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Featured Cottages in Middletown

Hike & Fish: Outdoor Retreat Near Trails
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Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is P10,417
P18,418 total
includes taxes & fees
Aug 24 - Aug 25
Hike & Fish: Outdoor Retreat Near Trails
6 Mi to Bethel Woods: Cabin w/ Pool Access
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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!
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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!
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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
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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!
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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!
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
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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!
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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!
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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!
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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!
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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
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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!
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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!
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Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property
Historic 1800s Cornwall-on-hudson Cottage!
Waterfront Wallkill Duplex Home w/ Fire Pits!
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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
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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
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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!
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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
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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

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Good "
Elena 1-night trip
Posted 1 day ago
Resorts World Catskills Casino

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.
How can I find cheap cottages in Middletown?
With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodations that'll make your wallet smile, narrow down your search by budget, amenities and star rating.
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.