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Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

Our top choices for Middletown holiday homes

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

10.0 out of 10, Exceptional, (303)
"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 AU$941
includes taxes & fees
28 Aug - 29 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly

10.0 out of 10, Exceptional, (3)
"Awesome place. Cozy and great communication with owners. "
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly

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

9.0 out of 10, Wonderful, (81)
"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

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 AU$498
includes taxes & fees
1 Sept - 2 Sept
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

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

9.4 out of 10, Exceptional, (36)
"Nice and clean"
The price is AU$477
includes taxes & fees
25 Aug - 26 Aug
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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 AU$892
includes taxes & fees
15 Sept - 16 Sept
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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 AU$803
includes taxes & fees
22 Sept - 23 Sept
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (7)
"The location is close to legoland which is nice. They had connect 4 and some playing cards otherwise the property isnt great for little ones due to some odd decor choices. There were ants and a spider and unsure about the cleaning. Thermostat didnt adjust and dishwasher didnt work. Tvs were hard to use. Wish there had been printed instructions for where to find things in the house, as well as recommendations in the town. Didnt use outdoor deck because too cold but also couldnt open the door and...
Stylish & Peaceful Getaway on 3 Private Acres

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is AU$964
includes taxes & fees
1 Sept - 2 Sept
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

7.0 out of 10, Good, (2)
"Nice to have top notch bar/restaurant downstairs!"
The price is AU$251
includes taxes & fees
15 Sept - 16 Sept
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Nature Getaway ~ Creek, Firepit, Deck, Privacy

2.5 star property
10.0 out of 10, Exceptional, (2)
"We enjoyed our nature getaway! Kids enjoyed playing in the yard and the creek right on the property. "
Nature Getaway ~ Creek, Firepit, Deck, Privacy

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (22)
"Property was perfect for our needs."
Bright Cornwall-On-Hudson Vacation Rental!

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

9.8 out of 10, Exceptional, (11)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cozy property with privacy and comfort. "
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

★Forest and River Side Tranquil House★

8.6 out of 10, Excellent, (9)
"No complaints for our one night stay. Cute house inside and very clean!"
The price is AU$384
includes taxes & fees
25 Aug - 26 Aug
★Forest and River Side Tranquil House★

Home bordering the Mohonk Preserve, Dog friendly, private 3-bedroom

10.0 out of 10, Exceptional, (10)
Home bordering the Mohonk Preserve, Dog friendly, private 3-bedroom

Lavender Hill Estate, Private 37 acres,1.5 hour from NYC, Heated Pool, Jacuzzi,

10.0 out of 10, Exceptional, (52)
"This was our third visit with family (6 adults, two children) and again it was a wonderful experience. Pool, hot tub, beautiful property, everything delightful."
Lavender Hill Estate, Private 37 acres,1.5 hour from NYC, Heated Pool, Jacuzzi,

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.4 out of 10, Exceptional, (8)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (53)
"The property was beautiful, our host, accommodating. Everything was wonderful, and we were sad to leave."
Red Barn Retreat - Shawangunk Mountains Getaway
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