Henderson Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Henderson

Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Millington

9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,576
￥19,454 total
includes taxes & fees
Nov 20 - Nov 21
Guest Suite for up to 2 in a Victorian on the Chester River
Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Apartment in Rock Hall

10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is ￥18,321
￥44,273 total
includes taxes & fees
Nov 20 - Nov 21
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,372
￥24,663 total
includes taxes & fees
Nov 20 - Nov 21
First Floor Studio Apartment in Historic Chestertown
Dining
Amazing Modern house with a full kitchen and parking

Vacation Home in Smyrna

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is ￥27,995
￥55,539 total
includes taxes & fees
Nov 20 - Nov 21
Amazing Modern house with a full kitchen and parking
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Grasonville

9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is ￥38,883
￥65,121 total
includes taxes & fees
Nov 20 - Nov 21
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in Centreville

10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is ￥30,655
￥69,259 total
includes taxes & fees
Dec 1 - Dec 2
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Property grounds
Turnbridge Manor

Vacation Home in Denton

9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥55,897
￥93,485 total
includes taxes & fees
Dec 1 - Dec 2
Turnbridge Manor
Interior
Spacious 5 Bedroom w/Pool, Patio and Theater

Vacation Home in Magnolia

9.8 out of 10, Exceptional, (7)
"Great house for a large family "
United States
Stephanie
The price is ￥41,422
￥107,364 total
includes taxes & fees
Nov 23 - Nov 24
Spacious 5 Bedroom w/Pool, Patio and Theater
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Vacation Home in Rock Hall

2.5 star property
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is ￥34,994
￥42,369 total
includes taxes & fees
Nov 20 - Nov 21
Chesapeake Bay Harbor View in a central location to events/restaurants
Private kitchen
JVA LUXURY HOUSING

Vacation Home in Smyrna

10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is ￥62,108
￥91,454 total
includes taxes & fees
Nov 25 - Nov 26
JVA LUXURY HOUSING
Marina
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (2)
"I spent a wonderful 8 nights at the Dragonfly Cottage in the quaint bayside town of Rock Hall. The cottage was in a prime location and perfectly situated for long morning walks around the town. The cottage itself is brand new with every accommodation you can think of to have a comfortable stay. The 3 large bedrooms and open floor plan kitchen / living area provide plenty of space to spread out. Everything was sparkling clean and you can tell the hosts have taken a lot of care to anticipate your...
United States
Alison F.
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall
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

Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

10/10 Excellent
"Parking was good. Room was fine Breakfast could have been a little better with more protein options. Overall good stay"
William 1-night trip
Posted 2 days ago
Red Roof Inn & Suites Dover Downtown

Find out more about Henderson

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Frequently asked questions

Are there vacation rentals in Henderson?

Yes, you can find vacation rentals close to the most popular local attractions in Henderson, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Henderson has to offer?

Cozy cottage on the Miller farm. : This vacation home rental near Henderson offers a private yard, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Henderson?

While exploring the area, visit family-friendly sights like Delaware State Fairgrounds, or get outside and enjoy nature at Saulsbury Road Park. In the larger area, you’ll find Killens Pond State Park and Air Mobility Command Museum.

What’s a vacation rental in Henderson like?

A vacation rental is a private property where you can stay for short or long periods in Henderson. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family getaway.