Henderson Vacation Rentals

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Our top choices for Henderson vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
Jun 8 - Jun 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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
9.6 out of 10, Exceptional, (24 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.
$118 nightly
The price is $125
Jun 3 - Jun 4
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
10.0 out of 10, Exceptional, (21 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
$170 nightly
The price is $172
Jun 2 - Jun 3
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

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, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$255 nightly
The price is $281
Jun 2 - Jun 3
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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, (2 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
$148 nightly
The price is $152
Jun 23 - Jun 24
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (5 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.
$230 nightly
The price is $236
Jun 16 - Jun 17
Total with taxes and fees
Mini Aruba RV/Glamping Tent

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, (13 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
$398 nightly
The price is $422
Jun 2 - Jun 3
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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
Dover
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.
$418 nightly
The price is $430
Jun 21 - Jun 22
Total with taxes and fees
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
$343 nightly
The price is $364
Jun 2 - Jun 3
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor

Cozy home in Milford/Harrington for relaxing stays!

Cozy home in Milford/Harrington for relaxing stays!
Harrington
$222 nightly
The price is $231
Jun 2 - Jun 3
Total with taxes and fees
Cozy home in Milford/Harrington for relaxing stays!

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
8.8 out of 10, Excellent, (5 reviews)
"Destination wedding location. Family, fun, and fellowship in this comfortable home with all the amenities! We played pool, enjoyed the central location, and used all the beds. Check in was easy and host was supportive. It met our needs and we felt right at home. "
United States
Linda K.
$468 nightly
The price is $478
Jun 2 - Jun 3
Total with taxes and fees
Right in the center of everywhere in Dover

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Jun 8 - Jun 9
Total with taxes and fees
Turnbridge Manor

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$346 nightly
The price is $382
Jun 3 - Jun 4
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
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

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 $125 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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This vacation home rental near Henderson is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.