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Aug 15 - Aug 17
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Browse Select Montgomery Cottages

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

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…."
The price is CA $278
CA $449 total
includes taxes & fees
Aug 6 - Aug 7
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Charming Cottage in the Heart of the Shawangunks
Exterior

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."
The price is CA $379
CA $831 total
includes taxes & fees
Sep 3 - Sep 4
Charming Cottage in the Heart of the Shawangunks
Hello Small Stone
Exterior

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."
The price is CA $223
CA $575 total
includes taxes & fees
Aug 6 - Aug 7
Hello Small Stone
Hike & Fish: Outdoor Retreat Near Trails
House (1 Bedroom) | Interior

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
The price is CA $252
CA $446 total
includes taxes & fees
Aug 6 - Aug 7
Hike & Fish: Outdoor Retreat Near Trails
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
Property grounds

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
Exterior

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
Leggett Cottage, High Falls, NY.
Exterior

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (76)
"We really enjoyed our stay! The space was very nice & beautiful during the fall!"
Leggett Cottage, High Falls, NY.
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Outdoor dining

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

9.6 out of 10, Exceptional, (13)
"The house was exactly as advertised. It was clean, well maintained and comfortable! The location was beautiful and private yet close to nearby stores and activities."
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

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

The price is CA $193
CA $294 total
includes taxes & fees
Aug 13 - Aug 14
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
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
Cozy Haven: A Romantic Retreat in our Tiny House!
Exterior

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is CA $207
CA $407 total
includes taxes & fees
Aug 13 - Aug 14
Cozy Haven: A Romantic Retreat in our Tiny House!
Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Exterior

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC

Charming 2-bedroom cottage in delightful Greenwood Lake with WiFi, AC
Charming Lakefront Cottage On Masten lake
Property grounds

Charming Lakefront Cottage On Masten lake

9.8 out of 10, Exceptional, (35)
"We really enjoyed this cozy little college next to the lake. It was a perfect place to stay when going to multiple nights of concerts at Bethel Woods. We would love to return some time. The owner is kind and communicative and the entire process was very stress free. Great little place for a couple."
Charming Lakefront Cottage On Masten lake
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 (3 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
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Exterior

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

10.0 out of 10, Exceptional, (13)
"This property was outstanding and impeccable in every way. Much thought was given to everything a traveler could use or need. I could easily stay here for a month or more because it felt like a comfortable home. Many thanks to the owner of the property!"
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
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!
Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (60)
"It’s adorable exactly What’s on the photos and equipped with everything you need for your stay definitely will be visiting it again. "
Mountain View escape
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 Montgomery 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 12 hours ago
Sleep Inn & Suites Middletown - Goshen