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Henderson Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Henderson vacation rentals

Exterior

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (25 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,728
￥19,733 total
includes taxes & fees
Aug 10 - Aug 11
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

2. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
9.8 out of 10, Exceptional, (10 reviews)
"The pictures were accurate. Our host communicated with us in a timely manner. Everything was as it said it was going to be everything in the house worked and made sense. We really enjoyed our stay. We definitely will be staying at this location again when we come in into Dover."
United States
Laura
The price is ￥17,354
￥27,601 total
includes taxes & fees
Sep 6 - Sep 7
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Interior

3. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is ￥9,229
￥15,166 total
includes taxes & fees
Aug 13 - Aug 14
Cozy Room in Dover
Property grounds

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥15,618
￥25,058 total
includes taxes & fees
Aug 10 - Aug 11
First Floor Studio Apartment in Historic Chestertown
1 bedroom, desk, iron/ironing board, WiFi

5. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (24 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is ￥8,046
￥26,551 total
includes taxes & fees
Aug 10 - Aug 11
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Pool

6. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is ￥23,664
￥38,296 total
includes taxes & fees
Sep 6 - Sep 7
Mini Aruba RV/Glamping Tent
Interior

7. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is ￥52,534
￥66,005 total
includes taxes & fees
Sep 2 - Sep 3
Family Retreat at Lansdowne Manor
TV, fireplace

8. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥28,965
￥44,394 total
includes taxes & fees
Aug 19 - Aug 20
Secluded Cottage in Middle of Chestertown
Beach

9. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,584
￥45,242 total
includes taxes & fees
Aug 10 - Aug 11
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Property grounds

10. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is ￥56,794
￥96,155 total
includes taxes & fees
Aug 10 - Aug 11
Turnbridge Manor
Dining

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (15 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is ￥39,440
￥66,054 total
includes taxes & fees
Aug 10 - Aug 11
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

12. Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Kitts Hummock
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
The price is ￥38,967
￥64,385 total
includes taxes & fees
Sep 7 - Sep 8
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Smart TV, books

13. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥35,496
￥55,554 total
includes taxes & fees
Aug 20 - Aug 21
Newly restored apartment in the heart of Chestertown
Smart TV

14. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥29,343
￥59,532 total
includes taxes & fees
Sep 2 - Sep 3
Bayside Cottage steps from Rock Hall Harbor
Property grounds

15. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥50,603
￥78,943 total
includes taxes & fees
Sep 9 - Sep 10
Wren Retweet- Country Estate in Center of C’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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"I don’t care to comment now"
Bonnie 1-night trip
Posted 7 hours ago
Comfort Inn & Suites Chestertown

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 Silver Lake 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.