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Compare 464 Vacation Homes in Middletown with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (42)
"The perfect spot for a Beacon/Newburgh getaway! Great access to the towns, Storm King State Park, and Storm King Art Center! Lovely house, great game room (played so much ping pong and darts), and the hot tub was perfect."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

The Perfect up to date Private Getaway to call home for a while

8.6 out of 10, Excellent, (4)
"This property and listing was perfect for our men's retreat weekend getaway. We gathered together and enjoyed being able to spread out in the spacious home. It was very close to a local park with a pool, basketball court, and open field. We also enjoyed grilling on the patio and using the fire-pit to roast s'mores in the evening. The driveway had plenty of parking. The pool on the property was unusable but the backyard was perfect for us to play football and have outdoor activities. We...
The Perfect up to date Private Getaway to call home for a while

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

Elegant and spacious home with sauna and heated pool

Elegant and spacious home with sauna and heated pool

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

9.6 out of 10, Exceptional, (21)
"Enjoyed the accommodation and all tge area had to offer. We did the Sky ride and Coaster So Great. Went to Warwick Apple Festival Awesomeness and Blue Arrow Farm for concert. Highly recommend "
The price is AED 586
AED 1,200 total
includes taxes & fees
6 Jan - 7 January 2025
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AED 540
AED 1,194 total
includes taxes & fees
13 Jan - 14 January 2025
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

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

9.4 out of 10, Exceptional, (30)
"Everything was good and we all enjoyed our stay"
The price is AED 1,117
AED 2,017 total
includes taxes & fees
14 Jan - 15 January 2025
Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

Spectacular ~10k sqft Mansion w/Pool&Tennis

10.0 out of 10, Exceptional, (4)
"this house was AMAZING and met every one of our needs and exceeded our expectations. we had 3 children and 19 adults and every person was comfortable. the kids area was perfect and we barely saw them. we already started talking about what we can do next to to have an excuse to stay in the houee again. "
The price is AED 7,346
AED 11,112 total
includes taxes & fees
25 Dec - 26 Dec
Spectacular ~10k sqft Mansion w/Pool&Tennis

By Mtn Creek Resort: ‘The Point on Highland Lake’

9.8 out of 10, Exceptional, (60)
"The Point was an excellent choice for our family, plenty of room and things to do for everyone. Please was very well equipped and very clean. The lake area and surrounding area was a great location for us. Highly recommended."
By Mtn Creek Resort: ‘The Point on Highland Lake’

Luxury Lakeside Paradise

9.6 out of 10, Exceptional, (4)
"Our family stayed for a number of days in Chaya's wonderful house on Swinging Bridges Lake. Everything about this house is great, and we would LOVE to come back! Thank you Chaya for being a gracious and attentive hostess!"
Luxury Lakeside Paradise

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!

The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds

2.0 star property
The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming 3-bedroom Newly Renovated house in Highland Falls with AC, WiFi

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Riverfront modern house with beautiful views

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is AED 1,088
AED 1,728 total
includes taxes & fees
9 Jan - 10 January 2025
Riverfront modern house with beautiful views

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Trails Head Tiny House

9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AED 290
AED 455 total
includes taxes & fees
23 Dec - 24 Dec
Trails Head Tiny House

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (12)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
The price is AED 2,777
AED 4,615 total
includes taxes & fees
3 Jan - 4 January 2025
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Delightful Home w/ Fire Pit, Walk to Lake!

9.8 out of 10, Exceptional, (9)
"This was a cute house in a beautiful spot of NY. It was cozy and well taken care off. The neighborhood was quiet and beautiful also. We would come agian. "
Delightful Home w/ Fire Pit, Walk to Lake!

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (10)
"First time using Vrbo, and I was not disappointed! This property was comfortable, clean and well equipped. We were all very satisfied. "
Bright Cornwall-On-Hudson Vacation Rental!
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

Cottage Suites

3.0 star property
8.0 out of 10, Very Good, (3)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AED 617
AED 915 total
includes taxes & fees
28 Dec - 29 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Trails Head Tiny House

9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AED 290
AED 455 total
includes taxes & fees
23 Dec - 24 Dec
Trails Head Tiny House
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.