Henderson Holiday Rentals from NZ$283: 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.

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Our top choices for Henderson holiday rentals

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

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

Dover

Richard B.

includes taxes & fees

12 Oct - 13 Oct

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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

Millington

Riley B.

includes taxes & fees

6 Oct - 7 Oct

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.

3. Turnbridge Manor

Denton

Glenn S.

includes taxes & fees

6 Oct - 7 Oct

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

4. Mini Aruba RV/Glamping Tent

Dover

Robert N.

includes taxes & fees

12 Oct - 13 Oct

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

5. 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

6 Oct - 7 Oct

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

6. 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

12 Oct - 13 Oct

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

2 Nov - 3 Nov

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

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

Frederica

nahum f.

includes taxes & fees

4 Nov - 5 Nov

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

9. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

includes taxes & fees

7 Oct - 8 Oct

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

8 Oct - 9 Oct

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

11. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

includes taxes & fees

6 Oct - 7 Oct

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

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

Chestertown

Mandy D.

includes taxes & fees

7 Oct - 8 Oct

A round window with a view of a garden, a tree, and a building in the background.

13. 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

18 Oct - 19 Oct

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

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

Rock Hall

lisa p.

includes taxes & fees

13 Oct - 14 Oct

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

15. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

includes taxes & fees

6 Oct - 7 Oct

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Top Henderson Hotel Reviews

Quality Inn Grasonville near Kent Island

8/10 Good

"Bed was very comfortable and the bedding was clean/new. Breakfast was great. Right off Rt 50 with a Dennys only steps away. Minor flaws- no elevator and the vending machines only took cash."

Best Western Plus Easton Inn & Suites

8/10 Good

"Very good location, there was variety at breakfast and the food and coffee very good. The room was in very good condition; there was not enough lighting in the room or bathroom. The toilet paper and tissues were very cheap. Overall our experience was very good and we enjoyed our stay."

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

8/10 Good

"Room was mostly clean but definitely had a pet odor in it. We had to burn candles to lessen the odor when we were in the room. Had an issue when we had to extend our trip a day because we had used Expedia. We were able to get another reservation and spoke directly to the front desk about staying in the same room and not being disturbed. (This was a working trip and we had been up almost 26 hours which is why we wanted everything set when we got to the hotel to sleep) We were guaranteed everything was set. The next morning housekeeping knocked on our door (waking us up) and then about 30 minutes later the front desk called, waking us up a second time. They apologized, but that isn’t much of a consolation when all you needed was sleep. Parking was great, and staff were nice. The breakfast was also good."

Quality Inn Smyrna

10/10 Excellent

"The staff is friendly. The property and rooms immaculate. The parking lot is clean and plenty of parking. The location is ideal for grocery shopping, fast food, gas and entertainment. I’ve stayed at this location on three occasions it has been a great experience each time. I will definitely stay again. Great place."

Find out more about Henderson

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Henderson holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Henderson. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Henderson. Seeing all the best attractions is bound to make you fall in love with Henderson. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Henderson short-term rentals, that won’t be hard to do.

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

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

3. Turnbridge Manor

4. Mini Aruba RV/Glamping Tent

5. First Floor Studio Apartment in Historic Chestertown

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

7. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

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

9. Newly restored apartment in the heart of Chestertown

10. Secluded Cottage in Middle of Chestertown

11. Walk to Bowers Beach! Peaceful Coastal Retreat

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

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

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

15. Walk to Bowers Beach! Peaceful Coastal Retreat

Find holiday rentals that suit your style

Top Henderson Hotel Reviews

Quality Inn Grasonville near Kent Island

Red Roof Inn & Suites Dover Downtown

Bally's Dover Casino Resort

Microtel Inn & Suites by Wyndham Dover

Best Western Plus Easton Inn & Suites

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

Comfort Suites Dover University Area

Quality Inn Smyrna

Harrington Welcome Inn

Find out more about Henderson

Frequently asked questions

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