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Browse Select Middletown Vacation Homes

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

10.0 out of 10, Exceptional, (301)
"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 CA $556
CA $741 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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 CA $427
CA $907 total
includes taxes & fees
Aug 13 - Aug 14
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 CA $549
CA $813 total
includes taxes & fees
Sep 2 - Sep 3
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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

6.0 out of 10, (1)
"Although the original check-in process was fine, the host became unresponsive to our questions during the stay. We were able to figure out the answers to our questions, but it would have been nice to hear anything at all. We went so far as to text the host because we became concerned after radio silence for 3 days. Once she did respond she didn't apologize for not getting back to us and ghosting us for days. "
The price is CA $166
CA $262 total
includes taxes & fees
Aug 13 - Aug 14
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (50)
"The property is close to Minawaska State Park where we went hiking. We enjoyed the hot tub and had a nice stay. There are a number of nice restaurants nearby too."
Red Barn Retreat - Shawangunk Mountains Getaway

Play, Swim & Unwind: Family Home in Glen Wild!

8.0 out of 10, Very good, (1)
"Had an issue with the Internet when we arrived. The maintenance people cut the cable coming into the house when they were cutting the grass. It was hard to work while I was there as I expected to have Internet access. Eventually it was fixed but it took a few days. Aside from this the house was pleasant and the kids loved the pool and basketball court. "
Play, Swim & Unwind: Family Home in Glen Wild!

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!

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

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

10.0 out of 10, Exceptional, (1)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
The price is CA $129
CA $221 total
includes taxes & fees
Sep 2 - Sep 3
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

The Warwick Inn Boutique Amity Room 3 an Hour from NYC

8.6 out of 10, Excellent, (4)
"Was happy with the room, nice property easy to walk to main street. Would stay there again."
The price is CA $152
CA $247 total
includes taxes & fees
Aug 10 - Aug 11
The Warwick Inn Boutique Amity Room 3 an Hour from NYC

Dog friendly private 3-bedroom house bordering the Mohonk Preserve

10.0 out of 10, Exceptional, (7)
Dog friendly private 3-bedroom house bordering the Mohonk Preserve

Trails Head Tiny House

9.2 out of 10, Wonderful, (17)
"A lovely tiny house, great hosts "
The price is CA $110
CA $185 total
includes taxes & fees
Aug 10 - Aug 11
Trails Head Tiny House

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 CA $248
CA $451 total
includes taxes & fees
Aug 12 - Aug 13
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)
"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 CA $198
CA $412 total
includes taxes & fees
Aug 18 - Aug 19
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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

The price is CA $291
CA $722 total
includes taxes & fees
Aug 12 - Aug 13
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The Woodbury Cottage

8.8 out of 10, Excellent, (23)
"Really enjoyed our stay at this comfy cottage. Easily slept a family of 3 with plenty of room to lounge around. It's an older cottage, but the owner has added a lot of neat touches that make this a nice place to stay in this area."
The Woodbury Cottage

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"Wonderful front porch "
Charming Highland Falls Home < 2 Mi to West Point!

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

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"We loved the new furniture and sheets and blankets. Everything was spotless and felt super comfortable and homey. Big space as well! "
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Amazing All-Season, Private Lakefront Retreat!

9.8 out of 10, Exceptional, (57)
"Had a wonderful time. The house was fantastic and the lake was enjoyable. Would definitely come back."
Amazing All-Season, Private Lakefront Retreat!
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