Holiday Rentals in Henderson

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Holiday Rentals in Henderson

Pool
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (51)
"Beautiful and huge property. Paddling in the river was great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Exterior
Grandma's Cottage
10.0 out of 10, Exceptional, (77)
"Great place to relax and unwind. Our second time staying and we will be back. Wonderful proprietor"
Grandma's Cottage
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Private kitchen
Retreat Near Dover
10.0 out of 10, Exceptional, (1)
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is €432
includes taxes & fees
3 Jun - 4 Jun
Retreat Near Dover
Property grounds
Wind Song Getaway on the Beach
10.0 out of 10, Exceptional, (13)
"The house is clean and has everything you might need. The views are spectacular. The screened in porch is so nice to have coffee on and look at the ocean. Karen was so accommodating and easy to communicate with. We are a family of 6 and easily fit in just two of the bedrooms. The smart tvs were great. We watched a lot of movies and played chess since it’s still very chilly out. It’s incredibly relaxing being so close to the ocean and watching the sunrise. We had a wonderful stay, and will...
Wind Song Getaway on the Beach
Property grounds
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (14)
"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."
Historic Downtown Garden Oasis with Private Patio
Fridge, microwave, oven, stovetop
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (15)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
Beach nearby
Bowers Beach Vacation Rental: 2 Blocks Away!
10.0 out of 10, Exceptional, (1)
"Great place for us. Appreciate the bottled water dispenser and extra water bottle. Only thing I could say that was negative was the master bed mattress was way too soft and gave my wife and I some neck soreness. All in all we really enjoyed our stay."
Bowers Beach Vacation Rental: 2 Blocks Away!
Fridge, microwave, stovetop, cookware/dishes/utensils
Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parking
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (35)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Fridge, microwave, oven, stovetop
Captain's Quarters
9.8 out of 10, Exceptional, (63)
"The property lived up yo expectations. I had been looking at it for a while to rent. My friends and I had enjoyable stay in April. Beds and furniture were comfortable. Hope to stay here again in the future."
Captain's Quarters
Sun-loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (89)
"Lovely visit. I have a 1 and 3 year old. They loved the water and meeting the llama. The room set up is confusing in the listing. Its 3 bedrooms with 2person beds and a forth bedroom w a 1person bed."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Property grounds
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is €156
includes taxes & fees
27 May - 28 May
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Pool
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (12)
"We were in town for a family wedding. The house was spotless, well-stocked and centrally located for our trip. We recommend the property and would come again!"
Grasonville Home w/ Private Pool on the Water
Interior
Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Property grounds
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (2)
"Everything was wonderful & we didn't want to leave! What a Gem! Thank you!"
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Balcony
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
10.0 out of 10, Exceptional, (40)
"Beautiful property. Needs better towels and linens. Kitchen is well equipped. Living areas are spacious and comfortable"
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Fridge, microwave, stovetop, dishwasher
Vibrant Milford Home w/ Boat Dock & Patio!
9.6 out of 10, Exceptional, (10)
"Nice house. Only minor criticisns."
Vibrant Milford Home w/ Boat Dock & Patio!
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See all available properties in Henderson
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.

Other types of properties in Henderson you may be interested in

Front of property
Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, (1307)
"Very nice hotel at a great Thursday price "
The price is €86
includes taxes & fees
27 May - 28 May
Bally's Dover Casino Resort
Exterior
Red Roof Inn & Suites Dover Downtown
2.5 star property
7.4 out of 10, Good, (1002)
"Staff was very courteous, attentive, and helpful. I had a pleasant stay. "
The price is €80
includes taxes & fees
26 May - 27 May
Red Roof Inn & Suites Dover Downtown
Exterior
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, (1000)
"I like the parking it has easy access to your room"
The price is €87
includes taxes & fees
26 May - 27 May
Microtel Inn & Suites by Wyndham 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.

Everything you need to know about Henderson holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Henderson holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Henderson holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Henderson holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Henderson holiday rentals we have selected for you start as low as €156 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Henderson rentals

At Expedia, we put the best Henderson holiday 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 holiday.

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 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?

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : This holiday home rental outside of Henderson is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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

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.

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