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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.4 out of 10, (18 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 ￥13,683
￥27,043 total
includes taxes & fees
Oct 13 - Oct 14
Cottage Suites
A bedroom with a bed, a desk, a chair, a window with a view, and a wall-mounted TV.

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

The Columbus Hotel - The District Studio - 89-204
Middletown
The price is ￥13,715
￥30,640 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The District Studio - 89-204
A hallway with a door labeled '302' and a keypad lock.

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

The Columbus Hotel - The Reimagined Suite - 52-304
Middletown
The price is ￥13,589
￥30,497 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Reimagined Suite - 52-304
A modern hotel room with a large bed, a desk, a chair, a TV, and a wardrobe.

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

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is ￥14,470
￥33,273 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Courtyard Suite - 89-303
A compact kitchen with a built-in microwave, a coffee maker, and a stainless steel sink.

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

The Columbus Hotel - The Galley Studio - 89-203
Middletown
The price is ￥15,980
￥33,202 total
includes taxes & fees
Sep 28 - Sep 29
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.

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

The Columbus Hotel - The Weekender Suite - 52-204
Middletown
The price is ￥15,099
￥32,205 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Weekender Suite - 52-204
A hotel room with a large bed, two bedside tables, a wall-mounted air conditioning unit, and a floor lamp.

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

The Columbus Hotel - The Scholar Suite - 89-307
Middletown
The price is ￥16,105
￥35,123 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Scholar Suite - 89-307
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 ￥16,735
￥34,056 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Sunny Studio - 52-302
A hotel room with a bed, a desk, a chair, a TV, and a window with a view of a bridge.

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

The Columbus Hotel - The Revival Suite - 89-304
Middletown
The price is ￥14,973
￥32,063 total
includes taxes & fees
Sep 29 - Sep 30
The Columbus Hotel - The Revival Suite - 89-304
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 Upper Studio - 52-402

The Columbus Hotel - The Upper Studio - 52-402
Middletown
The price is ￥14,973
￥32,063 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Upper Studio - 52-402

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

The Columbus Hotel - Four-Poster Suite - 52-203
Middletown
The price is ￥16,105
￥33,344 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - Four-Poster Suite - 52-203
A kitchen with dark cabinets, a stainless steel refrigerator, a microwave, and a coffee maker.

12. The Columbus Hotel - The City Suite - 89-201

The Columbus Hotel - The City Suite - 89-201
Middletown
The price is ￥15,854
￥33,060 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The City Suite - 89-201
A staircase with a fire alarm and a row of lockers.

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

The Columbus Hotel - The Market Suite - 52-202
Middletown
The price is ￥15,099
￥33,095 total
includes taxes & fees
Sep 28 - Sep 29
The Columbus Hotel - The Market Suite - 52-202
A hallway with a black door labeled '207', a fire alarm, and a laundry room with two washing machines.

14. The Columbus Hotel - The Gold Suite - 89-207

The Columbus Hotel - The Gold Suite - 89-207
Middletown
The price is ￥16,735
￥34,056 total
includes taxes & fees
Sep 29 - Sep 30
The Columbus Hotel - The Gold Suite - 89-207

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

The Columbus Hotel - The Canopy Studio - 52-301
Middletown
The price is ￥17,490
￥34,910 total
includes taxes & fees
Sep 29 - Sep 30
The Columbus Hotel - The Canopy Studio - 52-301
A kitchen with a refrigerator, microwave, and dark cabinets.

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

The Columbus Hotel - The Residence Studio - 89-206
Middletown
The price is ￥16,672
￥33,985 total
includes taxes & fees
Oct 13 - Oct 14
The Columbus Hotel - The Residence Studio - 89-206
A two-story building with a garage and a small attached structure.

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

The Columbus Hotel - The Sunrise Suite - 89-306
Middletown
The price is ￥17,867
￥35,338 total
includes taxes & fees
Sep 30 - Oct 1
The Columbus Hotel - The Sunrise Suite - 89-306
A modern bedroom with a four-poster bed, a sofa, and a small side table.

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

The Columbus Hotel - The Balcony Suite - 52-201
Middletown
The price is ￥19,660
￥37,365 total
includes taxes & fees
Oct 13 - Oct 14
The Columbus Hotel - The Balcony Suite - 52-201
A hallway with a staircase, a laundry room with two washing machines, and a fire alarm on the wall.

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

The Columbus Hotel - The Tailored Studio - 89-302
Middletown
The price is ￥19,660
￥38,255 total
includes taxes & fees
Oct 13 - Oct 14
The Columbus Hotel - The Tailored Studio - 89-302
An open door leading to a deck with outdoor furniture and a stone wall.

20. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is ￥23,450
￥59,445 total
includes taxes & fees
Oct 12 - Oct 13
Hello Small Stone
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

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"Great"
Madeline 1-night trip
Posted 1 hour ago
The Kartrite Resort & Indoor Waterpark

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:

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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.