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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 127 Vacation Homes in Henderson with updated reviews, rates, and availability.

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

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

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

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Interior

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

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

10.0 out of 10, Exceptional, (85)
"Gorgeous views and surroundings"
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
SOBO Beach House
Property grounds

SOBO Beach House

9.6 out of 10, Exceptional, (12)
"We had a great stay for a lacrosse tournament we were in town for and would stay again in the future. The house had everything we needed for our stay. Sierra was great to work with. The only down side to the stay was that we did not feel the beach/bay was swimmable, but still enjoyed our walks on the beach and searching for shells."
SOBO Beach House
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, (12)
"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Beach

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
15 Apr - 16 Apr
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Stylish Home on the Choptank River (with Tidal Beach)
Property grounds

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (32)
"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."
Stylish Home on the Choptank River (with Tidal Beach)
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
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.
Fridge, microwave, oven, stovetop

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.
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
Game room

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
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
Smart TV, books

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
Gorgeous Creek Side Ranch-Style Estate With Dock
Fridge, microwave, oven, stovetop

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
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Terrace/patio

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
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!
Peaceful South Bowers Beach Pink Firehouse near DE Turf with amazing views
Beach

Peaceful South Bowers Beach Pink Firehouse near DE Turf with amazing views

10.0 out of 10, Exceptional, (5)
"We had a wonderful time at the firehouse. The property was a great peaceful place to stay. The host has great communication and was super easy to work with. If we come back to this area we would definitely stay at the firehouse again. "
Peaceful South Bowers Beach Pink Firehouse near DE Turf with amazing views
Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
Fridge, microwave, oven, stovetop

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Beach nearby, sun loungers, beach towels

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
Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (85)
"We played the DE Turf and stayed in this house instead of the very pricey and not great hotel options. Solid house. Clean. Cool little town. Bring all your food etc, this is the middle of nowhere, but it is super convenient to the fields and right by a bay beach. Sean, the owner, was very responsive. "
Captain's Quarters
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

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (81)
"The space was very clean. Communication with the owner was a breeze. It was quiet. The neighborhood is great. It is close to downtown Chestertown. A fabulous stay! "
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (34)
"Wonderful stay for 75th and 50th birthday celebrations.Everyone from age 4 to 75 had a terrific time. So much to do we did not leave the property. View of the Chesapeake Bay is amazing - from sunrise to gorgeous sunsets. Plenty of room for everyone. Great communication from host with instructions and area suggestions. 5 Star"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
Smart TV, books

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
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.