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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Cottage Suites

3.0 star property
6.6 out of 10, (7)
"It was a great place "
Cottage Suites

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house was great. It was nice to sit and relax by the small pond in the back."
The price is CA $230
CA $591 total
includes taxes & fees
Aug 3 - Aug 4
Hello Small Stone

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is CA $282
CA $455 total
includes taxes & fees
Aug 4 - Aug 5
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (300)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is CA $559
CA $745 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

10.0 out of 10, Exceptional, (4)
"Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! "
The price is CA $249
CA $448 total
includes taxes & fees
Aug 5 - Aug 6
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

10.0 out of 10, Exceptional, (43)
"Great Location and responsive owner. Thank you"
The price is CA $151
CA $370 total
includes taxes & fees
Aug 3 - Aug 4
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (75)
"We had an amazing stay at this property! Everything was exactly as described—clean, comfortable, and beautifully maintained. It felt like a true home away from home. The location was perfect, and all the amenities were thoughtfully provided.What really stood out was how smooth and stress-free the whole process was. Communication with the owner was excellent from start to finish—quick responses, clear instructions, and super helpful throughout. It made the entire experience even better.Highly...
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

10.0 out of 10, Exceptional, (62)
"Beautiful views!"
The price is CA $234
CA $448 total
includes taxes & fees
Aug 6 - Aug 7
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is CA $461
CA $951 total
includes taxes & fees
Aug 3 - Aug 4
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Trails Head Cabin

9.8 out of 10, Exceptional, (87)
"The Trails Head Cabin was a wonderful getaway for the weekend! It was very clean and nestled in a great area. We enjoyed exploring the trails right next door as well as going up the road for dinner and drinks at Brew."
The price is CA $174
CA $308 total
includes taxes & fees
Aug 4 - Aug 5
Trails Head Cabin

Cozy Cottage with Woodstock Scavenger Hunt

10.0 out of 10, Exceptional, (2)
"this spot was exactly what we needed for an overnight in the area. clean, easy to find, excellent communication and exactly as picturedsaving this for future needs for sure "
The price is CA $192
CA $384 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Cottage with Woodstock Scavenger Hunt

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Trails Head Tiny House

9.2 out of 10, Wonderful, (17)
"A lovely tiny house, great hosts "
The price is CA $111
CA $186 total
includes taxes & fees
Aug 4 - Aug 5
Trails Head Tiny House

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (11)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is CA $622
CA $898 total
includes taxes & fees
Aug 3 - Aug 4
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (154)
"Gorgeous location to unplug and connect with nature. Serene setting. Clean and charming. Host was lovely and responsive. Highly recommend. "
Lazy River Cottage on the Delaware River

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (45)
"Love the hot tub, love the location Absolutely loved our stay! The place was clean, cozy, and exactly as described. Great location, easy check-in, and the host was super responsive."
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

8.8 out of 10, Excellent, (5)
The price is CA $106
CA $206 total
includes taxes & fees
Aug 3 - Aug 4
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (1)
"Highly recommended! Such a vibe, quiet & cozy. You can hear the birds in the morning, so peaceful. I would go back!! "
The price is CA $207
CA $268 total
includes taxes & fees
Aug 3 - Aug 4
Romantic spot above restaurant., ideal for the gourmet

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

9.4 out of 10, Exceptional, (32)
"Really great place for an overnight trip to Mountain Creek. Plenty of space for 2 adults, great location and access to the amenities after a long day month slopes was a total bonus. Great communication, easy access and parking. "
The price is CA $199
CA $421 total
includes taxes & fees
Aug 4 - Aug 5
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very big and spacious. We had a large group, yet everyone had more than enough room.Looking forward to renting this place again. "
Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland
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

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 Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This vacation home rental outside of Middletown is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.