Middletown Vacation Rentals from ￥10,387: Search Short-Term Rentals

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Vacation Rentals in Middletown

"Great place and host!"

￥44,622 total

includes taxes & fees

Jun 23 - Jun 24

"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."

5 bedrooms, desk, iron/ironing board, free WiFi

"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."

"Everything was amazing. We spent Thanksgiving here. We definitely come back!"

"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "

￥77,330 total

includes taxes & fees

Jun 23 - Jun 24

"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."

￥31,468 total

includes taxes & fees

Jun 25 - Jun 26

Fridge, oven, stovetop, coffee/tea maker

"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. "

"A lovely tiny house, great hosts "

￥18,194 total

includes taxes & fees

Jun 23 - Jun 24

"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. "

￥44,474 total

includes taxes & fees

Jun 24 - Jun 25

"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "

"Wonderful stay!"

￥78,254 total

includes taxes & fees

Jun 23 - Jun 24

"Excellent "

"Nicely located near lots of beautiful hiking trails. Quiet at night and quite comfortable."

"Wish we could have stayed longer. Great place and lots of room for your whole family. "

￥61,816 total

includes taxes & fees

Jun 29 - Jun 30

"Really liked that each room had it's own temperature control"

"The place was absolutely beautiful. Want to come back again very soon"

"We had a great time staying here. It was a little too cold to really enjoy the hot tub but the house was nice and we love the area. Definitely check out Forage Pizza about 20 minutes away."

"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "

￥22,171 total

includes taxes & fees

Jun 23 - Jun 24

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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!

Recent reviews of Middletown properties

5/5 Excellent

"I appreciated the fire pit outdoors for after hours. When we returned from the wedding nearby, we were able to continue to spend together at the hotel. Ice was on hand and check-in was friendly and easy. "

A verified traveler stayed at Courtyard by Marriott Middletown Goshen

Posted 1 day ago

Fairfield Inn & Suites by Marriott Goshen Middletown

5/5 Excellent

"Only about five minutes to the entrance of Legoland, this is a convenient area for a cost-effective night stay. It’s no frills, but it’s clean and the breakfast is decent. A good value for the money."

A verified traveler stayed at Fairfield Inn & Suites by Marriott Goshen Middletown

Posted 1 day ago

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 13 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.

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Middletown Vacation Rentals

Check prices for these dates

Vacation Rentals in Middletown

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8

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

Lazy River Cottage on the Delaware River

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

Trails Head Cabin

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

Trails Head Tiny House

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

Spacious Getaway! 7BR w Park & pool Scenic Views

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

Modern penthouse suite in a restored grain tower with private roof deck.

Cozy Cabin with Sauna & Firepit!

Bethel Woods Cabin with River

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Vernon Condo w/ Deck, Near Appalachian Trail!

Cozy Bethel Cabin Retreat with Private Hot Tub

Glamping Tent & Campsite by Minnewaska State Park

The retreat at Poconos Mansion | 50 guests | private

Find out more about Middletown

Recent reviews of Middletown properties

Courtyard by Marriott Middletown Goshen

Hampton Inn Harriman Woodbury

Fairfield Inn & Suites by Marriott Goshen Middletown

Resorts World Catskills Casino

The Crossroads Hotel, Newburgh

The Kartrite Resort & Indoor Waterpark

Sleep Inn & Suites Middletown - Goshen

Hampton Inn by Hilton Middletown

Overlook Lodge at Bear Mountain

Frequently asked questions