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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Middletown cottages

Exterior

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 HK$1,271
HK$3,274 total
includes taxes & fees
19 Jul - 20 Jul
Hello Small Stone
Property grounds

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 HK$1,553
HK$2,594 total
includes taxes & fees
6 Jul - 7 Jul
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Interior

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 HK$1,663
HK$4,052 total
includes taxes & fees
19 Jul - 20 Jul
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Property grounds

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 HK$1,176
HK$1,807 total
includes taxes & fees
5 Jul - 6 Jul
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Smart TV

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 HK$1,165
HK$2,295 total
includes taxes & fees
5 Jul - 6 Jul
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

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 HK$1,095
HK$1,859 total
includes taxes & fees
3 Aug - 4 Aug
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Outdoor dining

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 HK$1,765
HK$3,795 total
includes taxes & fees
15 Jul - 16 Jul
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Property grounds

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (8 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 HK$1,294
HK$4,100 total
includes taxes & fees
19 Jul - 20 Jul
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Interior

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is HK$1,898
HK$3,232 total
includes taxes & fees
5 Jul - 6 Jul
Hike & Fish: Outdoor Retreat Near Trails
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

Tru by Hilton Middletown

Tru by Hilton Middletown

8/10 Good
"We like the room and the breakfast and the coffee all day. The price was high."
Christopher 2-night trip
Posted 5 hours ago
Tru by Hilton Middletown

Find out more about Middletown

Middletown Cottages information

Number of reviews
187
Accommodation
135 Cottages
Lowest Price
HK$1,807
Highest Price
HK$4,100

Frequently asked questions

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How can I find cheap cottages in Middletown?
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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.

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