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Search Middletown Cottages

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Cottages in Middletown

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
$288 nightly
The price is $326
Aug 6 - Aug 7
Total includes taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Cottage with Woodstock Scavenger Hunt
Surrounding a serene garden pond, lush greenery and diverse plant life create a peaceful atmosphere.

Cozy Cottage with Woodstock Scavenger Hunt

10.0 out of 10, Exceptional, (2)
"this spot was exactly what we needed for an overnight in the area. clean, easy to find, excellent communication and exactly as picturedsaving this for future needs for sure "
$247 nightly
The price is $278
Aug 7 - Aug 8
Total includes taxes and fees
Cozy Cottage with Woodstock Scavenger Hunt
Lazy River Cottage on the Delaware River
Enjoy a scenic view of the wooded area and body of water from the large window in this room.

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (154)
"Gorgeous location to unplug and connect with nature. Serene setting. Clean and charming. Host was lovely and responsive. Highly recommend. "
Lazy River Cottage on the Delaware River
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Enjoy riverside camping with a portable grill, firewood, and scenic views.

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

9.6 out of 10, Exceptional, (35)
"It is perfectly located by the river. Breathe taking views"
Tiny House on Spectacular Riverfront Property - Private Access to Delaware River
Charming 2-bedroom cottage in delightful Eldred with WiFi
Enjoy a refreshing swim in the circular pool surrounded by a deck and lounge chairs.

Charming 2-bedroom cottage in delightful Eldred with WiFi

10.0 out of 10, Exceptional, (1)
"This was a lovely little cottage on a shared property in a remote wooded area. The amenities (pool, fireplace, and trampoline) were great hits with my kids and the setting in the woods was stunning. The hosts were exceedingly gracious and kind. That said just note that the property is shared so you are utilizing the grounds of the host. "
Charming 2-bedroom cottage in delightful Eldred with WiFi
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Relax by the serene pool surrounded by lush greenery and a single chair for a peaceful retreat.

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

10.0 out of 10, Exceptional, (32)
"The cabin is in a great location for hiking and outdoor activities. We enjoyed the dog park and hiking trails close by. "
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Charming Cottage in the Heart of the Shawangunks
Enjoy cooking in this well-lit kitchen with a double sink, toaster oven, and a window overlooking the surrounding trees.

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
$534 nightly
The price is $598
Aug 24 - Aug 25
Total includes taxes and fees
Charming Cottage in the Heart of the Shawangunks
Magical, all season, multilevel treehouse on beautiful 120 acre property.
Escape to a secluded cabin surrounded by forest, with a multi-level deck and staircase leading to the upper floor.

Magical, all season, multilevel treehouse on beautiful 120 acre property.

10.0 out of 10, Exceptional, (3)
"Our two young children absolutely loved our stay at the treehouse! Such a unique and fun way to spend a few days in the woods!"
Magical, all season, multilevel treehouse on beautiful 120 acre property.
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Relax in a secluded hot tub surrounded by lush greenery and tall trees.

SwimSpa | Lake | Fish | Kayak | Hike | Firepit

9.6 out of 10, Exceptional, (4)
"Enjoyed our stay very much! Would highly recommend for someone seeking a nice quite get-away. Very nice Swim-spa for relaxation, many board games. We look forward to returning!"
$899 nightly
The price is $961
Aug 20 - Aug 21
Total includes taxes and fees
SwimSpa | Lake | Fish | Kayak | Hike | Firepit
Hello Small Stone
Escape to a cozy cabin surrounded by a forested landscape, featuring a porch, deck, and garden area.

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house was great. It was nice to sit and relax by the small pond in the back."
$369 nightly
The price is $417
Aug 6 - Aug 7
Total includes taxes and fees
Hello Small Stone
Hike & Fish: Outdoor Retreat Near Trails
Situated in a wooded area, this cabin offers a natural and secluded environment with a large garage door and a window overlooking the surrounding forest.

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
$291 nightly
The price is $324
Aug 10 - Aug 11
Total includes taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Escape to a serene lakeside retreat surrounded by autumn hues and tranquil waters.

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (102)
"For the dogs: our dogs enjoyed the big fenced-in backyard. There's also a HUGE fenced-in dog run a few minutes drive away. For the humans: My wife and I enjoyed the gaming options (Xbox, Playstation, and an arcade machine). There's a nice little town a few minutes drive away, with a supermarket, CVS, and decent coffee and food options."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
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!
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and granite countertops.

Hudson Valley Retreat w/ Pool Near Greenwood Lake

10.0 out of 10, Exceptional, (6)
"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!"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Bird Songs, Come Listen Awhile – Perfect for Remote Work & Weekend Getaways
Cozy house with a gabled roof and front porch, surrounded by a serene natural landscape.

Bird Songs, Come Listen Awhile – Perfect for Remote Work & Weekend Getaways

10.0 out of 10, Exceptional, (5)
"Very cool chill place to stay. Totally enjoyed my stay very relaxing."
Bird Songs, Come Listen Awhile – Perfect for Remote Work & Weekend Getaways
Designer renovated 2-Bedroom 1920s cottage in Sullivan County Catskills
Enjoy cooking in this well-equipped kitchen with a central island and appliances.

Designer renovated 2-Bedroom 1920s cottage in Sullivan County Catskills

10.0 out of 10, Exceptional, (2)
"This property is nicely designed and furnished. I recommend staying here if you’re looking for a quiet romantic getaway with a loved one in rural upstate NY. "
Designer renovated 2-Bedroom 1920s cottage in Sullivan County Catskills
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Outdoor dining

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

$192 nightly
The price is $216
Aug 10 - Aug 11
Total includes taxes and fees
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
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
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Relax in a secluded hot tub surrounded by lush forest.

2 Lake Cabins | Pool+HotTub | Game Room | 23acs

10.0 out of 10, Exceptional, (2)
"Gorgeous property for a family reunion. Host was very accommodating and responsive. Lots of fun amenities and room for everyone to spread out. Great open space on the lake but still felt private and quiet. Wifi throughout entire property. Absolutely recommend and would definitely book again."
$2,581 nightly
The price is $2,789
Aug 20 - Aug 21
Total includes taxes and fees
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
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!
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"We had a great stay here. The manager was the best (Corlina? Corvina?) Everything was clean and the room was super comfortable. And the breakfast was off the charts! Waffles, eggs, delicious pastries, French toast…. Best breakfast I’ve had at a hotel that was included with the room! The only negative was the pool area was overcrowded, loud and full of kids who couldn’t have been potty trained but weren’t in swim diapers…"
Oveta 1-night trip
Posted 19 hours ago
Sleep Inn & Suites Middletown - Goshen