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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 £276
includes taxes & fees
1 Nov - 2 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 £221
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 £257
includes taxes & fees
1 Nov - 2 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 £177
includes taxes & fees
1 Nov - 2 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 £158
includes taxes & fees
12 Nov - 13 Nov
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
An outdoor dining area with tables and chairs, surrounded by greenery and a view of the landscape.

6. 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 £336
includes taxes & fees
4 Nov - 5 Nov
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Exterior

7. 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 £301
includes taxes & fees
9 Nov - 10 Nov
Cozy Cottage w/ Hot Tub! — Family Friendly
A house with a view of a bridge and mountains.

8. 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, (149 reviews)
"We had a great stay!!"
United States
Jasmine
The price is £238
includes taxes & fees
2 Nov - 3 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A wooden deck with a 'COME IN' mat, white siding, and a view of dense green trees.

9. 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 £386
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

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"I love any property that allows animals. Free breakfast good Staff was very kind."
Sharon 1-night trip
Posted 4 hours ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Find out more about Middletown

Middletown Cottages information

Number of reviews
205
Accommodation
140 Cottages
Lowest Price
£158
Highest Price
£522

Frequently asked questions

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We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
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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.