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Middletown Holiday Rentals

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Check prices for these dates

Tonight
11 Aug - 12 Aug
Tomorrow
12 Aug - 13 Aug
This weekend
15 Aug - 17 Aug
Next weekend
22 Aug - 24 Aug

Holiday Rentals in Middletown

Cottage Suites
Private kitchen

Cottage Suites

3.0 star property
6.6 out of 10, (7)
"It was a great place "
Cottage Suites
Hello Small Stone
Escape to a cozy cabin surrounded by a forested landscape, featuring a porch, deck, and garden area.

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!
Relax in a spacious room with a large bed, floor-to-ceiling windows, and a comfortable seating area.

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
Relax on the serene deck, surrounded by bare trees and a frozen lake.

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
Welcome to Minerals Resort & Spa, where guests can enjoy easy access to parking, hotel registration, and the Elements Spa.

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
Relax in a hot tub with a serene lake and forest view.

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
Fridge, microwave, oven, stovetop

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
Steps lead up to a cozy porch with a door in the center.

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
Relax by the fire pit surrounded by Adirondack chairs on this serene patio.

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
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

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.
Step out onto the deck and enjoy the serene surroundings.

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
Terrace/patio

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
Enjoy riverside camping with a portable grill, firewood, and scenic views.

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
Situated in a wooded area, this cabin offers a tranquil retreat with a spacious deck and a large glass door leading to the interior.

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
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

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!
Enjoy a serene view of the well-maintained lawn and trees from this room's large window.

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
Enjoy cooking in this well-equipped kitchen with oven, stovetop, and sink.

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
Enjoy a scenic view of the wooded area and body of water from the large window in this room.

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
Westtown Farm Restaurant & Bar offers a welcoming atmosphere with a porch and lush greenery.

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
Relax in this inviting living space with a floral-patterned sofa, wooden coffee table, and a dining area.

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.
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Top Middletown Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Breakfast items not available after 9am. "
Mohammad A 1-night trip
Posted 2 hours ago
Sleep Inn & Suites Middletown - Goshen

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.