Beautiful Autumn View in Bear Mountain State Park

Middletown Vacation Rentals

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Check prices for these dates

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

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 ￥23,731
￥64,684 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥15,286
￥29,012 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥70,059
￥86,259 total
includes taxes & fees
Aug 17 - Aug 18
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 ￥17,852
￥32,621 total
includes taxes & fees
Sep 8 - Sep 9
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 nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is ￥47,160
￥88,341 total
includes taxes & fees
Aug 31 - Sep 1
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 ￥14,191
￥23,075 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥135,380
￥232,915 total
includes taxes & fees
Aug 17 - Aug 18
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 ￥14,191
￥24,703 total
includes taxes & fees
Aug 18 - Aug 19
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 ￥71,244
￥87,721 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥23,652
￥47,235 total
includes taxes & fees
Aug 14 - Aug 15
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 ￥47,722
￥58,758 total
includes taxes & fees
Aug 19 - Aug 20
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 ￥21,501
￥37,767 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥27,856
￥50,526 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥33,765
￥82,279 total
includes taxes & fees
Aug 30 - Aug 31
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 ￥23,652
￥40,715 total
includes taxes & fees
Aug 20 - Aug 21
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, (36 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is ￥27,952
￥46,577 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥157,808
￥262,769 total
includes taxes & fees
Aug 24 - Aug 25
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 ￥22,809
￥48,920 total
includes taxes & fees
Aug 21 - Aug 22
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 ￥27,206
￥45,522 total
includes taxes & fees
Aug 16 - Aug 17
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 ￥20,068
￥44,503 total
includes taxes & fees
Aug 17 - Aug 18
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

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"10 of 10"
Howard 2-night trip
Posted 2 hours 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?

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.