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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Middletown vacation rentals

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

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.0 out of 10, (8 reviews)
"It was a great place "
United States
Jose
$168 nightly
The price is $190
Aug 3 - Aug 4
Total with taxes and fees
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.
$337 nightly
The price is $381
Jul 22 - Jul 23
Total with taxes and fees
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.
$199 nightly
The price is $224
Jul 29 - Jul 30
Total with taxes and fees
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)
$279 nightly
The price is $291
Jul 30 - Jul 31
Total with taxes and fees
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
$177 nightly
The price is $199
Jul 22 - Jul 23
Total with taxes and fees
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.
$108 nightly
The price is $120
Jul 22 - Jul 23
Total with taxes and fees
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)
"Clean and quiet."
United States
Ted
$169 nightly
The price is $172
Jul 22 - Jul 23
Total with taxes and fees
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.
$148 nightly
The price is $167
Jul 27 - Jul 28
Total with taxes and fees
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.
$207 nightly
The price is $234
Jul 23 - Jul 24
Total with taxes and fees
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.
$210 nightly
The price is $237
Jul 29 - Jul 30
Total with taxes and fees
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.
$291 nightly
The price is $332
Jul 22 - Jul 23
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Beach

Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (40 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
$225 nightly
The price is $252
Aug 3 - Aug 4
Total with taxes and fees
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.
$199 nightly
The price is $223
Jul 22 - Jul 23
Total with taxes and fees
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
$482 nightly
The price is $594
Jul 30 - Jul 31
Total with taxes and fees
Hay Loft Apartment in Barn - Goshen
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (11 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
$214 nightly
The price is $239
Jul 22 - Jul 23
Total with taxes and fees
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.
$255 nightly
The price is $288
Jul 26 - Jul 27
Total with taxes and fees
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
$475 nightly
The price is $585
Jul 27 - Jul 28
Total with taxes and fees
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.
$265 nightly
The price is $297
Jul 22 - Jul 23
Total with taxes and fees
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
$457 nightly
The price is $517
Aug 6 - Aug 7
Total with taxes and fees
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)
"Clean, comfortable cabin near New Paltz. Great views, well stocked kitchen."
United States
Heather G.
$327 nightly
The price is $332
Jul 26 - Jul 27
Total with taxes and fees
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Room was neat and clean. Breakfast was good. Overall my stay at this hotel was great."
Kathleen 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

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 $197 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?

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.