A large steel bridge spanning a river, surrounded by trees and buildings.

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Our top choices for Middletown cottages

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is ¥23,512
¥63,996 total
includes taxes & fees
Jun 22 - Jun 23
Hello Small Stone

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is ¥29,518
¥83,057 total
includes taxes & fees
Jun 28 - Jun 29
Hudson Valley Retreat w/ Pool Near Greenwood Lake

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (14 reviews)
"The property was well maintained, it felt very cozy and well located in the town. Host were amazing as they were always present to help me with any problem I had even though I never needed them."
United States
Sebastian A.
The price is ¥17,311
¥33,740 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.0 out of 10, Wonderful, (2 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is ¥24,189
¥36,632 total
includes taxes & fees
Jun 21 - Jun 22
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is ¥31,929
¥52,765 total
includes taxes & fees
Jun 22 - Jun 23
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is ¥26,608
¥50,863 total
includes taxes & fees
Jul 5 - Jul 6
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
8.8 out of 10, Excellent, (3 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
The price is ¥36,284
¥77,541 total
includes taxes & fees
Jun 23 - Jun 24
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Private Pool House - Pool · Jacuzzi · Fireplace

Private Pool House - Pool · Jacuzzi · Fireplace
Pine Bush
The price is ¥46,443
¥74,954 total
includes taxes & fees
Jun 25 - Jun 26
Private Pool House - Pool · Jacuzzi · Fireplace

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay! It was the perfect size for our small family. The property was extremely well maintained and there was a lot to do near by. We would definitely book here again!"
United States
Marc
The price is ¥26,447
¥83,388 total
includes taxes & fees
Jun 28 - Jun 29
Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is ¥34,510
¥66,378 total
includes taxes & fees
Jun 21 - Jun 22
Hike & Fish: Outdoor Retreat Near Trails

Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is ¥55,326
¥112,554 total
includes taxes & fees
Jun 25 - Jun 26
Bright Cornwall-on-hudson Vacation Rental!

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
3.0 star property
Vernon
Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
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

Find out more about Middletown

Middletown Cottages information

Number of reviews
4
Accommodation
130 Cottages
Lowest Price
¥66,378
Highest Price
¥112,554

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What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.