Beautiful Autumn View in Bear Mountain State Park

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Middletown vacation rentals

Interior

1. Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 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 AED 547
AED 1,492 total
includes taxes & fees
16 Aug - 17 Aug
Hello Small Stone
Suite | Desk, WiFi (free), individually furnished, bed sheets

2. Cottage Suites

Cottage Suites
3.0 star property
Middletown
5.4 out of 10, (10 reviews)
"Room could have actually been cleaned , this is a building not a “hotel” ,"
United States
Jennifer
The price is AED 305
AED 615 total
includes taxes & fees
12 Aug - 13 Aug
Cottage Suites
Apartment, 3 Bedrooms, Kitchen | Living area

3. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is AED 1,616
AED 1,989 total
includes taxes & fees
17 Aug - 18 Aug
Hay Loft Apartment in Barn - Goshen
1 bedroom, WiFi (free), bed sheets

4. Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.6 out of 10, Exceptional, (31 reviews)
"This is a beautiful and quiet space to get away to and was just what I needed for the two nights."
United States
Dan V.
The price is AED 441
AED 789 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Outdoor spa tub

5. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (64 reviews)
"We had a wonderful stay in this beautiful, cozy home. Close to Legoland and many other places to see. Home had all the amenities we needed and my nephew loved the room with the bunk beds and toys. Highly recommend if your visiting the area! "
United States
Sharon W.
The price is AED 1,088
AED 2,037 total
includes taxes & fees
9 Sep - 10 Sep
Country House w/Hot Tub, Deck, Grill & Fire Pit
Interior

6. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (20 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is AED 327
AED 532 total
includes taxes & fees
12 Aug - 13 Aug
Trails Head Tiny House
Outdoor pool, a heated pool

7. Luxury School House Retreat With Pool & Sauna - 1HR from NYC

Luxury School House Retreat With Pool & Sauna - 1HR from NYC
New Hampton
10.0 out of 10, Exceptional, (21 reviews)
"House was great, conveniently located to ski mountain, Hunter was a pleasure to work with, house was clean and had so many amenities for our family! Highly recommend! "
United States
Jennifer P.
The price is AED 2,810
AED 4,894 total
includes taxes & fees
12 Aug - 13 Aug
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
Interior

8. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.4 out of 10, Very Good, (15 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is AED 311
AED 551 total
includes taxes & fees
9 Sep - 10 Sep
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Romantic Duplex, 3 Bedrooms, Kitchen | Private kitchen | Coffee/tea maker, toaster, cleaning supplies, freezer

9. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is AED 1,650
AED 2,032 total
includes taxes & fees
16 Aug - 17 Aug
Carriage House Apartment Goshen NY
Smart TV

10. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is AED 545
AED 1,089 total
includes taxes & fees
14 Aug - 15 Aug
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Design Apartment, Patio, Garden View | View from room

11. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is AED 1,123
AED 1,383 total
includes taxes & fees
19 Aug - 20 Aug
Historic Horse Barn Apartment in Goshen
Interior

12. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (116 reviews)
"Was very pet friendly. "
United States
Kevin
The price is AED 496
AED 871 total
includes taxes & fees
16 Aug - 17 Aug
Trails Head Cabin
Microwave, oven, stovetop, dishwasher

13. Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (20 reviews)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
The price is AED 642
AED 1,169 total
includes taxes & fees
12 Aug - 13 Aug
Modern Hudson Valley Apt 202 - King/Queen/Twin
Cottage (2 Bedrooms) | Interior

14. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is AED 779
AED 1,897 total
includes taxes & fees
30 Aug - 31 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Beach

15. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.8 out of 10, Exceptional, (41 reviews)
"Very thoughtfully appointed and lovingly maintained. Excellent value with lots of extras. I travelled in July, and the lake was amazing"
United States
Olga
The price is AED 545
AED 939 total
includes taxes & fees
20 Aug - 21 Aug
Beaver Lake Escape
Coffee/tea maker, fridge, microwave, oven

16. The Wine House, Sitting atop of Warwick's brand new Wine Bar

The Wine House, Sitting atop of Warwick's brand new Wine Bar
Warwick
10.0 out of 10, Exceptional, (35 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is AED 645
AED 1,074 total
includes taxes & fees
12 Aug - 13 Aug
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Coffee/tea maker, fridge, microwave, oven

17. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
Montgomery
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful home, attentive hosts, and the hot tub was great!"
United States
Kyle F.
The price is AED 3,329
AED 5,651 total
includes taxes & fees
12 Aug - 13 Aug
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
Exterior

18. Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (57 reviews)
"The area is very convenient for doing outdoor activities. Room was clean."
United States
Siyu
The price is AED 526
AED 1,127 total
includes taxes & fees
15 Aug - 16 Aug
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Exterior

19. Walk to Mountain Creek Waterpark! Pool, Hot Tubs, Sauna On-Site!

Walk to Mountain Creek Waterpark! Pool, Hot Tubs, Sauna On-Site!
Vernon Township
10.0 out of 10, Exceptional, (55 reviews)
"Great stay! Easy checkin and checkout and the place is very comfortable and clean!"
United States
Kate K.
The price is AED 652
AED 1,078 total
includes taxes & fees
25 Aug - 26 Aug
Walk to Mountain Creek Waterpark! Pool, Hot Tubs, Sauna On-Site!
1 bedroom, WiFi (free), bed sheets

20. Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (45 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
The price is AED 463
AED 1,018 total
includes taxes & fees
13 Aug - 14 Aug
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
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

Tru by Hilton Middletown

Tru by Hilton Middletown

10/10 Excellent
"The rooms were clean. The staff was very helpful and friendly as well."
Charmaine 2-night trip
Posted 7 hours ago
Tru by Hilton 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?

Cozy Cabin with Sauna & Firepit!: This vacation home rental outside of Middletown offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave.

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?

Thomas Bull Memorial Park and Highland Lake are a couple of scenic spots to enjoy the outdoors, whereas Paramount Theatre is one of the cultural attractions. While in the area, you can also visit popular places like LEGOLAND® New York and Woodbury Common Premium Outlets.

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.