Henderson Holiday Rentals from €143: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

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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

Millington

Riley B.

includes taxes & fees

29 Sept - 30 Sept

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.

Dover

Richard B.

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bunk bed, a single bed, a desk, and a chair.

3. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Frederica

nahum f.

includes taxes & fees

12 Oct - 13 Oct

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

4. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

includes taxes & fees

29 Sept - 30 Sept

A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

5. Mini Aruba RV/Glamping Tent

Dover

Robert N.

includes taxes & fees

12 Oct - 13 Oct

A kitchen with wooden cabinets, a dining table, and a refrigerator.

6. Family Retreat at Lansdowne Manor

Centreville

Emily C.

includes taxes & fees

29 Sept - 30 Sept

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

Dover

mark o.

includes taxes & fees

29 Sept - 30 Sept

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

Denton

Glenn S.

includes taxes & fees

8 Oct - 9 Oct

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Rock Hall

lisa p.

includes taxes & fees

29 Sept - 30 Sept

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

10. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with a large island, bar stools, and pendant lighting.

11. Spacious 5 Bedroom w/Pool, Patio and Theater

Magnolia

John K.

A deck with outdoor furniture, a potted plant, and a house in the background.

12. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

"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...

Miriam G.

includes taxes & fees

5 Oct - 6 Oct

A spacious living area with a dining table, sofa, and a kitchen in the background.

13. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

includes taxes & fees

12 Oct - 13 Oct

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

Kitts Hummock

"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...

Alex L.

includes taxes & fees

6 Oct - 7 Oct

A hallway with wooden flooring, a door on the right, and a window at the end.

15. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

includes taxes & fees

30 Sept - 1 Oct

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

16. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

includes taxes & fees

29 Sept - 30 Sept

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

17. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

includes taxes & fees

29 Sept - 30 Sept

A patio with a table and chairs, an umbrella, and a covered grill.

18. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

includes taxes & fees

29 Sept - 30 Sept

A balcony with a view of a grassy field, a white fence, and a building with a grey roof.

19. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

includes taxes & fees

29 Sept - 30 Sept

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Top Henderson Hotel Reviews

Holiday Inn Express Hotel & Suites Dover by IHG

10/10 Excellent

"Everything!!"

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 €143 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 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.

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Check prices for these dates

Our top choices for Henderson holiday rentals

1. Guest Suite for up to 2 in a Victorian on the Chester River

2. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

3. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!