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
$127 nightly
The price is $144
Nov 16 - Nov 17
Total with taxes and fees
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
$131 nightly
The price is $149
Nov 11 - Nov 12
Total with taxes and fees
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
$137 nightly
The price is $155
Nov 16 - Nov 17
Total with taxes and fees
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
$143 nightly
The price is $162
Nov 16 - Nov 17
Total with taxes and fees
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
$162 nightly
The price is $183
Dec 10 - Dec 11
Total with taxes and fees
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
$135 nightly
The price is $153
Nov 11 - Nov 12
Total with taxes and fees
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
$137 nightly
The price is $155
Nov 16 - Nov 17
Total with taxes and fees
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
$150 nightly
The price is $170
Nov 11 - Nov 12
Total with taxes and fees
The Columbus Hotel - The Market Suite - 52-202
Room

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

The Columbus Hotel - Four-Poster Suite - 52-203
Middletown
$143 nightly
The price is $162
Nov 11 - Nov 12
Total with taxes and fees
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
$150 nightly
The price is $170
Nov 16 - Nov 17
Total with taxes and fees
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
$142 nightly
The price is $161
Nov 16 - Nov 17
Total with taxes and fees
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
$142 nightly
The price is $160
Nov 11 - Nov 12
Total with taxes and fees
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
$155 nightly
The price is $175
Nov 11 - Nov 12
Total with taxes and fees
The Columbus Hotel - The Scholar Suite - 89-307
A modern kitchen with a stainless steel refrigerator, a double sink, and dark wooden cabinets.

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

The Columbus Hotel - Golden Hour Studio - 89-305
Middletown
$133 nightly
The price is $150
Nov 16 - Nov 17
Total with taxes and fees
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
$173 nightly
The price is $196
Dec 10 - Dec 11
Total with taxes and fees
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
$149 nightly
The price is $169
Nov 16 - Nov 17
Total with taxes and fees
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
$152 nightly
The price is $172
Nov 16 - Nov 17
Total with taxes and fees
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
$159 nightly
The price is $180
Nov 16 - Nov 17
Total with taxes and fees
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
$162 nightly
The price is $183
Dec 10 - Dec 11
Total with taxes and fees
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
$162 nightly
The price is $183
Dec 10 - Dec 11
Total with taxes and fees
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

A large, two-story house with a wrap-around porch and multiple chimneys.
Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast

Parkway House Goshen Family-Friendly Bed & Breakfast
Goshen

10/10 Excellent

It was an amazing stay with such a warm and inviting room. We could see the race track from our window as well. Great options for Spartan racers and travelers planning ahead that was comfort and cleanliness
United States
Matthew
Reviewed November 7, 2026
Parkway House Goshen Family-Friendly Bed & Breakfast

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 Middletown 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 Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. 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

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.

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