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Henderson Vacation Rentals

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Our top choices for Henderson vacation rentals

1. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store
Hartly
The price is CA $143
CA $211 total
includes taxes & fees
Aug 29 - Aug 30
Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

2. 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, (27 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 CA $94
CA $173 total
includes taxes & fees
Sep 9 - Sep 10
Guest Suite for up to 2 in a Victorian on the Chester River

3. 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)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $137
CA $226 total
includes taxes & fees
Sep 11 - Sep 12
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

4. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is CA $81
CA $133 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Room in Dover

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $137
CA $220 total
includes taxes & fees
Sep 2 - Sep 3
First Floor Studio Apartment in Historic Chestertown

6. 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, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is CA $118
CA $286 total
includes taxes & fees
Sep 21 - Sep 22
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

7. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"We had an absolutely wonderful stay at this adorable glamping camper oasis while in town for the NASCAR All-Star Race weekend. The camper and property were spotless, beautifully maintained, and it has so many thoughtful amenities that made our stay comfortable and relaxing.The heated pool was amazing after a long day, and the entire atmosphere was peaceful, welcoming, and fun. The hosts were incredibly friendly, gracious, and accommodating throughout our stay. You can truly tell they take...
United States
Roberta J.
The price is CA $208
CA $339 total
includes taxes & fees
Sep 6 - Sep 7
Mini Aruba RV/Glamping Tent

8. 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 CA $418
CA $526 total
includes taxes & fees
Sep 2 - Sep 3
Family Retreat at Lansdowne Manor

9. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is CA $262
CA $398 total
includes taxes & fees
Sep 3 - Sep 4
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

10. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (16 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $499
CA $856 total
includes taxes & fees
Sep 1 - Sep 2
Turnbridge Manor

11. 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 CA $163
CA $396 total
includes taxes & fees
Aug 29 - Aug 30
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

12. 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 CA $254
CA $388 total
includes taxes & fees
Aug 29 - Aug 30
Secluded Cottage in Middle of Chestertown

13. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.4 out of 10, Exceptional, (11 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is CA $587
CA $1,215 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 5 Bedroom w/Pool, Patio and Theater

14. 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 CA $308
CA $518 total
includes taxes & fees
Sep 7 - Sep 8
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

15. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is CA $312
CA $488 total
includes taxes & fees
Aug 30 - Aug 31
Newly restored apartment in the heart of Chestertown

16. 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, (16 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 CA $346
CA $584 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

17. 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 CA $444
CA $690 total
includes taxes & fees
Aug 30 - Aug 31
Wren Retweet- Country Estate in Center of C’Town

18. 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 CA $270
CA $529 total
includes taxes & fees
Sep 28 - Sep 29
Bayside Cottage steps from Rock Hall Harbor
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Henderson. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Tuckahoe State Park and Killens Pond State Park.

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.