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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
6.6 out of 10, (19 reviews)
"It was a great place "
United States
Jose
The price is P5,021
P10,295 total
includes taxes & fees
Oct 13 - Oct 14
Cottage Suites
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

2. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
The price is P17,605
P21,677 total
includes taxes & fees
Oct 14 - Oct 15
Carriage House Apartment Goshen NY
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

3. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (2 reviews)
"This location was perfect for our yearly fall gathering. It is 15 minutes from Pure Terror Scream Park and nestled in a historic town. The unit was clean, spacious, and perfect for a group of 7-8 people. The hosts were very helpful and prompt with instructions. I would recommend this stay if you are looking to stay in Goshen, NY."
United States
Tammy
The price is P19,302
P23,765 total
includes taxes & fees
Oct 12 - Oct 13
Hay Loft Apartment in Barn - Goshen
A two-story house with a porch, a table, and chairs outside.

4. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is P14,630
P18,014 total
includes taxes & fees
Oct 13 - Oct 14
Historic Horse Barn Apartment in Goshen
A wooden cabin with a porch, a door, and a window.

5. Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
3.0 star property
Westbrookville
The price is P9,414
P14,993 total
includes taxes & fees
Oct 12 - Oct 13
Close to Trails: Studio w/ Water Views
An indoor water park with a large water slide, inflatable tubes, and lush greenery.

6. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
The price is P15,755
P74,163 total
includes taxes & fees
Oct 15 - Oct 16
2 Lake Cabins Pool+hottub Game Room 23acs
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

7. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is P13,306
P21,567 total
includes taxes & fees
Oct 13 - Oct 14
Hike & Fish: Outdoor Retreat Near Trails
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

8. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is P23,285
P43,831 total
includes taxes & fees
Oct 22 - Oct 23
Bright Cornwall-on-hudson Vacation Rental!
A house with a covered porch, stone foundation, and a front door with a wreath.

9. West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is P55,442
P100,485 total
includes taxes & fees
Oct 15 - Oct 16
West Point Summer Pool Jacuzzi Events Pets OK
A spacious living room with a large sectional sofa, a stone fireplace, and a wooden ceiling.

10. Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
3.0 star property
Vernon
Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
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 Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"Incredible staff. Great location. Attention to guests superlative.West Point tours were fantastic. Only complaint was that it is extremely pricey. Which is understandable considering where we stayed. We ate there for 2 dinners, one lunch, and 1 breakfast. Meals are expensive but were great except for a breakfast that was stone-cold for $24 each."
Cameron 3-night trip
Posted 1 hour ago
The Thayer Hotel at 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
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • 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.

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.