Henderson Vacation Rentals

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Browse Select Henderson Vacation Homes

Our top choices for Henderson vacation homes

Captain's Quarters

9.8 out of 10, Exceptional, (97)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (18)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (30)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (25)
"Nice stay… good family home…. Lots of sleeping accommodations…. A few steps from the beach!!!!! Great host!!!!!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (231)
"Awesome place. "
Cozy cottage on the Miller farm.

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Enjoyed this lovely and comfortable home tucked away in a private location close to amenities. "
Peaceful Queenstown Home w/ Deck & Grill!

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

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

9.6 out of 10, Exceptional, (21)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (22)
"I needed a place for four adults and three children to stay while I hosted a family reunion near nearby. This rental is clean, comfortable, with upgrades throughout. Plenty of bathrooms, a large kitchen and in a nice residential area. I would highly recommend to a family with a few children."
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (23)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $344
CA $567 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Waterfront Estate w Private Pier, Game Room & Bar

9.8 out of 10, Exceptional, (31)
"We take a family vacation every year and this was so perfect! Great for the kids. "
Waterfront Estate w Private Pier, Game Room & Bar

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

10.0 out of 10, Exceptional, (81)
"Loved our stay!"
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (89)
"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

10.0 out of 10, Exceptional, (11)
"We loved our stay! "
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (5)
"My Cousin lives in the neighborhood and was having a Calibration of Life at her house for her deceased Parents. One passed in 2020, and the other just passed in October of last year. Many relatives came for the Calibration. I rented the house to have a sleep for a Sister and her husband and my cousin. they came from Connecticut, and New Yark State. Me and my spouse came up from Georgia. The house was immaculate, practical and suited us to a T. We were 1.2 miles from the Celebration and couldn't...
RELAX- Eastern Shore Creek Home - 6 Guests

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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 Henderson Hotel Reviews

Find out more about Henderson

Find out more about Henderson

Henderson Vacation Homes information

Number of reviews
Accommodation
135 Vacation Homes
Lowest Price
CA $344
Highest Price
CA $344

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