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

Search Middletown Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 AU$541
includes taxes & fees
3 Oct - 4 Oct
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 AU$423
includes taxes & fees
4 Oct - 5 Oct
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 AU$492
includes taxes & fees
13 Oct - 14 Oct
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
9.6 out of 10, Exceptional, (5 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is AU$316
includes taxes & fees
5 Oct - 6 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A house with a view of a bridge and mountains.

5. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AU$473
includes taxes & fees
20 Oct - 21 Oct
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

6. 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)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is AU$344
includes taxes & fees
6 Oct - 7 Oct
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.

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

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
9.0 out of 10, Wonderful, (4 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 AU$677
includes taxes & fees
5 Oct - 6 Oct
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 AU$555
includes taxes & fees
6 Oct - 7 Oct
Cozy Cottage w/ Hot Tub! — Family Friendly
A covered patio with wicker furniture, a fire pit, and a view of a grassy area.

9. 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 AU$1,372
includes taxes & fees
8 Oct - 9 Oct
Lakefront | Sport Courts | HotTub | GameRoom
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

10. 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 AU$1,005
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-on-hudson Vacation Rental!
An outdoor patio with a stone wall, a wooden fence, and a table with chairs.

11. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is AU$907
includes taxes & fees
4 Oct - 5 Oct
Updated Home w/ Patio Half Mile to West Point
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

10/10 Excellent
"Breakfast was the best I ever had for a free breakfast"
Lori 1-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Middletown - Goshen by IHG

Find out more about Middletown

Middletown Cottages information

Number of reviews
234
Accommodation
140 Cottages
Lowest Price
AU$316
Highest Price
AU$1,372

Frequently asked questions

What is there to do in Middletown near my cottage?
Middletown has enough activities and experiences to keep you on the go for weeks (or months!), starting with Paramount Theatre. Castle Fun Centre, Harness Racing Museum and Hall of Fame and Highland Lakes State Park are other renowned attractions. If you're staying a while longer, Orange County Fair Speedway and Thomas Bull Memorial Park will add the finishing touches to your itinerary.