom house with near Killens Pond State Park and Dover AFB

Beautiful new 4-bedroom house with near Killens Pond State Park and Dover AFB

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (66)
"This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend!"
Circa 1900 Home in the Heart of Historic Downtown Chestertown
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 Henderson

Captain's Quarters

9.8 out of 10, Exceptional, (83)
"Great place to stay! The communication with the property manager was very good. The house was big enough for my husband and I, four of our adult children and some grandchildren. The bedrooms are spacious and we had enough beds and pillows for all. Our stay was in November, and we still enjoyed walking the beach, which was about a block away from the house, and watching the sunrise. The kitchen was very well equipped and everything was in working order. The only odd thing, that we got use to in...
Captain's Quarters

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

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

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.
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.