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Middletown Holiday Rentals

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Check prices for these dates

Tonight
2 Aug - 3 Aug
Tomorrow
3 Aug - 4 Aug
Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 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
Exterior

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$1,307
HK$3,352 total
includes taxes & fees
3 Aug - 4 Aug
Hello Small Stone
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
6 bedrooms, desk, iron/ironing board, free WiFi

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!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

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$1,570
HK$2,478 total
includes taxes & fees
25 Aug - 26 Aug
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

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 HK$3,524
HK$4,729 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Property grounds

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$2,542 total
includes taxes & fees
5 Aug - 6 Aug
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

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 HK$2,437
HK$5,173 total
includes taxes & fees
3 Aug - 4 Aug
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour
Property grounds

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

10.0 out of 10, Exceptional, (43)
"Great Location and responsive owner. Thank you"
The price is HK$855
HK$2,098 total
includes taxes & fees
3 Aug - 4 Aug
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour
Cozy Cottage with Woodstock Scavenger Hunt
Property grounds

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 HK$1,091
HK$2,180 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Cottage with Woodstock Scavenger Hunt
Trails Head Tiny House
Exterior

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
4 Aug - 5 Aug
Trails Head Tiny House
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Property grounds

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$1,260
HK$2,461 total
includes taxes & fees
6 Aug - 7 Aug
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Interior

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!
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, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Fridge, microwave, oven, stovetop

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 HK$3,140
HK$4,645 total
includes taxes & fees
3 Aug - 4 Aug
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Lazy River Cottage on the Delaware River
Fireplace, books, music library, stereo

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

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

9.6 out of 10, Exceptional, (34)
"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
Terrace/patio

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 "
The price is HK$1,696
HK$3,382 total
includes taxes & fees
10 Aug - 11 Aug
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Romantic spot above restaurant., ideal for the gourmet
Exterior

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$1,177
HK$1,527 total
includes taxes & fees
4 Aug - 5 Aug
Romantic spot above restaurant., ideal for the gourmet
Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland
Fridge, microwave, oven, stovetop

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
Charming 2-bedroom cottage in delightful Eldred with WiFi
Outdoor pool

Charming 2-bedroom cottage in delightful Eldred with WiFi

10.0 out of 10, Exceptional, (1)
"This was a lovely little cottage on a shared property in a remote wooded area. The amenities (pool, fireplace, and trampoline) were great hits with my kids and the setting in the woods was stunning. The hosts were exceedingly gracious and kind. That said just note that the property is shared so you are utilizing the grounds of the host. "
Charming 2-bedroom cottage in delightful Eldred with WiFi
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

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

10/10 Excellent
"We had a wonderful stay. Dining options and shopping were no more than 10 minutes in either direction. Diner across the way serves good food too. Pool was clean. Breakfast was hot. Beds were comfortable. Can’t ask for more. "
Jeanne 2-night trip
Posted 1 day ago
Hampton Inn by Hilton Middletown

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?

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

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.