Default HTG hotel image

Henderson Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Henderson vacation rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$118 nightly
The price is $125
Oct 28 - Oct 29
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$181 nightly
The price is $186
Oct 31 - Nov 1
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Oct 26 - Oct 27
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A bedroom with a bunk bed, a single bed, a desk, and a chair.

4. 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.
$181 nightly
The price is $184
Oct 25 - Oct 26
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A garden path leading to a wooden building with a rustic appearance.

5. 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.
$264 nightly
The price is $274
Oct 25 - Oct 26
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

6. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Host was great"
United States
mark o.
$608 nightly
The price is $619
Nov 2 - Nov 3
Total with taxes and fees
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
$269 nightly
The price is $285
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A spacious living area with a dining table, sofa, and a kitchen in the background.

8. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
$320 nightly
The price is $353
Oct 26 - Oct 27
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
A modern kitchen with a large island, bar stools, and pendant lighting.

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

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
$667 nightly
The price is $679
Oct 25 - Oct 26
Total with taxes and fees
Spacious 5 Bedroom w/Pool, Patio and Theater
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

10. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
$575 nightly
The price is $610
Oct 27 - Oct 28
Total with taxes and fees
Turnbridge Manor
A room with a bed, a hammock, a window with curtains, a small table, and a basket.

11. 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.
$375 nightly
The price is $385
Oct 25 - Oct 26
Total with taxes and fees
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
A house with a blue front door, two windows, and a small porch.

12. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$257 nightly
The price is $284
Oct 25 - Oct 26
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A bedroom with a large bed, wooden bookshelves, a tall black column, and large windows.

13. 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.
$470 nightly
The price is $489
Nov 3 - Nov 4
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
A dining area with a round table, chairs, a chandelier, and patterned wallpaper.

14. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
$732 nightly
The price is $732
Oct 25 - Oct 26
Total with taxes and fees
Walk to Bowers Beach! Peaceful Coastal Retreat
A dining area with a round table, chairs, a chandelier, and patterned wallpaper.

15. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
$711 nightly
The price is $728
Oct 25 - Oct 26
Total with taxes and fees
Walk to Bowers Beach! Peaceful Coastal Retreat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Henderson Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Nice staff Helpful"
carol 1-night trip
Posted 17 hours ago
Comfort Inn & Suites Chestertown

Find out more about Henderson

Everything you need to know about Henderson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Henderson vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Henderson vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Henderson vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Henderson. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Henderson in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Henderson rentals

At Expedia, we put the best Henderson vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Henderson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Henderson vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Henderson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Captain's Quarters: This vacation home rental near Henderson is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.