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Vacation Homes in Middletown

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

9.0 out of 10, Wonderful, (84)
"Great property for a group trip. We enjoyed the house it was spacious and had everything we needed. The lake, kayaks and paddle boards were a lot of fun. I highly recommend and would stay again."
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, (9)
"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 AED 661
AED 1,201 total
includes taxes & fees
1 Oct - 2 Oct
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

9.8 out of 10, Exceptional, (15)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (23)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is AED 790
AED 1,907 total
includes taxes & fees
21 Oct - 22 Oct
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

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

10.0 out of 10, Exceptional, (308)
"We had the most relaxing 3 night stay at Don's vacation home. It is spacious and comfortable. Orange Lake right out the back door was a beautiful backdrop all throughout the day. Don gave us great recommendations for local restaurants too.It was the perfect weekend."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
The price is AED 1,488
AED 2,503 total
includes taxes & fees
30 Sep - 1 Oct
Large,Cozy,Bright Apartment, Business Themed.

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

9.4 out of 10, Exceptional, (38)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
The price is AED 526
AED 1,116 total
includes taxes & fees
3 Oct - 4 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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

9.8 out of 10, Exceptional, (12)
"We were very comfortable and enjoyed our stay. We enjoyed the deer and bunnies!"
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Mountain Peak Retreat - Pool - Hot Tub

10.0 out of 10, Exceptional, (5)
The price is AED 1,837
AED 3,645 total
includes taxes & fees
30 Sep - 1 Oct
Mountain Peak Retreat - Pool - Hot Tub

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

9.8 out of 10, Exceptional, (6)
"My family and I had a great time at this property. Located on a beautiful property. Very relaxing and coordinating with the property owner was very easy. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

9.4 out of 10, Exceptional, (39)
"Very nice location and spacious house.Bbq grill could be better"
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"Cozy property with privacy and comfort. "
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

Apple-Pumpkin Picking! Private 3-bedroom home bordering the Mohonk Preserve

10.0 out of 10, Exceptional, (12)
"We had an incredible stay! We came up for a ladies weekend to get outdoors, explore the area, and do some cooking in and this property was the perfect spot for all of the above. The layout was ideal with a bedroom on every level and the location was sublime, right next to the Mohonk Preserve! Owls, woodpeckers, snakes and birdsong were all lovely additions to our stay. We will certainly be back! "
Apple-Pumpkin Picking! Private 3-bedroom home bordering the Mohonk Preserve

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (22)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

Spacious 6BR Villa - Serene Scenic Mountain Escape

10.0 out of 10, Exceptional, (4)
"The house was fantastic as was the host. Our group had an amazing weekend together and I highly recommend"
Spacious 6BR Villa - Serene Scenic Mountain Escape

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

10.0 out of 10, Exceptional, (56)
"This property is STUNNING and the hosts are just lovely! The on-site amenities, nearby wineries, Angry Orchard Cider House, Gardiner (Wilflower Farms restaurant is to die for), New Paltz farmers market, and Gunks hiking are all incredible. Cannot recommend a stay here enough! "
Lavender Hill Estate, Private 37 acres,1.5 hour from NYC, Heated Pool, Jacuzzi,

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is AED 1,245
AED 1,851 total
includes taxes & fees
30 Sep - 1 Oct
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

9.8 out of 10, Exceptional, (86)
"Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back...
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (35)
"We had a peaceful stay here while we were in town for a few days.The cabin was very cute, clean, and the neighborhood/ neighbors were very quiet. The steps into the bathroom and bedroom were illuminated and the upstairs loft was a cool getaway for our teenager.Recommend taking a bigger vehicle that can take a rough gravel road."
Cozy Cabin with Sauna & Firepit!

Catskills Getaway: 3BR Retreat w/ Media Room, Near Casino, Bethel Woods & More!

10.0 out of 10, Exceptional, (2)
"We had a wonderful experience in this beautiful home! We enjoyed grilling and sitting by the campfire, as well as the charm of this well decorated home. We will be recommending and coming back !"
The price is AED 808
AED 1,259 total
includes taxes & fees
30 Sep - 1 Oct
Catskills Getaway: 3BR Retreat w/ Media Room, Near Casino, Bethel Woods & More!
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