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Henderson Holiday Rentals

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Our top choices for Henderson holiday rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (116 reviews)
"Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!"
United States
Rob C.
The price is NZ$278
includes taxes & fees
13 July - 14 July
First Floor Studio Apartment in Historic Chestertown

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 NZ$530
includes taxes & fees
14 July - 15 July
Mini Aruba RV/Glamping Tent

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, (23 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 NZ$219
includes taxes & fees
15 July - 16 July
Guest Suite for up to 2 in a Victorian on the Chester River

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is NZ$667
includes taxes & fees
9 July - 10 July
Newly restored apartment in the heart of Chestertown

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)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is NZ$957
includes taxes & fees
8 July - 9 July
Wren Retweet- Country Estate in Center of C’Town

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, (6 reviews)
The price is NZ$325
includes taxes & fees
14 July - 15 July
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (13 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,061
includes taxes & fees
8 July - 9 July
Turnbridge Manor

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 NZ$698
includes taxes & fees
8 July - 9 July
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

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, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is NZ$501
includes taxes & fees
8 July - 9 July
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Right in the center of everywhere in Dover

Right in the center of everywhere in Dover
Dover
9.2 out of 10, Wonderful, (7 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.
The price is NZ$733
includes taxes & fees
3 Aug - 4 Aug
Right in the center of everywhere in Dover

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.
The price is NZ$321
includes taxes & fees
8 July - 9 July
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

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 NZ$640
includes taxes & fees
14 July - 15 July
Bayside Cottage steps from Rock Hall Harbor

Cozy Room in Dover

Cozy Room in Dover
Dover
The price is NZ$168
includes taxes & fees
11 July - 12 July
Cozy Room in Dover
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Henderson holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Henderson. 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 Henderson. 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 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 holiday 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 Henderson short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Henderson?

Yes, there are holiday rentals close to the most popular sights in Henderson, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Henderson has to offer?

Cozy 3BR/2Bath Retreat on Half Acre Near Dover Attractions DE Turf: This holiday home rental outside of Henderson offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 wider area, you’ll find Killens Pond State Park and Air Mobility Command Museum.

What’s a holiday rental in Henderson like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Henderson. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.