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Our top choices for Montgomery holiday homes
1. Luxury 3BR with King Beds in Montgomery Village
Luxury 3BR with King Beds in Montgomery VillageMontgomery
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. "
Barbara M.
The price is NZ$822
includes taxes & fees
15 Nov - 16 Nov
2. Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens
Modern Home, 5BR, 4.5 bath, King Beds, 2 KitchensMontgomery
The price is NZ$1,454
includes taxes & fees
15 Nov - 16 Nov
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!"
Kyle F.
The price is NZ$1,942
includes taxes & fees
15 Nov - 16 Nov
4. A Cozy Private Suite in a Country Home near New Paltz
A Cozy Private Suite in a Country Home near New PaltzWallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
Carrie
The price is NZ$240
includes taxes & fees
16 Nov - 17 Nov
5. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltzwallkill
9.8 out of 10, Exceptional, (61 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
Debbie M.
The price is NZ$726
includes taxes & fees
14 Dec - 15 Dec
6. 3BR Hudson Valley home perfect for families!
3BR Hudson Valley home perfect for families!Wallkill
10.0 out of 10, Exceptional, (6 reviews)
"This property was lovely and peaceful! We enjoyed the stay in the area! Very clean and neat. Easy to use technology and check-in/out."
Cheryl N.
The price is NZ$936
includes taxes & fees
22 Nov - 23 Nov
7. Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountainswallkill
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!!"
Dauna A.
The price is NZ$966
includes taxes & fees
22 Nov - 23 Nov
8. The Columbus Hotel - The Courtyard Suite - 89-303
The Columbus Hotel - The Courtyard Suite - 89-303Middletown
The price is NZ$330
includes taxes & fees
14 Dec - 15 Dec
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."
Olivia M.
The price is NZ$917
includes taxes & fees
15 Nov - 16 Nov
10. The DeVita House Est. 1900
The DeVita House Est. 1900Gardiner
10.0 out of 10, Exceptional, (46 reviews)
"The house was in a perfect location! Host was very easy to communicate with!"
Matthew
The price is NZ$802
includes taxes & fees
15 Nov - 16 Nov
11. Zen House at the Mountain Ridge
Zen House at the Mountain RidgeGardiner
10.0 out of 10, Exceptional, (13 reviews)
"The house was perfect and really well decorated. The area it was in, proximity to everything. Couldn't have asked for a better spot."
Theresa
The price is NZ$386
includes taxes & fees
19 Nov - 20 Nov
12. 3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.Goshen
8.0 out of 10, Very good, (1 review)
"The check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
Kelly M.
The price is NZ$858
includes taxes & fees
3 Dec - 4 Dec
13. NEW! Cozy 3BR Home Near West Point & Hudson Valley - King Bed
NEW! Cozy 3BR Home Near West Point & Hudson Valley - King BedNew Windsor
The price is NZ$854
includes taxes & fees
15 Nov - 16 Nov
14. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Relaxed Mountain Living Near Minnewaska | Dream House in the GunksKerhonkson
10.0 out of 10, Exceptional, (48 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
Sueane
The price is NZ$334
includes taxes & fees
1 Dec - 2 Dec
15. Trails Head Tiny House
Trails Head Tiny HouseRock Hill
8.8 out of 10, Excellent, (23 reviews)
"Host was very friendly and helpful. "
Michael R.
The price is NZ$210
includes taxes & fees
16 Nov - 17 Nov
16. Private Forest Estate - Pool · Theater · Game Room . Sleep 18
Private Forest Estate - Pool · Theater · Game Room . Sleep 18Pine 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."
Greta U.
The price is NZ$2,677
includes taxes & fees
4 Dec - 5 Dec
17. Country House w/Hot Tub, Deck, Grill & Fire Pit
Country House w/Hot Tub, Deck, Grill & Fire PitGoshen
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. "
Mike T.
The price is NZ$930
includes taxes & fees
18 Nov - 19 Nov
18. 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 GunksKerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
Kyle T.
The price is NZ$346
includes taxes & fees
2 Dec - 3 Dec
19. Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of TownWarwick
8.8 out of 10, Excellent, (28 reviews)
"Great value and beautiful room and In ."
Paul E.
The price is NZ$280
includes taxes & fees
17 Nov - 18 Nov
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"
Adhith P.
The price is NZ$953
includes taxes & fees
23 Nov - 24 Nov
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.
Learn more about Montgomery
Stroll through charming streets lined with historic buildings, soaking in the small-town atmosphere of this Hudson Valley gem. Explore nearby wineries and parks, or catch a show at the City Winery for a perfect blend of culture and nature.
Top reviews in Montgomery
Harvest Inn
Harvest InnPine Bush
10/10 Excellent
Lovely hotel with wonderful staff. Very close to great dining eg Classic diner and Pine Bush Chinese . It’s positioned in a lovely area and has a very nice outdoor seating area where you can sit outside and enjoy the sun sets . I removed one star as the air conditioner in our room was very noisy with a musty smell but everything else was perfect .
jodie
