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Holiday Homes in Montgomery

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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 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Montgomery and around

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Exterior

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

10.0 out of 10, Exceptional, (1)
"Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!"
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (10)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is €226
includes taxes & fees
17 Aug - 18 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Rustic Cabin in Fishkill!
Exterior

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is €367
includes taxes & fees
18 Aug - 19 Aug
Rustic Cabin in Fishkill!
Hickory on Willow Lake
Children’s area

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is €535
includes taxes & fees
15 Sept - 16 Sept
Hickory on Willow Lake
Chestnut on Willow Lake
Private kitchen

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is €507
includes taxes & fees
16 Sept - 17 Sept
Chestnut on Willow Lake
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (28)
"Jose has a wonderful home! Beautiful and quiet stay in a well-equipped spaced. My family had a lovely time. "
The price is €290
includes taxes & fees
31 Aug - 1 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
West Point Family Retreat, 5 min walk to Thayer!
Exterior

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is €715
includes taxes & fees
18 Aug - 19 Aug
West Point Family Retreat, 5 min walk to Thayer!
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is €319
includes taxes & fees
27 Aug - 28 Aug
Lovely 3BR Home with parking-Walk to WP Gate!
Fabulous 3bdrm Home w/parking!
Fridge, microwave, oven, stovetop

Fabulous 3bdrm Home w/parking!

8.0 out of 10, Very good, (2)
"Great place. Close to West Point activity. Clean and new."
The price is €269
includes taxes & fees
18 Aug - 19 Aug
Fabulous 3bdrm Home w/parking!
Cozy Escape -Strong Wi-Fi -Prime Location
Fridge, microwave, oven, stovetop

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
The price is €320
includes taxes & fees
9 Sept - 10 Sept
Cozy Escape -Strong Wi-Fi -Prime Location
King Bed | Private Parking | Strong WiFi
Smart TV

King Bed | Private Parking | Strong WiFi

The price is €299
includes taxes & fees
17 Aug - 18 Aug
King Bed | Private Parking | Strong WiFi
Large, Cozy, Bright Business Class Corporate Retreat
Interior

Large, Cozy, Bright Business Class Corporate Retreat

9.0 out of 10, Wonderful, (13)
"Very cozy stay with responsive host"
The price is €592
includes taxes & fees
17 Aug - 18 Aug
Large, Cozy, Bright Business Class Corporate Retreat
complete privacy vacation home [private pool]
Pool

complete privacy vacation home [private pool]

9.8 out of 10, Exceptional, (8)
"Wonderful property! The pool was so fun!"
complete privacy vacation home [private pool]
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (302)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is €527
includes taxes & fees
25 Aug - 26 Aug
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
The Meyer: spacious family home with hot tub minutes to downtown New Paltz
Fridge, microwave, oven, stovetop

The Meyer: spacious family home with hot tub minutes to downtown New Paltz

10.0 out of 10, Exceptional, (7)
"We loved our stay at this house. There were TONS of amenities, plenty of room and very clean. The backyard is lovely and we totally enjoyed the hot tub. Would definitely recommend!"
The price is €318
includes taxes & fees
19 Aug - 20 Aug
The Meyer: spacious family home with hot tub minutes to downtown New Paltz
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Private kitchen

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is €574
includes taxes & fees
1 Sept - 2 Sept
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Welcome to The Boathouse! Waterfront/Boats/Hot tub
Property grounds

Welcome to The Boathouse! Waterfront/Boats/Hot tub

10.0 out of 10, Exceptional, (3)
"Always love to stay in the New Paltz area. Good for the soul."
Welcome to The Boathouse! Waterfront/Boats/Hot tub
The Perfect Essential Getaway!
Interior

The Perfect Essential Getaway!

9.6 out of 10, Exceptional, (5)
"Owner was very responsive and accommodating on the app when I had questions. Place was great."
The Perfect Essential Getaway!
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Fridge, microwave, oven, stovetop

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (12)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is €520
includes taxes & fees
4 Sept - 5 Sept
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
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

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"Everything was great!"
Michelle 1-night trip
Posted 17 hours ago
Hampton Inn by Hilton New Paltz