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Vacation Homes in Henderson

Captain's Quarters

9.8 out of 10, Exceptional, (99)
"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, (74)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"House was exactly as advertised. Quite community. Close to shopping, dining and beach! "
Entire Townhouse in Rock Hall

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

Delaware Turf Bungalow’s Sister!

10.0 out of 10, Exceptional, (1)
"This bungalow was the perfect getaway for the weekend. It was clean, cozy and had enough space for my children and I to relax without being on top of each other. We were close enough to several beaches and the boardwalk but far enough away to get away from the hustle and bustle of the big beach town. The host was amazing. She was so nice to communicate with and very accommodating. She made us feel very welcomed and even suggested some sights to check out around the area. The whole experience was...
Delaware Turf Bungalow’s Sister!

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

9.6 out of 10, Exceptional, (23)
"Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"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

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (40)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
Stylish Home on the Choptank River (with Tidal Beach)

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

10.0 out of 10, Exceptional, (19)
"Had everything we needed"
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

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

9.6 out of 10, Exceptional, (12)
"Nice stay, would book again. Needs new king mattress, more mirrors in the home and a water filter. Very relaxing clean, makess you want to stay in and gamg out. Close to everything cool."
The price is AED 918
AED 1,538 total
includes taxes & fees
13 Oct - 14 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

10.0 out of 10, Exceptional, (57)
"We had an awesome time at the property. The pool and jacuzzi are great for the family to play together. The house has board games and toys for the little ones, plus bikes to explore the little town. We will definitely be back. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (5)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests

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.

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.6 out of 10, Excellent, (4)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

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

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (4)
"My family had a great time during our stay! The house was very clean and nice. Views were spectacular! Katie was very responsive to all of my questions. "
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

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

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
The price is AED 724
AED 1,608 total
includes taxes & fees
6 Oct - 7 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (33)
"Location was nice, beautiful sunrises. Plenty of room, beds were super comfy and communication with owner was wondering!"
Wind Song Getaway on the Beach

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

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

10.0 out of 10, Exceptional, (26)
"Very relaxing "
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
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