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Henderson Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Henderson holiday 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, (28 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 HK$533
HK$890 total
includes taxes & fees
29 Sept - 30 Sept
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
9.8 out of 10, Exceptional, (10 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is HK$706
HK$1,208 total
includes taxes & fees
30 Sept - 1 Oct
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

3. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is HK$1,255
HK$2,025 total
includes taxes & fees
30 Sept - 1 Oct
Mini Aruba RV/Glamping Tent
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is HK$776
HK$1,246 total
includes taxes & fees
29 Sept - 30 Sept
First Floor Studio Apartment in Historic Chestertown
A bedroom with a bunk bed, a single bed, a desk, and a chair.

5. 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 HK$549
HK$1,436 total
includes taxes & fees
13 Oct - 14 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A kitchen with wooden cabinets, a dining table, and a refrigerator.

6. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 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 HK$2,635
HK$3,283 total
includes taxes & fees
30 Sept - 1 Oct
Family Retreat at Lansdowne Manor
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

7. 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.
The price is HK$1,874
HK$4,288 total
includes taxes & fees
29 Sept - 30 Sept
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
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.

8. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$2,823
HK$4,813 total
includes taxes & fees
7 Oct - 8 Oct
Turnbridge Manor
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

9. 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.
The price is HK$1,725
HK$2,452 total
includes taxes & fees
22 Oct - 23 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

10. 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 HK$1,440
HK$2,149 total
includes taxes & fees
8 Oct - 9 Oct
Secluded Cottage in Middle of Chestertown
A garden with a variety of plants and a small bridge.

11. 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 HK$2,389
HK$3,775 total
includes taxes & fees
6 Oct - 7 Oct
Wren Retweet- Country Estate in Center of C’Town
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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)
The price is HK$973
HK$2,303 total
includes taxes & fees
27 Sept - 28 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A deck with a table and chairs, a large umbrella, and a grill.

13. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
The price is HK$3,294
HK$5,740 total
includes taxes & fees
30 Sept - 1 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat
A round window with a view of a garden, a tree, and a building in the background.

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 HK$1,762
HK$2,978 total
includes taxes & fees
11 Oct - 12 Oct
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

15. 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 HK$2,157
HK$3,983 total
includes taxes & fees
25 Sept - 26 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A bedroom with a bed, a ceiling fan, a large mirror, and a door.

16. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
The price is HK$2,753
HK$5,678 total
includes taxes & fees
4 Oct - 5 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

17. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is HK$1,600
HK$3,126 total
includes taxes & fees
28 Sept - 29 Sept
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

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."
John 2-night trip
Posted 14 hours ago
Red Roof Inn & Suites Chestertown

Find out more about Henderson

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Look no further and take a look at our great range of rental properties in Henderson!

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?

Captain's Quarters: This holiday home rental outside of Henderson is located near the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.