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Compare 555 Vacation Homes in Middletown with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (17)
"The house comfortably slept the six of us."
Catskills mountain gateway house.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (3)
"we enjoyed our stay at Billy Moes bungalow. The property owner was very responsive and receptive to a couple minor issues we had and is working on correcting them. The wood burning fireplace is very easy to use and the owner provided supplies to get it started. I would definitely recommend this place to others. "
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Sun Drenched Lakefront Cove

9.2 out of 10, Wonderful, (16)
"THIS PLACE IS BEAUTIFUL AND SO CLEAN. MOST OF ALL VERY ROOMY NO ONE WAS ONE TOP OF EACH OTHER. AREA WAS SO PEACEFUL. THE ONLT THING I LEFT MY GLASSES BEHIND. BUT OTHER THEN THAT WE LOVED IT. "
Sun Drenched Lakefront Cove

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (48)
"This is an adorable cottage. It is very clean and well appointed. The kids (and adults) really enjoyed the detached game room. The hot tub and fire pit made for very relaxing evenings. We really enjoyed our time here. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (38)
"We had a great time and really enjoyed the area! Place was very clean, had everything we needed and the hot tub was great! "
Red Barn Retreat - Shawangunk Mountains Getaway

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (14)
"Nice location. Clean and comfortable. Was very cold inside when we entered (52 degrees) and I could not find an extra blanket anywhere. Everything else was great. "
Bright Cornwall-On-Hudson Vacation Rental!

Spacious Westtown Home, Firepit, Up to 10 Guest

10.0 out of 10, Exceptional, (4)
"I stayed for business and this was perfectly located for what I needed to get done in the area. "
Spacious Westtown Home, Firepit, Up to 10 Guest

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (287)
"The property is beautiful. It was cold when we were there, so we weren't able to take advantage of the outdoor amenities. The owner was very kind and communicated at a high level. I would highly recommend this property."
The price is SAR 1,460
SAR 1,960 total
includes taxes & fees
15 Apr - 16 Apr
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

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

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

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

2.0 star property
9.0 out of 10, Wonderful, (6)
"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

Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

2.0 star property
9.4 out of 10, Exceptional, (3)
"This home was newly renovated and very clean. Would stay there again."
The price is SAR 1,201
SAR 1,704 total
includes taxes & fees
21 Apr - 22 Apr
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (129)
"We were looking for a weekend in on the lake to relax and unwind and we got exactly that. The house was beautiful, clean and well maintained. Cheryl was attentive and came to help when needed. The views of the lake were breathtaking. Couldn’t have picked a better place. We can’t wait to come back! Thank you! "
Lakefront Luxury on Greenwood Lake

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

9.8 out of 10, Exceptional, (50)
"Our family had a truly wonderful winter holiday stay - our kids (3 and 5) loved having the books and toys available to use. The location was super convenient to hiking, snow tubing and indoor playareas. House was clean and the beds were very comfortable - we slept great especially after using the hot tub!"
The price is SAR 1,032
SAR 1,992 total
includes taxes & fees
15 Apr - 16 Apr
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Beaver Lake Escape

9.4 out of 10, Exceptional, (15)
"Greatly enjoyed our short stay. The dog bones were a nice touch for our pups. Extremely clean, great layout - we would love to return soon"
The price is SAR 582
SAR 971 total
includes taxes & fees
15 Apr - 16 Apr
Beaver Lake Escape

Modern Farmhouse on pristine private 12 Acres

9.6 out of 10, Exceptional, (76)
"We had a perfect stay at the beautiful farmhouse with all of the modern amenities.Outdoor space is to die for fenced in for your pup walking trails nature trails water features running streams..Cherry on top is that the listing is very generous with check-in and checkout times you can check in at 3 and you check out at 12. This feature allows for true relaxation!Book it!!"
Modern Farmhouse on pristine private 12 Acres

Dream House in the Gunks

10.0 out of 10, Exceptional, (25)
"This is my first time renting a property. Everything was "
The price is SAR 370
SAR 751 total
includes taxes & fees
1 May - 2 May
Dream House in the Gunks

Cozy Rustic Farmhouse With Wood Stove

Cozy Rustic Farmhouse With Wood Stove
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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Other property types in Middletown

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

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is SAR 631
SAR 1,053 total
includes taxes & fees
15 Apr - 16 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

9.8 out of 10, Exceptional, (59)
"2nd visit. Loved being able to use the fireplace this time!"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
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.