A lake surrounded by autumn-colored trees reflecting on the water.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Middletown cottages

A rustic cabin with a stone exterior, wooden deck, and a small porch.

1. Hello Small Stone

Hello Small Stone
Middletown
9.8 out of 10, Exceptional, (7 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 AED 661
AED 1,546 total
includes taxes & fees
5 Nov - 6 Nov
Hello Small Stone
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is AED 545
AED 1,027 total
includes taxes & fees
12 Nov - 13 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A wooden deck with a barbecue grill and a trash can.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AED 779
AED 1,262 total
includes taxes & fees
5 Nov - 6 Nov
Hike & Fish: Outdoor Retreat Near Trails
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

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

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is AED 551
AED 803 total
includes taxes & fees
5 Nov - 6 Nov
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

5. 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, (18 reviews)
"Just what we needed .... place was spotless.....quiet.... peaceful."
United States
Victor M M.
The price is AED 420
AED 724 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

6. Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
Monroe
10.0 out of 10, Exceptional, (9 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 AED 606
AED 1,913 total
includes taxes & fees
8 Nov - 9 Nov
Hudson Valley Retreat w/ Pool Near Greenwood Lake
An outdoor dining area with tables and chairs, surrounded by greenery and a view of the landscape.

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

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.2 out of 10, Wonderful, (5 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 AED 864
AED 1,732 total
includes taxes & fees
9 Nov - 10 Nov
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Exterior

8. Cozy Cottage w/ Hot Tub! — Family Friendly

Cozy Cottage w/ Hot Tub! — Family Friendly
Mongaup Valley
10.0 out of 10, Exceptional, (10 reviews)
"we had gr8 time with our family even though it rained enjoyed brook fire pit hot tub tramperlin a great place to go with family very freindly host good communication than you alex !!!!"
United States
yisroel k.
The price is AED 591
AED 1,445 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Cottage w/ Hot Tub! — Family Friendly
A house with a view of a bridge and mountains.

9. 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, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AED 727
AED 1,158 total
includes taxes & fees
9 Nov - 10 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A covered patio with wicker furniture, a fire pit, and a view of a grassy area.

10. Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"We had a wonderful time and definitely would recommend!"
United States
Phillip C.
The price is AED 534
AED 2,984 total
includes taxes & fees
10 Nov - 11 Nov
Lakefront | Sport Courts | HotTub | GameRoom
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

11. 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, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is AED 779
AED 1,897 total
includes taxes & fees
8 Nov - 9 Nov
Hudson Valley Retreat w/ Pool Near Greenwood Lake
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

10/10 Excellent
"Great stay, great play area for the family in the lobby"
Jarrod 1-night trip
Posted 12 hours ago
Tru by Hilton Middletown

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