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Compare 465 Vacation Homes in Middletown with updated reviews, rates, and availability.

Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is $189
$375 total
includes taxes & fees
Jun 2 - Jun 3
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Exterior
4 bedroom Farmhouse, hot tub, secluded, near hiking, wineries, Bethel Woods
The price is $140
$390 total
includes taxes & fees
May 24 - May 25
4 bedroom Farmhouse, hot tub, secluded, near hiking, wineries, Bethel Woods
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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Living area
Beaver Lake Escape
10.0 out of 10, Exceptional, (2)
"This cottage is this perfect place for a quick little getaway! We had the most perfect lazy stay for the weekend secluded from the city. Just sitting outside the cottage watching the lake in silence was so peaceful. The host was also extremely responsive and detailed in her messages. Would highly recommend."
The price is $165
$257 total
includes taxes & fees
May 30 - May 31
Beaver Lake Escape
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.6 out of 10, Exceptional, (12)
"Great location and communication! Very clean and nice!"
The price is $159
$327 total
includes taxes & fees
May 27 - May 28
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Outdoor dining
Great hikes, Crystal Springs Spa, 1 block off the lake & Pet Friendly!
9.6 out of 10, Exceptional, (10)
"This cabin is fun and well-appointed. The kitchen had all the equipment we needed to cook, and the beds and other furniture were comfortable. The photos don't convey how pretty the lake is. Highly recommended."
Great hikes, Crystal Springs Spa, 1 block off the lake & Pet Friendly!
Fridge, microwave, oven, stovetop
Contemporary Cottage less than an hour from NYC!
10.0 out of 10, Exceptional, (16)
"Near our family in NJ. Close to the city, very quiet neighborhood."
Contemporary Cottage less than an hour from NYC!
Fridge, microwave, oven, stovetop
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
10.0 out of 10, Exceptional, (14)
"The host was fantastic with details and communication. Can’t wait to stay here again."
Modern Farmhouse; Quiet, Eclectic,Cozy, Fun, situated on a peaceful Creek.
Living area | Smart TV, fireplace
Catskills mountain gateway house.
9.6 out of 10, Exceptional, (7)
"Nice and quiet. Everything you need is provided. Sadly we had 2 rainy days, but we walked to the roosa gap fire tower with the kids on a nice morning! Great views from the back deck."
Catskills mountain gateway house.
Fridge, microwave, stovetop, dishwasher
Bright Cornwall-On-Hudson Vacation Rental!
10.0 out of 10, Exceptional, (3)
"Excellent location, well-equipped, comfortable and clean. Everything we hoped for!"
Bright Cornwall-On-Hudson Vacation Rental!
Property grounds
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (115)
"We spent a much needed relaxing weekend at this location. I can't say enough good things about this property. It was beautifully decorated, perfectly supplied, and very clean. We would rent this property again."
Lakefront Luxury on Greenwood Lake
Fridge, microwave, oven, stovetop
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
9.2 out of 10, Wonderful, (16)
"We thoroughly enjoyed ourselves at this sweet home, making great use of the spacious yard with the fire pit, the hot tub, and the grill. I kept being amazed at how easy everything was. Every time I needed a utensil, it was wherever I first looked! And when the propane tank emptied in the middle of grilling dinner, I glanced around to see where we might find a full one, and there was one right there waiting. I really appreciated how well thought out and organized everything was. And communication...
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Exterior
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
10.0 out of 10, Exceptional, (9)
"Had a great time at this house. It is perfect for large groups and had so many great amenities. Doug was extremely responsive and helpful. Highly recommend!"
Getaway w/ ALL- Pool, Hot Tub, Game Room, Dog Run, Playground, Near Mountains!
Outdoor dining
Black Walnut Tree Farm: Farmhouse on 50 Acres
10.0 out of 10, Exceptional, (13)
"Four friends had a wonderful time at Black Walnut Tree Farm. The space was amazing! There was plenty of spaces that we could hang out together, but also we each had areas that we could retreat to. The kitchen was well-stocked ands spacious, the large living room had many comfortable seats around the fire, and there was a great sunroom where we could sit and play games. The grounds were huge and one could easily get lost walking around the property. We all loved the place and are collectively...
Black Walnut Tree Farm: Farmhouse on 50 Acres
Microwave, oven, dishwasher
LOCATION ! This unique property is walking distance to the Village of Warwick!
10.0 out of 10, Exceptional, (3)
"This was the best stay we have had in the over 35 years of going back to NY to visit family. Was such a refreshing change to be able to have family and friends come to our place to visit. The Host couldn't have been nicer in working with us as we were first time Vrbo users and made a few mistakes. The house was wonderful, and they had everything they promised and more. Thanks for making our visit the best ever."
LOCATION ! This unique property is walking distance to the Village of Warwick!
Property grounds
12 Private Acres with pristine Views of the Gunks
9.6 out of 10, Exceptional, (69)
"This home has been updated nicely and is situated on a nice amount of land to take your pup for a nice walk during the mornings and whenever you are "at home." The kitchen has been well renovated and the beds are very comfy. Close to lots of good hiking and food in New Paltz and the surrounding area. Simone is a responsive host."
12 Private Acres with pristine Views of the Gunks
Smart TV, fireplace, video games, table tennis
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
10.0 out of 10, Exceptional, (4)
"Great spot, super attentive property managers, house had everything we needed and more!"
The price is $527
$916 total
includes taxes & fees
May 28 - May 29
Dream escape, new modern farmhouse, stunning views, game room & hot tub for 10+!
Pool
Secluded lakefront home With an EV charger
10.0 out of 10, Exceptional, (6)
"This house was perfect for family weekend getaway. Was secluded and right on the brrok that feeds the lake."
Secluded lakefront home With an EV charger
Don't see what you're looking for?
See all available properties in Middletown
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.

Other property types in Middletown

Luxury Studio | Private kitchen | Full-size fridge, microwave, oven, stovetop
Cottage Suites
3.0 star property
The price is $132
$257 total
includes taxes & fees
May 27 - May 28
Cottage Suites
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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.

Middletown Vacation Homes information

Number of reviews
345
Accommodation
465 Vacation Homes
Lowest Price
$140
Highest Price
$527

Recent reviews of Middletown hotels
Expedia verified reviews

Tru by Hilton Middletown

Tru by Hilton Middletown

5/5 Excellent
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A verified traveler stayed at Tru by Hilton Middletown
Posted 1 day ago
Tru by Hilton Middletown