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, (108 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
Mar 16 - Mar 17
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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, (17 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
$185 nightly
The price is $188
Mar 16 - Mar 17
Total with taxes and fees
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Captain's Quarters

Captain's Quarters
Frederica
9.8 out of 10, Exceptional, (109 reviews)
"The house was perfect for our family weekend together, very clean and comfortable."
United States
Christine D.
$447 nightly
The price is $457
Mar 15 - Mar 16
Total with taxes and fees
Captain's Quarters

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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$259 nightly
The price is $286
Mar 15 - Mar 16
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Mar 24 - Mar 25
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

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, (12 reviews)
"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.
$397 nightly
The price is $421
Mar 16 - Mar 17
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
$292 nightly
The price is $298
Mar 22 - Mar 23
Total with taxes and fees
Amazing Modern house with a full kitchen and parking

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.
$557 nightly
The price is $590
Mar 16 - Mar 17
Total with taxes and fees
Turnbridge Manor

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.
$341 nightly
The price is $361
Apr 1 - Apr 2
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor

Stillwater at Kennersley

Stillwater at Kennersley
Church Hill
$832 nightly
The price is $979
Mar 17 - Mar 18
Total with taxes and fees
Stillwater at Kennersley

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
$571 nightly
The price is $589
Mar 21 - Mar 22
Total with taxes and fees
JVA LUXURY HOUSING
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 $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?

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac: This vacation home rental near Henderson is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, 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 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.