Beautiful Autumn View in Bear Mountain State Park

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middletown vacation rentals

Suite

1. 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
$138 nightly
The price is $156
Sep 8 - Sep 9
Total with taxes and fees
Cottage Suites
Interior

2. 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.
$372 nightly
The price is $421
Sep 6 - Sep 7
Total with taxes and fees
Hello Small Stone
Room

3. 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.
$172 nightly
The price is $193
Sep 23 - Sep 24
Total with taxes and fees
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Living area

4. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$285 nightly
The price is $297
Sep 4 - Sep 5
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Interior

5. 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
8.8 out of 10, Excellent, (20 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
$131 nightly
The price is $148
Sep 8 - Sep 9
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room

6. 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, (46 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.
$216 nightly
The price is $244
Aug 24 - Aug 25
Total with taxes and fees
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Interior

7. Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (116 reviews)
"Was very pet friendly. "
United States
Kevin
$211 nightly
The price is $237
Aug 27 - Aug 28
Total with taxes and fees
Trails Head Cabin
Interior

8. 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.
$111 nightly
The price is $125
Aug 25 - Aug 26
Total with taxes and fees
Trails Head Tiny House
Exterior

9. 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.
$191 nightly
The price is $216
Sep 1 - Sep 2
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
Room

10. Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Wurtsboro
9.0 out of 10, Wonderful, (2 reviews)
"The host was very welcoming and very responsive. The apartment was very cute and super clean. I came up for a Halloween event put on by a friend the location was very convenient in the downtown area and I could walk to most of the places I needed to get to I very much enjoyed my stay here and would stay again if I’m in the area. "
United States
Sheena C.
$246 nightly
The price is $276
Aug 31 - Sep 1
Total with taxes and fees
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Interior

11. 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, (31 reviews)
"Wonderful property will definitely book again."
United States
Jane G.
$174 nightly
The price is $176
Sep 7 - Sep 8
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Design Apartment, Patio, Garden View | View from room

12. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
$297 nightly
The price is $365
Aug 26 - Aug 27
Total with taxes and fees
Historic Horse Barn Apartment in Goshen
Property grounds

13. 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, (94 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
$206 nightly
The price is $230
Aug 27 - Aug 28
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
House (1 Bedroom) | Front of property

14. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
$364 nightly
The price is $412
Aug 24 - Aug 25
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
Private kitchen

15. 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.
$280 nightly
The price is $320
Aug 31 - Sep 1
Total with taxes and fees
Modern Hudson Valley Apt 202 - King/Queen/Twin
Beach

16. 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
$228 nightly
The price is $256
Aug 25 - Aug 26
Total with taxes and fees
Beaver Lake Escape
Outdoor spa tub

17. 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, (65 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
$522 nightly
The price is $546
Aug 26 - Aug 27
Total with taxes and fees
Country House w/Hot Tub, Deck, Grill & Fire Pit
Private kitchen

18. 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, (37 reviews)
"Great place, close to everything in Warwick, would stay again"
United States
Chris K.
$257 nightly
The price is $290
Aug 26 - Aug 27
Total with taxes and fees
The Wine House, Sitting atop of Warwick's brand new Wine Bar
Property grounds

19. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (17 reviews)
"Just what we were looking for"
United States
Natalya
$213 nightly
The price is $238
Sep 14 - Sep 15
Total with taxes and fees
TRANQUIL MOUNTAIN SOLITUDE
Property grounds

20. Rare River Views & Access, Cabin by Eden Islands

Rare River Views & Access, Cabin by Eden Islands
Montague
9.2 out of 10, Wonderful, (15 reviews)
"Host was accessible and very nice location to enjoy what nature brings."
United Kingdom
Rohan L.
$157 nightly
The price is $175
Aug 24 - Aug 25
Total with taxes and fees
Rare River Views & Access, Cabin by Eden Islands
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
"The staff made my day. They all display true hospitality and made each day better. Thank you so much."
Tiffany 3-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 $186 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?

Red Barn Retreat - Shawangunk Mountains Getaway: This vacation home rental outside of Middletown is located on a river and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the hot tub in this rental home to help you unwind.

How many vacation rentals are there in Middletown?

With 10 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.