A large steel bridge spanning a river, surrounded by trees and buildings.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Middletown vacation rentals

Suite | Desk, WiFi (free), individually furnished, bed sheets

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.6 out of 10, (7 reviews)
"It was a great place "
United States
Jose
The price is SAR 362
SAR 930 total
includes taxes & fees
20 Jul - 21 Jul
Cottage Suites
Interior

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 SAR 504
SAR 1,432 total
includes taxes & fees
20 Jul - 21 Jul
Hello Small Stone
1 bedroom, WiFi (free), bed sheets

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)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
The price is SAR 456
SAR 809 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Smart TV

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 SAR 558
SAR 1,099 total
includes taxes & fees
20 Jul - 21 Jul
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Interior

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (113 reviews)
"Was very pet friendly. "
United States
Kevin
The price is SAR 439
SAR 798 total
includes taxes & fees
22 Jul - 23 Jul
Trails Head Cabin
Interior

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 SAR 335
SAR 544 total
includes taxes & fees
20 Jul - 21 Jul
Trails Head Tiny House
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (29 reviews)
"The kitchen was great, lots of tools, fun to cook in! "
United States
Brooke H.M. S.
The price is SAR 302
SAR 668 total
includes taxes & fees
20 Jul - 21 Jul
Dream getaway apartment in the foot of Gunks Ridge
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is SAR 368
SAR 621 total
includes taxes & fees
27 Jul - 28 Jul
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is SAR 462
SAR 867 total
includes taxes & fees
22 Jul - 23 Jul
Historic Cabin with Pool & Fire Pit
Interior

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (49 reviews)
"Clean, modern, well designed, convenient to community resources "
United States
Ann B.
The price is SAR 421
SAR 952 total
includes taxes & fees
29 Jul - 30 Jul
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Microwave, oven, stovetop, dishwasher

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 SAR 657
SAR 1,213 total
includes taxes & fees
20 Jul - 21 Jul
Modern Hudson Valley Apt 202 - King/Queen/Twin
Beach

Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (39 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 SAR 558
SAR 948 total
includes taxes & fees
20 Jul - 21 Jul
Beaver Lake Escape
Property grounds

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (87 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is SAR 481
SAR 917 total
includes taxes & fees
10 Aug - 11 Aug
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Apartment, 3 Bedrooms, Kitchen | Living area

Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
The price is SAR 1,943
SAR 2,393 total
includes taxes & fees
20 Jul - 21 Jul
Hay Loft Apartment in Barn - Goshen
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (10 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is SAR 514
SAR 899 total
includes taxes & fees
21 Jul - 22 Jul
TRANQUIL MOUNTAIN SOLITUDE
Coffee/tea maker, fridge, microwave, oven

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, (34 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
The price is SAR 659
SAR 1,090 total
includes taxes & fees
20 Jul - 21 Jul
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Romantic Duplex, 3 Bedrooms, Kitchen | Private kitchen | Coffee/tea maker, toaster, cleaning supplies, freezer

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is SAR 1,885
SAR 2,321 total
includes taxes & fees
20 Jul - 21 Jul
Carriage House Apartment Goshen NY
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.8 out of 10, Exceptional, (11 reviews)
"Quiet and lovely for a solo adventure with my dog. "
United States
Darcie B.
The price is SAR 676
SAR 1,182 total
includes taxes & fees
20 Jul - 21 Jul
Tiny Home, King Bed & Hot Tub, Unit B
Cottage (2 Bedrooms) | Interior

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 SAR 796
SAR 1,940 total
includes taxes & fees
6 Aug - 7 Aug
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
9.8 out of 10, Exceptional, (19 reviews)
"Amazing space, amenities and view! A perfect winter getaway. "
United States
Lee E.
The price is SAR 719
SAR 1,131 total
includes taxes & fees
23 Jul - 24 Jul
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside 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

Best Western Monticello

Best Western Monticello

10/10 Excellent
"Just a great place to be"
Maxwell 2-night trip
Posted 6 hours ago
Best Western Monticello

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?

Private Mountain Creek Getaway!: This vacation home rental outside of Middletown is located on a river and has an outdoor pool, a fireplace, 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 hot tub.

How many vacation rentals are there in Middletown?

With 12 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. 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.