Lodging Image

Holiday Homes in Montgomery

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (4 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
Luxury 3BR with King Beds in Montgomery Village
A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

2. 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 €1,245
includes taxes & fees
26 Oct - 27 Oct
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.

3. 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, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is €123
includes taxes & fees
29 Sept - 30 Sept
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.

4. 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, (60 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
The price is €354
includes taxes & fees
29 Sept - 30 Sept
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A modern hotel room with a large bed, a desk, a chair, a TV, and a wardrobe.

5. The Columbus Hotel - The Courtyard Suite - 89-303

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is €177
includes taxes & fees
27 Sept - 28 Sept
The Columbus Hotel - The Courtyard Suite - 89-303
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

6. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (40 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is €396
includes taxes & fees
5 Oct - 6 Oct
The DeVita House Est. 1900
A forest campsite with a tent, a fire pit, and a bench.

7. 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 €137
includes taxes & fees
27 Sept - 28 Sept
Glamping Tent & Campsite by Minnewaska State Park
A modern kitchen with granite countertops, dark cabinetry, and a built-in island with bar stools.

8. 3BR Hudson Valley home perfect for families!

3BR Hudson Valley home perfect for families!
Wallkill
10.0 out of 10, Exceptional, (5 reviews)
"A friend and I needed to book a last minute stay. This house exceeded our expectations. It was clean and comfortable and had everything we needed. It was a great location as well!"
United States
Rachel S.
3BR Hudson Valley home perfect for families!
A lakeside view with a picnic table and chairs, a grill, and a clear sky.

9. 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.
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
A two-story house with a porch, a red door, and a small outdoor seating area with chairs and a table.

10. 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, (12 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 €355
includes taxes & fees
27 Sept - 28 Sept
House on the Babbling Brook- Quiet 2BR + King Bed!
A room with a bay window, a wooden table with a vase of flowers, and two upholstered chairs.

11. Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
8.6 out of 10, Excellent, (19 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is €140
includes taxes & fees
28 Sept - 29 Sept
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

12. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
9.8 out of 10, Exceptional, (9 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
Zen House at the Mountain Ridge
A deck with Adirondack chairs, a fire pit, and a grill.

13. 3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (15 reviews)
"Everything you could ask for!!"
United States
Elisabeth
The price is €369
includes taxes & fees
27 Sept - 28 Sept
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
A fireplace with logs, a vase with flowers, and candles on a woven mat.

14. 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.
The price is €201
includes taxes & fees
26 Oct - 27 Oct
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
A modern kitchen with a white island, stainless steel appliances, and wooden flooring.

15. Nurser * Private Garden * Minutes to Minnewaska

Nurser * Private Garden * Minutes to Minnewaska
Pine Bush
10.0 out of 10, Exceptional, (4 reviews)
"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."
United States
Amy L.
Nurser * Private Garden * Minutes to Minnewaska
A window with a view of a green, leafy outdoor area, possibly a garden or park.

16. 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 €122
includes taxes & fees
28 Sept - 29 Sept
Trails Head Tiny House
A bedroom with a bed, a TV mounted on the wall, a window with a view of greenery, and a small seating area with a table and chairs.

17. The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very good, (46 reviews)
"The pictures are misleading"
United States
Jia
The price is €245
includes taxes & fees
27 Sept - 28 Sept
The Studio at the Inn at High Falls
A kitchen with wooden shelves, a window with a view of trees, and a vase with flowers on the windowsill.

18. 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, (45 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is €243
includes taxes & fees
4 Oct - 5 Oct
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

19. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (10 reviews)
"Came in to town for a bachelor party weekend and had a great time. Rooms were clean and nice, scenery was beautiful, and the host was very responsive. Beds were comfy but could use some more pillows. Kitchen/dining room was convenient but could definitely use a bigger fridge for people who want to bring stuff for meals. Overall great experience!"
United States
Nate R.
The price is €305
includes taxes & fees
27 Sept - 28 Sept
Hike & Fish: Outdoor Retreat Near Trails
A hot tub in a lush garden with a stone wall and outdoor furniture.

20. 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, (67 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 €526
includes taxes & fees
27 Sept - 28 Sept
Country House w/Hot Tub, Deck, Grill & Fire Pit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montgomery Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"Was definitely worth the price. Much more than I expected for this area. Friendly staff, clean rooms, convenient location and very comfortable."
ELANA 1-night trip
Posted less than an hour ago
Holiday Inn Express Hotel & Suites Chester by IHG

Find out more about Montgomery

Montgomery Holiday Homes information

Number of reviews
416
Accommodation
402 Holiday Homes
Lowest Price
€122
Highest Price
€1,245