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
$154 nightly
The price is $174
Oct 13 - Oct 14
Total with taxes and fees
Cottage Suites
A bedroom with a four-poster bed, a desk with a chair, a television on the wall, and two windows.

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

The Columbus Hotel - The Sunny Studio - 52-302
Middletown
$177 nightly
The price is $200
Sep 27 - Sep 28
Total with taxes and fees
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.

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

The Columbus Hotel - The Revival Suite - 89-304
Middletown
$168 nightly
The price is $190
Sep 27 - Sep 28
Total with taxes and fees
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.

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

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
$175 nightly
The price is $198
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Courtyard Suite - 89-303
A compact kitchen with dark cabinets, a stainless steel refrigerator, and a microwave.

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

The Columbus Hotel - The Gold Suite - 89-207
Middletown
$215 nightly
The price is $243
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Gold Suite - 89-207
An open door leading to a deck with outdoor furniture and a stone wall.

6. 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.
$354 nightly
The price is $401
Oct 5 - Oct 6
Total with taxes and fees
Hello Small Stone
A modern bedroom with a four-poster bed, a bedside table with a lamp, a small plant, and a view of buildings outside.

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

The Columbus Hotel - Four-Poster Suite - 52-203
Middletown
$172 nightly
The price is $194
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - Four-Poster Suite - 52-203
A modern bedroom with a bed, bedside tables, a desk, and chairs.

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

The Columbus Hotel - The City Suite - 89-201
Middletown
$179 nightly
The price is $203
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The City Suite - 89-201
A modern bedroom with a four-poster bed, a desk with chairs, and artwork on the walls.

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

The Columbus Hotel - The Market Suite - 52-202
Middletown
$176 nightly
The price is $199
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Market Suite - 52-202
A hallway with a staircase, a laundry room with two washing machines, and a fire alarm on the wall.

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

The Columbus Hotel - The Tailored Studio - 89-302
Middletown
$169 nightly
The price is $191
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Tailored Studio - 89-302
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.

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

The Columbus Hotel - The Weekender Suite - 52-204
Middletown
$179 nightly
The price is $203
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Weekender Suite - 52-204
A modern kitchen with dark cabinetry, a stainless steel refrigerator, and a built-in microwave.

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

The Columbus Hotel - The Scholar Suite - 89-307
Middletown
$177 nightly
The price is $200
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Scholar Suite - 89-307
A modern kitchen with stainless steel appliances, a dining area with a patterned rug, and a door with a number.

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

The Columbus Hotel - The Galley Studio - 89-203
Middletown
$172 nightly
The price is $194
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Galley Studio - 89-203
A bedroom with a bed, a desk, a chair, a window with a view, and a wall-mounted TV.

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

The Columbus Hotel - The District Studio - 89-204
Middletown
$164 nightly
The price is $185
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The District Studio - 89-204
A bedroom with a four-poster bed, a desk with a chair, a television on the wall, and two windows.

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

The Columbus Hotel - The Reimagined Suite - 52-304
Middletown
$168 nightly
The price is $190
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Reimagined Suite - 52-304
A bedroom with a bed, bedside tables, a desk, and a chair.

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

The Columbus Hotel - The Residence Studio - 89-206
Middletown
$198 nightly
The price is $224
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Residence Studio - 89-206
A hallway with a door labeled '204' and a door with a visible lock.

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

The Columbus Hotel - The Upper Studio - 52-402
Middletown
$179 nightly
The price is $203
Sep 27 - Sep 28
Total with taxes and fees
The Columbus Hotel - The Upper Studio - 52-402
A room with a grey armchair, a small round table with a black top and gold legs, and a white conical base.

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

The Columbus Hotel - The Canopy Studio - 52-301
Middletown
$215 nightly
The price is $243
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Canopy Studio - 52-301
A two-story building with a garage and a small attached structure.

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

The Columbus Hotel - The Sunrise Suite - 89-306
Middletown
$215 nightly
The price is $243
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Sunrise Suite - 89-306
A modern living room with a dark door, a grey sofa, and two framed artworks on the wall.

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

The Columbus Hotel - The Balcony Suite - 52-201
Middletown
$230 nightly
The price is $260
Oct 13 - Oct 14
Total with taxes and fees
The Columbus Hotel - The Balcony Suite - 52-201
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

Resorts World Catskills Casino

Resorts World Catskills Casino

8/10 Good
"Great view and staff are courteous. However, there appears to be certain deferred maintenance, especially the bath room."
Laurence 1-night trip
Posted 3 hours ago
Resorts World Catskills Casino

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 $236 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.

Explore a world of travel with Expedia

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.