A lake surrounded by autumn-colored trees reflecting on the water.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middletown vacation rentals

A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

1. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is ￥9,841
￥22,804 total
includes taxes & fees
Nov 16 - Nov 17
Columbus Suites
A modern hotel room with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view of the adjacent dining area.

2. The Columbus Hotel - The Reimagined Suite - 52-304

The Columbus Hotel - The Reimagined Suite - 52-304
Middletown
The price is ￥8,769
￥23,746 total
includes taxes & fees
Nov 12 - Nov 13
The Columbus Hotel - The Reimagined Suite - 52-304
A laundry room with a front-loading washer and dryer, a wooden staircase, and a white door.

3. The Columbus Hotel - The Revival Suite - 89-304

The Columbus Hotel - The Revival Suite - 89-304
Middletown
The price is ￥9,523
￥24,600 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Revival Suite - 89-304
A modern hotel room with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view of the adjacent dining area.

4. The Columbus Hotel - The Sunny Studio - 52-302

The Columbus Hotel - The Sunny Studio - 52-302
Middletown
The price is ￥10,476
￥25,678 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Sunny Studio - 52-302
A modern bedroom with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view into the adjacent dining area.

5. The Columbus Hotel - The Upper Studio - 52-402

The Columbus Hotel - The Upper Studio - 52-402
Middletown
The price is ￥13,491
￥29,088 total
includes taxes & fees
Dec 10 - Dec 11
The Columbus Hotel - The Upper Studio - 52-402
A laundry room with a front-loading washer and dryer, a wooden staircase, and a white door.

6. The Columbus Hotel - The Residence Studio - 89-206

The Columbus Hotel - The Residence Studio - 89-206
Middletown
The price is ￥9,841
￥24,959 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Residence Studio - 89-206
A laundry room with a front-loading washer and dryer, a wooden staircase, and a white door.

7. The Columbus Hotel - The District Studio - 89-204

The Columbus Hotel - The District Studio - 89-204
Middletown
The price is ￥9,523
￥24,600 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The District Studio - 89-204
A modern bedroom with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view into the adjacent dining area.

8. The Columbus Hotel - The Market Suite - 52-202

The Columbus Hotel - The Market Suite - 52-202
Middletown
The price is ￥10,928
￥27,087 total
includes taxes & fees
Nov 12 - Nov 13
The Columbus Hotel - The Market Suite - 52-202
A modern bedroom with a four-poster bed, a wooden accent wall, a desk with a chair, and a small seating area.

9. The Columbus Hotel - Four-Poster Suite - 52-203

The Columbus Hotel - Four-Poster Suite - 52-203
Middletown
The price is ￥11,269
￥26,574 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - Four-Poster Suite - 52-203
A modern bedroom with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view into the adjacent dining area.

10. The Columbus Hotel - The Canopy Studio - 52-301

The Columbus Hotel - The Canopy Studio - 52-301
Middletown
The price is ￥11,587
￥26,934 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Canopy Studio - 52-301
A modern hotel room with a large bed, a desk, and a chair.

11. The Columbus Hotel - The Tailored Studio - 89-302

The Columbus Hotel - The Tailored Studio - 89-302
Middletown
The price is ￥9,523
￥25,498 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Tailored Studio - 89-302
A laundry room with a front-loading washer and dryer, a wooden staircase, and a white door.

12. The Columbus Suites | The Workday Studio | 89-202

The Columbus Suites | The Workday Studio | 89-202
Middletown
The price is ￥10,388
￥25,578 total
includes taxes & fees
Nov 12 - Nov 13
The Columbus Suites | The Workday Studio | 89-202
A hotel room with a bed, bedside tables, a desk, a chair, and a view of the outdoors.

13. The Columbus Hotel - The Scholar Suite - 89-307

The Columbus Hotel - The Scholar Suite - 89-307
Middletown
The price is ￥10,928
￥27,984 total
includes taxes & fees
Nov 12 - Nov 13
The Columbus Hotel - The Scholar Suite - 89-307
A modern bedroom with a bed, a desk, a chair, a lamp, and a window.

14. The Columbus Hotel - Golden Hour Studio - 89-305

The Columbus Hotel - Golden Hour Studio - 89-305
Middletown
The price is ￥8,888
￥23,881 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - Golden Hour Studio - 89-305
A modern kitchen with a built-in microwave and a dining area with a table and chairs.

15. The Columbus Hotel - The Courtyard Suite - 89-303

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is ￥13,491
￥31,063 total
includes taxes & fees
Dec 10 - Dec 11
The Columbus Hotel - The Courtyard Suite - 89-303
A four-poster bed with a grey headboard, a bedside table with a lamp, and a wall-mounted air conditioner.

16. The Columbus Hotel - The Atelier Suite - 52-303

The Columbus Hotel - The Atelier Suite - 52-303
Middletown
The price is ￥9,841
￥26,754 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Atelier Suite - 52-303
A modern kitchen with a stainless steel range hood, a double sink, and a dining area with a table and chairs.

17. The Columbus Hotel - The Sunrise Suite - 89-306

The Columbus Hotel - The Sunrise Suite - 89-306
Middletown
The price is ￥11,904
￥27,293 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Sunrise Suite - 89-306
A modern bedroom with a bed, a chair, a small table, and a wardrobe.

18. The Columbus Hotel - The Galley Studio - 89-203

The Columbus Hotel - The Galley Studio - 89-203
Middletown
The price is ￥13,015
￥28,551 total
includes taxes & fees
Nov 16 - Nov 17
The Columbus Hotel - The Galley Studio - 89-203
A modern bedroom with a four-poster bed, a wooden accent wall, a bedside table with a lamp, and a view into the adjacent dining area.

19. The Columbus Hotel - The Weekender Suite - 52-204

The Columbus Hotel - The Weekender Suite - 52-204
Middletown
The Columbus Hotel - The Weekender Suite - 52-204
A modern bedroom with a large bed, a TV, a desk, and a window.

20. The Columbus Suites | The Landing Studio | 89-201

The Columbus Suites | The Landing Studio | 89-201
Middletown
The Columbus Suites | The Landing Studio | 89-201
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"It was really clean and staff were very friendly"
Brian 1-night trip
Posted 2 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals in Middletown close to Orange County Fairgrounds, or you can go with a more remote option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and shops in Middletown. Make sure you have time to check out the churches and architecture during your trip.

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental outside of Middletown is located on a lake and has an outdoor pool, a balcony, 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Middletown?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Highland Lake and Thomas Bull Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Paramount Theatre is one of the cultural attractions. Orange County Fair Speedway and Orange County Fairgrounds are other places to visit while you're in town.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for short or long periods in Middletown. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.