Photo by Vincent Ramundo

Search Vacation Homes in Middletown

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 447 Vacation Homes in Middletown with updated reviews, rates, and availability.

Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (32)
"We had a great time staying in Gardiner, NY. The Red Barn Retreat was perfect! There are so many things to do near this location. We visited Hyde Park, had lunch at the Culinary Institute, hiked the Monhonk Preserve, explored Historic Huguenot Street, checked out New Paltz for the first time and did the Walkway Over the Hudson on the way home. I loved relaxing under the stars in the hot tub and just gazing out at the view. My spouse just asked me last night, "When are we going back?" Bill is a...
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]
9.6 out of 10, Exceptional, (4)
"Our family stayed here while visiting a nephew at West Point, around 35 min away. The house was very clean and check-in was flawless. The beds and pillows were comfortable. We spent a lot of time in the game room playing ping pong, air hockey, and pool. We did not swim in the pool but it looked amazing. A perfect place for us and we will definitely return if in the area again."
The price is AED 2,626
AED 4,068 total
includes taxes & fees
3 Dec - 4 Dec
complete privacy vacation home [private pool]
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is AED 1,485
AED 3,076 total
includes taxes & fees
25 Nov - 26 Nov
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
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 628
AED 1,300 total
includes taxes & fees
3 Dec - 4 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
8.8 out of 10, Excellent, (16)
"Close to the trails. Loved the park with the trails. "
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
Nature Getaway: Charming Villa Near Trails and Parks
7.2 out of 10, Good, (9)
"Really cool house. We has some issues with our stay. It took a bit to get in touch with the manager to resolve the issues. The next day the brought most if the items needed that the h"
Nature Getaway: Charming Villa Near Trails and Parks
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
9.4 out of 10, Exceptional, (3)
" This space was the perfect place to come back to after a day filled with fun fall activities. The property had everything we needed to cook a nice dinner. And there were ample entertainment provided options for the evening. The property was clean and spacious. It is a great place to stay, I would highly recommend it."
The price is AED 643
AED 1,025 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
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!
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
1 Dec - 2 Dec
Trails Head Tiny House
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
8.0 out of 10, Very Good, (5)
"The home was in a perfect spot with lake views and is nicely close to town. We picked the home for its closeness to the rein fair and I’m so glad we did, It was wonderfully quiet and relaxing after a long day of hanging out at the rein fair !"
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
9.2 out of 10, Wonderful, (22)
"This property was clean and exactly as described. We were in the area for a family gathering and it allowed us a quiet place to regroup with our dog at night. Highly recommend and are hoping to visit again. "
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Perfect for families and large groups
9.4 out of 10, Exceptional, (10)
"Nice house with plenty of room and very clean."
Perfect for families and large groups
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
9.8 out of 10, Exceptional, (114)
"Lakefront House on Greenwood Lake is awesome. We were in town to visit Watchtower Headquarters in Warwick. The house was clean and comfortable. Communication was Jody was quick. We enjoyed the lake so much! We look forward to returning again."
Lakefront House on Breathtaking Greenwood Lake, NY Short Term Rental 33118
5 Acre Modern Mountain Farm
9.4 out of 10, Exceptional, (28)
"We enjoyed our stay. The property is beautiful. Some extra bath towels would be nice. We would definitely stay again!"
The price is AED 1,006
AED 1,892 total
includes taxes & fees
9 Dec - 10 Dec
5 Acre Modern Mountain Farm
Private Mountain Creek Getaway!
8.0 out of 10, Very Good, (4)
"We enjoyed our stay. The place had all we needed. It was super close to Mountain Creek - Our last adventure for our daughters who had raced together for 6 years amd are now off to college!!! All communications were clear and Charlie responded quickly with any questions."
The price is AED 946
AED 1,921 total
includes taxes & fees
24 Nov - 25 Nov
Private Mountain Creek Getaway!
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
9.8 out of 10, Exceptional, (90)
"Very close to hiking and biking trails! Beds were comfortable "
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
Sweet and spacious mountain view home w/fireplace!
9.8 out of 10, Exceptional, (18)
"Loved the layout and the amount of natural light"
Sweet and spacious mountain view home w/fireplace!
Autumn Serenity in the Catskills nearby Delaware River Gap w/ Game Rm, Fireplace
9.6 out of 10, Exceptional, (20)
"I hosted a family dinner for my mom’s 60th birthday with a cozy fall menu. This house fit the theme well and we had plenty of space. Unfortunately we didn’t have time to use the fire pit but I’m sure that would have been lovely! Thank you for your hospitality! "
The price is AED 1,157
AED 2,105 total
includes taxes & fees
6 Dec - 7 Dec
Autumn Serenity in the Catskills nearby Delaware River Gap w/ Game Rm, Fireplace
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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in

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
Royal Garden Main Cabin
9.6 out of 10, Exceptional, (4)
"ABSOLUTELY BEAUTIFUL!!! Its was a treat staying here. Its out in the country. Its called a cabin but its more of a house. The bedrooms were perfect and the beds were comfy. The property had a pond, and a fire pit. We seen 3 deer as we were pulling into the driveway. ABSOLUTELY RECOMMEND THIS RENTAL!!"
Royal Garden Main Cabin
Lazy River Cottage on the Delaware River
10.0 out of 10, Exceptional, (130)
"We absolutely loved our stay at Lazy River Cottage! The cottage was clean, well-decorated, and full of light. The view of the river was stunning and such a delight to observe in the mornings. David was responsive to our needs. We highly recommend this property!"
Lazy River Cottage on the Delaware River
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.