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Holiday Homes in Montgomery

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Montgomery holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

1. Luxury 3BR with King Beds in Montgomery Village

Luxury 3BR with King Beds in Montgomery Village
Montgomery
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
The price is AU$698
includes taxes & fees
16 Nov - 17 Nov
Luxury 3BR with King Beds in Montgomery Village
A hallway with wooden flooring, white walls, a staircase with white railings, and a door at the end.

2. Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens

Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens
Montgomery
The price is AU$1,195
includes taxes & fees
16 Nov - 17 Nov
Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens
A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

3. New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!

New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
Montgomery
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home, attentive hosts, and the hot tub was great!"
United States
Kyle F.
The price is AU$2,047
includes taxes & fees
1 Nov - 2 Nov
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

4. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (18 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is AU$206
includes taxes & fees
28 Oct - 29 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

5. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (61 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
The price is AU$560
includes taxes & fees
2 Nov - 3 Nov
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A lakeside view with a picnic table and chairs, a grill, and a clear sky.

6. Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains

Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
wallkill
9.6 out of 10, Exceptional, (5 reviews)
"Everything was very nice, clean, easy access to things and great location!Loved the area! Host was wonderful!!I’d stay there again!!"
United States
Dauna A.
The price is AU$735
includes taxes & fees
2 Nov - 3 Nov
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

7. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (43 reviews)
"We really enjoyed a second stay at the De Vita House. The place is so clean and comfortable, and the location is great. Karin is a great host--she immediately dropped off a couple kitchen items we thought we needed--wasn't even an emergency or anything! Absolutely recommend."
United States
Natalie R.
The price is AU$622
includes taxes & fees
5 Nov - 6 Nov
The DeVita House Est. 1900
A forest campsite with a tent, a fire pit, and a bench.

8. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is AU$219
includes taxes & fees
25 Oct - 26 Oct
Glamping Tent & Campsite by Minnewaska State Park
A spacious living room with a high ceiling, large windows, a fireplace, and a cozy seating area.

9. Modern 5 Acre Farm Retreat with Game Room, Views, Privacy, and Proximity!

Modern 5 Acre Farm Retreat with Game Room, Views, Privacy, and Proximity!
Pine Bush
9.4 out of 10, Exceptional, (51 reviews)
"It filled our needs and we were happy with our visit to the area."
United States
Olivia M.
The price is AU$1,006
includes taxes & fees
15 Nov - 16 Nov
Modern 5 Acre Farm Retreat with Game Room, Views, Privacy, and Proximity!
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

10. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
10.0 out of 10, Exceptional, (12 reviews)
"Great space! Very nicely decorated. Host was very responsive and answered questions quickly. Also close to a great bakery and coffee shop!"
United States
Julie
The price is AU$419
includes taxes & fees
16 Nov - 17 Nov
Zen House at the Mountain Ridge
A bedroom with a large bed, a window with a view of trees, and an open door leading to a patio.

11. Private Forest Estate - Pool · Theater · Game Room . Sleep 18

Private Forest Estate - Pool · Theater · Game Room . Sleep 18
Pine Bush
10.0 out of 10, Exceptional, (2 reviews)
"Just returned from a 3 generation family celebration. This house was exactly as described. So beautiful, had all the amenities. More areas to relax, party, or just enjoy. The pool and pool house were just amazing. Kitchen and dining areas were great to work and enjoy. Basement had so many games to choose from. We already planning a return. Liliana was a terrific host, she responded to all our requests within minutes. Thank you so much."
United States
Greta U.
The price is AU$2,419
includes taxes & fees
30 Oct - 31 Oct
Private Forest Estate - Pool · Theater · Game Room . Sleep 18
A modern kitchen with a large island, built-in appliances, and a dining area with a view of trees.

12. CREATIVES DREAM GETAWAY

CREATIVES DREAM GETAWAY
Gardiner
9.6 out of 10, Exceptional, (10 reviews)
"We had a great stay at this lovely house in Gardiner. The main living floor is elevated (by about 5 steps) which provides nice clean views in the treetops. The backyard set up was lovely (bring bugspray) – with a designer pool and the most relaxing hot tub. Kitchen was well equipped and bedrooms were comfortable. Host was incredibly responsive. Would definitely recommend."
United States
Ashley R.
CREATIVES DREAM GETAWAY
A deck with Adirondack chairs, a fire pit, and a grill.

13. 3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point

3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
Cornwall
10.0 out of 10, Exceptional, (16 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is AU$610
includes taxes & fees
3 Nov - 4 Nov
3BR Home with Fireplace & Hudson Valley views near Woodbury Commons, West Point
A wooden deck with a metal fire pit, a bench with cushions, and a table with chairs.

14. The Under Ridge Home - 4 Bedroom w/Fireplace

The Under Ridge Home - 4 Bedroom w/Fireplace
Gardiner
9.2 out of 10, Wonderful, (20 reviews)
"The house was lovely! Very tastefully decorated with everything we needed. The deck out back was nice with gorgeous trees surrounding it. Our host was super fast to respond to any of our questions. Would stay here again!"
United States
Maureen C.
The Under Ridge Home - 4 Bedroom w/Fireplace
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

15. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (47 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is AU$304
includes taxes & fees
1 Nov - 2 Nov
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A fireplace with logs, a vase with flowers, and candles on a woven mat.

16. Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"It was great! "It's about a whale"."
United States
jwinegra W.
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

17. House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
9.8 out of 10, Exceptional, (14 reviews)
"We had a very comfortable stay. Nice quaint village. Area was quiet and easy to get to."
United States
Leann M.
The price is AU$612
includes taxes & fees
26 Oct - 27 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
A hot tub in a lush garden with a stone wall and outdoor furniture.

18. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (69 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is AU$752
includes taxes & fees
22 Nov - 23 Nov
Country House w/Hot Tub, Deck, Grill & Fire Pit
A window with a view of a green, leafy outdoor area, possibly a garden or park.

19. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (21 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is AU$180
includes taxes & fees
1 Nov - 2 Nov
Trails Head Tiny House
A staircase with red carpeted steps, wooden handrails, and string lights.

20. Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (17 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AU$771
includes taxes & fees
1 Nov - 2 Nov
Large,Cozy,Bright Apartment, Business Themed.
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"The arrival was easy and three lady was awesome! Great customer service"
Ana 2-night trip
Posted 5 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Montgomery

Montgomery Holiday Homes information

Number of reviews
390
Accommodation
402 Holiday Homes
Lowest Price
AU$180
Highest Price
AU$2,419