Photo by Vincent Ramundo

Middletown Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday 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 HK$1,272
HK$3,277 total
includes taxes & fees
13 Aug - 14 Aug
Hello Small Stone

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

9.0 out of 10, Wonderful, (78)
"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!

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

10.0 out of 10, Exceptional, (302)
"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 HK$3,525
HK$4,664 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

10.0 out of 10, Exceptional, (45)
"Excelente place to stay and the host was very attentive.Will definitely be back "
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (17)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is HK$2,296
HK$4,977 total
includes taxes & fees
13 Aug - 14 Aug
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very good, (1)
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Trails Head Tiny House

9.2 out of 10, Wonderful, (17)
"A lovely tiny house, great hosts "
The price is HK$629
HK$1,057 total
includes taxes & fees
17 Aug - 18 Aug
Trails Head Tiny House

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

10.0 out of 10, Exceptional, (62)
"Beautiful views!"
The price is HK$1,111
HK$2,290 total
includes taxes & fees
12 Aug - 13 Aug
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

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

2.0 star property
9.8 out of 10, Exceptional, (12)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is HK$3,140
HK$4,645 total
includes taxes & fees
12 Aug - 13 Aug
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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 HK$1,413
HK$2,576 total
includes taxes & fees
12 Aug - 13 Aug
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

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

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

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

9.6 out of 10, Exceptional, (36)
"It is perfectly located by the river. Breathe taking views"
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (29)
"Very nice cabin that is nicely keep with everything you need. I will be hoping to visit again "
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

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 HK$1,594
HK$2,522 total
includes taxes & fees
25 Aug - 26 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

9.6 out of 10, Exceptional, (46)
"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!

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

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (156)
"Everything was amazing. We spent Thanksgiving here. We definitely come back!"
Lazy River Cottage on the Delaware River

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (2)
"Highly recommended! Such a vibe, quiet & cozy. You can hear the birds in the morning, so peaceful. I would go back!! "
The price is HK$1,178
HK$1,519 total
includes taxes & fees
12 Aug - 13 Aug
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, (36)
"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 HK$1,127
HK$2,351 total
includes taxes & fees
18 Aug - 19 Aug
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals in Middletown close to Orange County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Middletown has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Middletown is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

With 12 Expedia holiday rentals, you're guaranteed 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 such as LEGOLAND® New York and Woodbury Common Premium Outlets.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.