Middletown Vacation Rentals

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Check prices for these dates

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

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 AED 228
AED 528 total
includes taxes & fees
16 Nov - 17 Nov
Columbus Suites
A four-poster bed with a grey headboard, a bedside table with a lamp, and a wall-mounted air conditioner.

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

The Columbus Hotel - The Atelier Suite - 52-303
Middletown
The price is AED 298
AED 698 total
includes taxes & fees
13 Dec - 14 Dec
The Columbus Hotel - The Atelier Suite - 52-303
A hotel room with a bed, bedside tables, a desk, a chair, and a view of the outdoors.

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

The Columbus Hotel - The Scholar Suite - 89-307
Middletown
The price is AED 272
AED 669 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Scholar Suite - 89-307
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.

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

The Columbus Hotel - The Weekender Suite - 52-204
Middletown
The price is AED 257
AED 611 total
includes taxes & fees
14 Nov - 15 Nov
The Columbus Hotel - The Weekender Suite - 52-204
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.

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

The Columbus Hotel - The Market Suite - 52-202
Middletown
The price is AED 272
AED 648 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Market Suite - 52-202
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.

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

The Columbus Hotel - The Canopy Studio - 52-301
Middletown
The price is AED 268
AED 623 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Canopy Studio - 52-301
A modern bedroom with a four-poster bed, a wooden accent wall, a desk with a chair, and a small seating area.

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

The Columbus Hotel - Four-Poster Suite - 52-203
Middletown
The price is AED 261
AED 615 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - Four-Poster Suite - 52-203
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.

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

The Columbus Hotel - The Sunny Studio - 52-302
Middletown
The price is AED 242
AED 594 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Sunny Studio - 52-302
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.

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

The Columbus Hotel - The Reimagined Suite - 52-304
Middletown
The price is AED 220
AED 569 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Reimagined Suite - 52-304
A modern bedroom with a bed, a chair, a small table, and a wardrobe.

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

The Columbus Hotel - The Galley Studio - 89-203
Middletown
The price is AED 283
AED 640 total
includes taxes & fees
10 Dec - 11 Dec
The Columbus Hotel - The Galley Studio - 89-203
A modern kitchen with a stainless steel range hood, a double sink, and a dining area with a table and chairs.

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

The Columbus Hotel - The Sunrise Suite - 89-306
Middletown
The price is AED 257
AED 611 total
includes taxes & fees
10 Dec - 11 Dec
The Columbus Hotel - The Sunrise Suite - 89-306
A modern hotel room with a large bed, a desk, and a chair.

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

The Columbus Hotel - The Tailored Studio - 89-302
Middletown
The price is AED 220
AED 590 total
includes taxes & fees
16 Nov - 17 Nov
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.

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

The Columbus Hotel - The Residence Studio - 89-206
Middletown
The price is AED 228
AED 578 total
includes taxes & fees
16 Nov - 17 Nov
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.

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

The Columbus Hotel - The Revival Suite - 89-304
Middletown
The price is AED 220
AED 569 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The Revival Suite - 89-304
A laundry room with a front-loading washer and dryer, a wooden staircase, and a white door.

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

The Columbus Hotel - The District Studio - 89-204
Middletown
The price is AED 220
AED 569 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - The District Studio - 89-204
A modern bedroom with a bed, a desk, a chair, a lamp, and a window.

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

The Columbus Hotel - Golden Hour Studio - 89-305
Middletown
The price is AED 206
AED 553 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Hotel - Golden Hour Studio - 89-305
A laundry room with a front-loading washer and dryer, a wooden staircase, and a white door.

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

The Columbus Suites | The Workday Studio | 89-202
Middletown
The price is AED 257
AED 611 total
includes taxes & fees
16 Nov - 17 Nov
The Columbus Suites | The Workday Studio | 89-202
A modern kitchen with a built-in microwave and a dining area with a table and chairs.

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

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is AED 298
AED 673 total
includes taxes & fees
14 Dec - 15 Dec
The Columbus Hotel - The Courtyard Suite - 89-303
A bedroom with a four-poster bed, a desk with a chair, and a grey sofa.

19. The Columbus Hotel - The Balcony Suite - 52-201

The Columbus Hotel - The Balcony Suite - 52-201
Middletown
The price is AED 327
AED 665 total
includes taxes & fees
14 Dec - 15 Dec
The Columbus Hotel - The Balcony Suite - 52-201
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.

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

The Columbus Hotel - The Upper Studio - 52-402
Middletown
The price is AED 298
AED 657 total
includes taxes & fees
13 Dec - 14 Dec
The Columbus Hotel - The Upper Studio - 52-402
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

A garden with a rock fountain surrounded by various plants and flowers.
John H Wallace House

John H Wallace House

John H Wallace House
Milford

10/10 Excellent

John and Linda are wonderful hosts, and it's a wonderful place!
United States
David
Reviewed July 28, 2026
John H Wallace House

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.