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Compare 390 Vacation Homes in Montgomery with updated reviews, rates, and availability.

Beautiful Private Stone Home in the Hudson Valley
Exterior
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
Red Barn Retreat - Shawangunk Mountains Getaway
Property grounds
Red Barn Retreat - Shawangunk Mountains Getaway
10.0 out of 10, Exceptional, (31)
"This was an absolutely amazing stay. My husband and I hand an amazing time with our two dogs celebrating our anniversary. We plan on returning again because we hand such a lovely time. We were greeted by our host who was so kind and helpful. All the recommendations were amazing and really helped us plan out our short time there. I wish we were able to stay longer but again we will be returning in the future!"
Red Barn Retreat - Shawangunk Mountains Getaway
complete privacy vacation home [private pool]
Pool
complete privacy vacation home [private pool]
9.6 out of 10, Exceptional, (4)
"Our family stayed here while visiting a nephew at West Point, around 35 min away. The house was very clean and check-in was flawless. The beds and pillows were comfortable. We spent a lot of time in the game room playing ping pong, air hockey, and pool. We did not swim in the pool but it looked amazing. A perfect place for us and we will definitely return if in the area again."
The price is AED 2,626
AED 4,068 total
includes taxes & fees
17 Nov - 18 Nov
complete privacy vacation home [private pool]
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Exterior
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is AED 1,485
AED 3,076 total
includes taxes & fees
18 Nov - 19 Nov
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Eating area leading to one pristeen acre looking out to waterfront
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is AED 643
AED 1,316 total
includes taxes & fees
17 Nov - 18 Nov
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
Schawangunk House
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
8.8 out of 10, Excellent, (16)
"Close to the trails. Loved the park with the trails. "
Cute home in Kerhonkson, NY. This home is minutes to many popular destinations
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Garrison Vacation Rental | 2BR | 2.5BA | 1,700 Sq Ft | 1 Step to Enter
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (22)
"House was beautifully furnished with lovely touches of art work and lovely succulent plants. The hot tub was a great touch, and we enjoyed it every morning. The children loved exploring the property. Thank you!"
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Nature Getaway: Charming Villa Near Trails and Parks
Interior
Nature Getaway: Charming Villa Near Trails and Parks
7.2 out of 10, Good, (9)
"Really cool house. We has some issues with our stay. It took a bit to get in touch with the manager to resolve the issues. The next day the brought most if the items needed that the h"
Nature Getaway: Charming Villa Near Trails and Parks
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
The open dining and living room area has plenty of comfortable seating.
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
10.0 out of 10, Exceptional, (2)
" This space was the perfect place to come back to after a day filled with fun fall activities. The property had everything we needed to cook a nice dinner. And there were ample entertainment provided options for the evening. The property was clean and spacious. It is a great place to stay, I would highly recommend it."
The price is AED 569
AED 938 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Pine Bush Vacation Rental | 1BR | 1.5BA | Stairs Required for Access | 750 Sq Ft
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Trails Head Tiny House
Updated picture of the exterior with the extended deck.
Trails Head Tiny House
9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AED 290
AED 455 total
includes taxes & fees
1 Dec - 2 Dec
Trails Head Tiny House
The Studio at the Inn at High Falls
Exterior
The Studio at the Inn at High Falls
7.8 out of 10, Good, (22)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The Studio at the Inn at High Falls
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
Master bedroom
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
9.0 out of 10, Wonderful, (4)
"The home was in a perfect spot with lake views and is nicely close to town. We picked the home for its closeness to the rein fair and I’m so glad we did, It was wonderfully quiet and relaxing after a long day of hanging out at the rein fair !"
Lakeview with Mountain View, Nature seeker friendly. Greenwood Lake
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Welcome to the Louie II. A serene setting for your next Hudson Valley getaway.
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
9.2 out of 10, Wonderful, (22)
"This property was clean and exactly as described. We were in the area for a family gathering and it allowed us a quiet place to regroup with our dog at night. Highly recommend and are hoping to visit again. "
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Exterior
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
9.6 out of 10, Exceptional, (24)
"Nice place to stay for anyone who wants to explore nyc surroundings parks and trails and nature!"
The price is AED 676
AED 1,213 total
includes taxes & fees
23 Nov - 24 Nov
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (117)
"The home is nestled in the woods and surrounded by amazing boulders . The mid century home is comfortable and stunning . We stayed at the house for a quiet weekend visiting friends in the area. The home is well equipped and a joy to stay and relax in . The area is a hikers dream and there are many amazing places to explore . The working fireplace adds a magical atmosphere. We hope to visit this property again . "
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Perfect for families and large groups
Come on in -- the water's fine! Who else is ready to take a dip and soak up some sun?
Perfect for families and large groups
9.4 out of 10, Exceptional, (10)
"Nice house with plenty of room and very clean."
Perfect for families and large groups
5 Acre Modern Mountain Farm
Exterior
5 Acre Modern Mountain Farm
9.4 out of 10, Exceptional, (28)
"We enjoyed our stay. The property is beautiful. Some extra bath towels would be nice. We would definitely stay again!"
The price is AED 1,043
AED 1,949 total
includes taxes & fees
2 Dec - 3 Dec
5 Acre Modern Mountain Farm
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
Minnewaska Lake
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
9.8 out of 10, Exceptional, (90)
"Very close to hiking and biking trails! Beds were comfortable "
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
Sweet and spacious mountain view home w/fireplace!
Living area
Sweet and spacious mountain view home w/fireplace!
9.8 out of 10, Exceptional, (18)
"Loved the layout and the amount of natural light"
Sweet and spacious mountain view home w/fireplace!
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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Other property types in Montgomery

Quaint village, walk to restaurants and shops.
Exterior detail
Quaint village, walk to restaurants and shops.
9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.
The Scenic Mansion With Breathtaking View
Property grounds
The Scenic Mansion With Breathtaking View
9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View
Trails Head Tiny House
Updated picture of the exterior with the extended deck.
Trails Head Tiny House
9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is AED 290
AED 455 total
includes taxes & fees
1 Dec - 2 Dec
Trails Head Tiny House
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.