Henderson Vacation Rentals from AED 348: Search Short-Term 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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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

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

2. Family Retreat at Lansdowne Manor

Centreville

Emily C.

A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

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

Dover

Richard B.

AED 556 total

includes taxes & fees

29 Nov - 30 Nov

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.

4. Turnbridge Manor

Denton

Jessica H.

AED 2,305 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Denton

Dallas S.

AED 1,281 total

includes taxes & fees

1 Dec - 2 Dec

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

6. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

Dover

mark o.

AED 2,188 total

includes taxes & fees

20 Nov - 21 Nov

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

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

Magnolia

John K.

AED 2,668 total

includes taxes & fees

30 Nov - 1 Dec

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

8. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

AED 552 total

includes taxes & fees

16 Nov - 17 Nov

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

9. 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.

AED 1,012 total

includes taxes & fees

11 Dec - 12 Dec

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

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

Frederica

nahum f.

AED 996 total

includes taxes & fees

13 Dec - 14 Dec

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

11. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

AED 1,231 total

includes taxes & fees

15 Nov - 16 Nov

12. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

AED 2,688 total

includes taxes & fees

15 Nov - 16 Nov

13. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

AED 2,552 total

includes taxes & fees

15 Nov - 16 Nov

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.

AED 1,256 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Milford

AED 1,061 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Rock Hall

lisa p.

AED 1,072 total

includes taxes & fees

9 Dec - 10 Dec

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

17. Family Friendly Cozy 3 Bedroom Duplex

Grasonville

AED 1,145 total

includes taxes & fees

25 Nov - 26 Nov

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Find vacation rentals that suit your style

Top Henderson Hotel Reviews

A modern grocery store with refrigerated sections for chilled and frozen items, shelves stocked with beverages, and a coffee machine.

Hilton Garden Inn Dover

Dover

10/10 Excellent

Karen

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 buffet with various food items, including omelets and other dishes, served in metal containers.

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 hotel lobby with a reception desk, seating area, and a large wall mural.

Best Western Denton Inn

Denton

10/10 Excellent

rich

A spacious lobby with a central fountain, a grand chandelier, and a curved staircase.

Bally's Dover Casino Resort

Dover

10/10 Excellent

Kimberly

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

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 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

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

Hampton Inn Dover

Dover

10/10 Excellent

Anonymous traveler

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

Two Adirondack chairs facing a calm body of water with a clear sky above.

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

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

Change your mind

Treat yourself

Be picky

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. Family Retreat at Lansdowne Manor

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

4. Turnbridge Manor

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

6. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

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

8. First Floor Studio Apartment in Historic Chestertown

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

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

11. Newly restored apartment in the heart of Chestertown

12. Walk to Bowers Beach! Peaceful Coastal Retreat

13. Walk to Bowers Beach! Peaceful Coastal Retreat

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

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

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

17. Family Friendly Cozy 3 Bedroom Duplex

Find vacation rentals that suit your style

Top Henderson Hotel Reviews

Hilton Garden Inn Dover

10/10 Excellent

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?