Henderson Holiday Rentals from AU$230: 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 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

21 Oct - 22 Oct

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

21 Oct - 22 Oct

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.

includes taxes & fees

19 Oct - 20 Oct

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.

includes taxes & fees

28 Oct - 29 Oct

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

5. Family Retreat at Lansdowne Manor

Centreville

Emily C.

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

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

Magnolia

John K.

A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

7. Welcome to the secluded waterfront oasis

Millington

Destiny H.

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

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.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

18 Oct - 19 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

27 Oct - 28 Oct

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

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

Rock Hall

lisa p.

includes taxes & fees

17 Oct - 18 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.

12. Turnbridge Manor

Denton

Jessica H.

includes taxes & fees

3 Nov - 4 Nov

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.

includes taxes & fees

27 Oct - 28 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

25 Oct - 26 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

27 Oct - 28 Oct

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

16. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

includes taxes & fees

18 Oct - 19 Oct

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

17. Walk to Bowers Beach! Peaceful Coastal Retreat

Frederica

includes taxes & fees

26 Oct - 27 Oct

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Top Henderson Hotel Reviews

Microtel Inn & Suites by Wyndham Dover

10/10 Excellent

"No faults found. The room and property were very clean. Everything worked. The staff was professional, courteous and very helpful. The breakfast area was very sanitary and stocked with everything needed for a quick cold breakfast with a few warm/hot items like coffee/tea, oatmeal, and toasted bread or bagels. There were no eggs of any kind or meats, but we did not miss that. The room was well appointed with microwave, small refrigerator and even a pull-out sofa bed that we did not use. We did use the laundry room on the 3rd floor. Only 1 washer and 1 dryer, but no one else needed it for the hour that we used it. Very reasonable at $1.75 for a large front loader washer @ the medium wash cycle and $1.50 for a 45-minute drying cycle. We were totally pleased with our experience"

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."

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, 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 favourite 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 depend 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 AU$230 per night. Entering your travel dates in the search wizard might find you 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 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. 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. Spacious 5 Bedroom w/Pool, Patio and Theater

7. Welcome to the secluded waterfront oasis

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. Secluded Cottage in Middle of Chestertown

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

12. Turnbridge Manor

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. Walk to Bowers Beach! Peaceful Coastal Retreat

17. Walk to Bowers Beach! Peaceful Coastal Retreat

Find holiday rentals that suit your style

Top Henderson Hotel Reviews

Microtel Inn & Suites by Wyndham Dover

Quality Inn & Suites Harrington - Milford

Red Roof Inn & Suites Dover Downtown

Quality Inn Grasonville near Kent Island

Best Western Plus Easton Inn & Suites

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

Find out more about Henderson

Frequently asked questions

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