Holiday Rentals in Henderson

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Holiday Rentals in Henderson

Captain's Quarters

9.8 out of 10, Exceptional, (99)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (31)
"Great house for us as always! It fits our needs perfectly !! Thanks for sharing !"
Entire Townhouse in Rock Hall

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

10.0 out of 10, Exceptional, (93)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

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

9.8 out of 10, Exceptional, (9)
"From the time we checked in til we checked out was a pleasure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (101)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is €140
includes taxes & fees
29 Sept - 30 Sept
First Floor Studio Apartment in Historic Chestertown

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (64)
"Had such a great time at this cottage...would definately come back! Close to downtown activities and easy walking to water. Enjoyed our time there!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

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

10.0 out of 10, Exceptional, (13)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is €248
includes taxes & fees
28 Oct - 29 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (5)
"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

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (84)
"We had a wonderful weekend. Thank you!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (57)
"We had an awesome time at the property. The pool and jacuzzi are great for the family to play together. The house has board games and toys for the little ones, plus bikes to explore the little town. We will definitely be back. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2.0 star property
8.6 out of 10, Excellent, (4)
"Would I stay here again? No. Would I recommend it to a friend? Also no.While the unit was clean, it felt quite tired and in need of a refresh. The kitchen was minimally equipped, with very few pots and pans, making it difficult to cook meals. Additionally, there were air fresheners and purifiers in every room, which made us wonder if they were masking an underlying issue. Overall, the space could benefit from some updates and better preparation for guests."
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (4)
"My family had a great time during our stay! The house was very clean and nice. Views were spectacular! Katie was very responsive to all of my questions. "
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

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

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
The price is €383
includes taxes & fees
29 Sept - 30 Sept
HGTV quality, private guest suite, country getaway with hot tub & fire pit

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (39)
"Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too. "
Historic Downtown Garden Oasis with Private Patio

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (33)
"This home is beautiful! Host was responder quickly "
Wind Song Getaway on the Beach

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
Stylish Home on the Choptank River (with Tidal Beach)
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

Find out more about Henderson

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 €140 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?

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 Tilmon's Island Winery 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.