Henderson Holiday Rentals

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Holiday Rentals in Henderson

Grandma's Cottage

10.0 out of 10, Exceptional, (103)
"5 nights in grandsma cottage and we enjoy every things..."
Grandma's Cottage

Captain's Quarters

9.8 out of 10, Exceptional, (94)
"This was a wonderful home walking distance to the beach. It was spacious and extremely comfortable. We recommend it to anyone interested in a beach vacation home. "
Captain's Quarters

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (227)
"Awesome place. "
Cozy cottage on the Miller farm.

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (22)
"The house was amazing, and close to Killens Pond State Park where we had additional family camping."
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
The price is AU$244
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

10.0 out of 10, Exceptional, (7)
"Perfect rental for our family of 6 adults! Great location on the water with a fun restaurant just steps away. Highly recommend!!"
Oceanview Riverfront retreat w/ hot tub and private dock! - 10 min from DE Turf

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
The price is AU$893
includes taxes & fees
27 July - 28 July
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (101)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (12)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (8)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is AU$451
includes taxes & fees
27 July - 28 July
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"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!"
The price is AU$384
includes taxes & fees
4 Aug - 5 Aug
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AU$682
includes taxes & fees
28 July - 29 July
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Peaceful living just outside of town

9.8 out of 10, Exceptional, (7)
"We really enjoyed our time there! The children enjoyed the playground set. We truly recommend! We are so grateful. Thank you! "
Peaceful living just outside of town

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (88)
"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (72)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown 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

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 Tuckahoe State Park and Killens Pond State Park.

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.