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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Browse Select Middletown Cottages

Hike & Fish: Outdoor Retreat Near Trails
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is ฿5,913
฿10,455 total
includes taxes & fees
20 Aug - 21 Aug
Hike & Fish: Outdoor Retreat Near Trails
6 Mi to Bethel Woods: Cabin w/ Pool Access
House (1 Bedroom) | Interior

6 Mi to Bethel Woods: Cabin w/ Pool Access

3.0 star property
6 Mi to Bethel Woods: Cabin w/ Pool Access
5 Mi to Marina & Raceways: Mongaup Valley Retreat!
House (2 Bedrooms) | Interior

5 Mi to Marina & Raceways: Mongaup Valley Retreat!

3.0 star property
5 Mi to Marina & Raceways: Mongaup Valley Retreat!
Luxe Family Home on Orange Lake w/ Private Dock!
House (3 Bedrooms) | Interior

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

3.0 star property
10.0 out of 10, Exceptional, (1)
"Excelent House 👏👌👌"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Kiamesha Lake Home w/ Deck: 4 Mi to Resorts World!
House (3 Bedrooms) | Interior

Kiamesha Lake Home w/ Deck: 4 Mi to Resorts World!

3.0 star property
Kiamesha Lake Home w/ Deck: 4 Mi to Resorts World!
Huguenot Retreat w/ Screened Porch & Lake Access!
Cottage (4 Bedrooms) | Front of property

Huguenot Retreat w/ Screened Porch & Lake Access!

3.0 star property
Huguenot Retreat w/ Screened Porch & Lake Access!
Charming Gardiner Home w/ Yard & Sunroom
House (4 Bedrooms) | Interior

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Gardiner Home w/ Yard & Sunroom
Family Home Close to Warwick, 5 Mi to Lake!
House (4 Bedrooms) | Interior

Family Home Close to Warwick, 5 Mi to Lake!

3.0 star property
Family Home Close to Warwick, 5 Mi to Lake!
Play, Swim & Unwind: Family Home in Glen Wild!
House (4 Bedrooms) | Interior

Play, Swim & Unwind: Family Home in Glen Wild!

3.0 star property
Play, Swim & Unwind: Family Home in Glen Wild!
Bright Cornwall-on-hudson Vacation Rental!
House (3 Bedrooms) | Interior

Bright Cornwall-on-hudson Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
Bright Cornwall-on-hudson Vacation Rental!
All-season Vernon Township Lake House Retreat!
Interior

All-season Vernon Township Lake House Retreat!

3.0 star property
All-season Vernon Township Lake House Retreat!
Charming Victorian Retreat w/ Hudson River Views
House (3 Bedrooms) | Interior

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views
Charming Highland Falls Home < 2 Mi to West Point!
House (4 Bedrooms) | Interior

Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property
Charming Highland Falls Home < 2 Mi to West Point!
Historic 1800s Cornwall-on-hudson Cottage!
Cottage (2 Bedrooms) | Interior

Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property
Historic 1800s Cornwall-on-hudson Cottage!
Waterfront Wallkill Duplex Home w/ Fire Pits!
House (3 Bedrooms) | Interior

Waterfront Wallkill Duplex Home w/ Fire Pits!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great for my kids and family for options to play outdoors and indoors games together. Loved the coffee bar and the details in the bathrooms with all the little things we could use down to the qtips and things. Really great for our family trip memories!!"
Waterfront Wallkill Duplex Home w/ Fire Pits!
Eclectic Ulster County Cabin w/ Private Hot Tub
House (5 Bedrooms) | Interior

Eclectic Ulster County Cabin w/ Private Hot Tub

3.0 star property
10.0 out of 10, Exceptional, (1)
"Was nice and secluded and felt very intimate"
Eclectic Ulster County Cabin w/ Private Hot Tub
Updated Home w/ Patio Half Mile to West Point
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

3.0 star property
Updated Home w/ Patio Half Mile to West Point
Port Jervis Home ~ 8 Acres w/ Mountain View!
House (3 Bedrooms) | Interior

Port Jervis Home ~ 8 Acres w/ Mountain View!

3.0 star property
Port Jervis Home ~ 8 Acres w/ Mountain View!
Warwick Vacation Rental w/ Private Yard & Fire Pit
House (4 Bedrooms) | Interior

Warwick Vacation Rental w/ Private Yard & Fire Pit

3.0 star property
10.0 out of 10, Exceptional, (1)
"I was relieved to find that the property looks just like and even better than the pictures online. "
Warwick Vacation Rental w/ Private Yard & Fire Pit
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Bed was comfortable and room was clean and good size Thank you!will come back"
Anna 1-night trip
Posted 1 day ago
Overlook Lodge at Bear Mountain

Frequently asked questions

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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.