Henderson Vacation Rentals

Q: What are some of the best vacation home rentals that Henderson has to offer?

Captain's Quarters : This vacation home rental near Henderson is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Dates

November 2026

December 2026

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Our top choices for Henderson vacation 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

Quinton

$110 nightly

Nov 9 - Nov 10

Total with taxes and fees

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.

$138 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

3. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

$136 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

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

Frederica

nahum f.

$248 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

5. Family Retreat at Lansdowne Manor

Centreville

Emily C.

$249 nightly

Nov 9 - Nov 10

Total with taxes and fees

A two-story house with a porch, two windows, and a door.

6. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Denton

Dallas S.

$329 nightly

Dec 1 - Dec 2

Total with taxes and fees

A garden path leading to a wooden building with a rustic appearance.

7. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

$263 nightly

Nov 6 - Nov 7

Total with taxes and fees

A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

8. 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.

$261 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

9. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

Dover

mark o.

$581 nightly

Nov 9 - Nov 10

Total with taxes and fees

A house with a blue front door, two windows, and a small porch.

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

Rock Hall

lisa p.

$251 nightly

Nov 6 - Nov 7

Total with taxes and fees

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.

11. Turnbridge Manor

Denton

Jessica H.

$549 nightly

Nov 9 - Nov 10

Total with taxes and fees

A single-story house with a garage, a front lawn, and a driveway.

12. A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford

Milford

$281 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Susan A.

$290 nightly

Nov 8 - Nov 9

Total with taxes and fees

A room with a bed, a hammock, a window with curtains, a small table, and a basket.

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.

$349 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered porch with a wooden bench, potted plants, and a decorative railing.

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

Chestertown

Mandy D.

$440 nightly

Nov 7 - Nov 8

Total with taxes and fees

A kitchen with wooden cabinets, a stove, and a dining table with chairs.

16. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

$293 nightly

Nov 6 - Nov 7

Total with taxes and fees

A dining area with a round table, chairs, a chandelier, and patterned wallpaper.

17. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

$699 nightly

Nov 8 - Nov 9

Total with taxes and fees

18. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

$732 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

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

Magnolia

John K.

$697 nightly

Nov 30 - Dec 1

Total with taxes and fees

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Find vacation rentals that suit your style

Top Henderson Hotel Reviews

A modern lobby with a grey sofa, blue armchairs, and a small table. There are artwork on the walls and a map.

Holiday Inn Express Hotel & Suites Dover by IHG

Dover

10/10 Excellent

Melissa

A spacious hotel lobby with multiple dining tables, comfortable seating, a large TV screen, and modern lighting fixtures.

Hilton Garden Inn Dover

Dover

10/10 Excellent

Karen

A hotel room with a kitchenette, a bathroom, a living area with a sofa and a bed, and a television.

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

Harrington

10/10 Excellent

I checked in very late (past 10:00pm) and was in no mood to deal with humanity in general. I walked in and the receptionist immediately noted my exhaustion and had everything squared away for me in under five minutes! Mood greatly improved, I asked if they had room service because I was starving. I was informed that it was too late for food to be ordered there but she provided me with four different options of local restaurants that were still open and delivered directly to the hotel. Very...

Anonymous traveler

A spacious lobby with a central fountain, marble flooring, and columns with greenery.

Bally's Dover Casino Resort

Dover

10/10 Excellent

Kimberly

A swimming pool with a metal ladder, lounge chairs, and a small building in the background.

Best Western Denton Inn

Denton

10/10 Excellent

rich

A hotel room with a bed, a sofa, a desk, and a TV.

Comfort Inn & Suites Dover near Speedway

Dover

10/10 Excellent

I really love, the young man who check us in. He was very friendly, and made sure we had what we needed & needed to know. Due to COVID lobby stay clean. Housekeeper: what I dislike was the half clean all the mirrors were marked up and that makes me feel like other things weren't wiped down from being experienced of housekeeping myself, but other than that, my bed was clean, toliet & tub. Setup was nice for walk-in

Dana

A modern dining area with a long table, multiple chairs, and pendant lighting.

Hampton Inn Dover

Dover

10/10 Excellent

Anonymous traveler

A patio area with outdoor seating, a fire feature, and a stone wall.

Residence Inn Marriott Dover

Dover

10/10 Excellent

This was my first time staying at a Residence Inn. It was tucked away behind the Fairfield Inn (also owned by Marriot) and it was difficult to see directly from the road. However, once inside, we were greeted by an exceptionally friendly and welcoming staff. I explained that I was there to visit my sick father in the hospital which the front desk person empathized. I really appreciated this. The place was clean, holiday decorated and felt safe. Breakfast was delicious and warm. Breakfast staff...

Tracey

An outdoor seating area with a fire pit, lounge chairs, and a covered patio.

Home2 Suites by Hilton Dover, DE

Dover

10/10 Excellent

Reginald

A lobby with a sofa, two armchairs, a coffee table, and a floor lamp. There is a painting on the wall and a door leading outside.

Sleep Inn & Suites Dover University Area

Dover

10/10 Excellent

ronald

A MainStay Suites hotel with a covered entrance, brick facade, and a clear blue sky.

MainStay Suites Dover

Dover

10/10 Excellent

Anonymous traveler

A hotel lobby with a fireplace, seating area, and a television.

Comfort Inn & Suites Chestertown

Chestertown

10/10 Excellent

Laura

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

An indoor swimming pool with clear views through large windows, wooden ceiling beams, and a seating area with tables and chairs.

Quality Inn & Suites Harrington - Milford

Harrington

10/10 Excellent

Cutter

Find out more about Henderson

Everything you need to know about Henderson vacation rentals

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

Henderson vacation 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 low season months. For more hustle and bustle, you may prefer to visit Henderson in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $116 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Henderson rentals

At Expedia, we put the best Henderson vacation 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 vacation.

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 vacation rentals in Henderson?

Yes, you can find vacation rentals close to the most popular local attractions in Henderson, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Henderson has to offer?

Captain's Quarters: This vacation home rental near Henderson is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 Saulsbury Road Park. In the larger area, you’ll find Killens Pond State Park and Air Mobility Command Museum.

What’s a vacation rental in Henderson like?

A vacation rental is a private property where you can stay for short or long periods in Henderson. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family getaway.

Henderson Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Henderson vacation 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. First Floor Studio Apartment in Historic Chestertown

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

5. Family Retreat at Lansdowne Manor

6. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

7. Secluded Cottage in Middle of Chestertown

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

9. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

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

11. Turnbridge Manor

12. A pleasant 3-bedroom house in a peaceful, quiet neighborhood in Milford

13. Newly restored apartment in the heart of Chestertown

14. Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

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

16. Family Friendly Cozy 3 Bedroom Duplex

17. Walk to Bowers Beach! Peaceful Coastal Retreat

18. Walk to Bowers Beach! Peaceful Coastal Retreat

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

Find vacation rentals that suit your style

Top Henderson Hotel Reviews

Holiday Inn Express Hotel & Suites Dover by IHG

10/10 Excellent

Find out more about Henderson

Everything you need to know about Henderson vacation rentals

Henderson vacation rentals: An excellent choice for every season

How to find incredible deals on Henderson rentals

Frequently Asked Questions

Are there vacation rentals in Henderson?

What are some of the best vacation home rentals that Henderson has to offer?

What’s there to see and do in Henderson?

What’s a vacation rental in Henderson like?