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Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Montgomery holiday rentals

A wooden cabin with a covered deck, outdoor seating, and a fire pit.

1. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
9.8 out of 10, Exceptional, (6 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$932
HK$1,871 total
includes taxes & fees
3 Nov - 4 Nov
Historic Cabin with Pool & Fire Pit
A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

2. Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (20 reviews)
"Great hosts and great location!"
United States
Shelby A.
The price is HK$1,234
HK$2,406 total
includes taxes & fees
18 Oct - 19 Oct
Modern Hudson Valley Apt 202 - King/Queen/Twin
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

3. 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 HK$2,247
HK$3,936 total
includes taxes & fees
20 Oct - 21 Oct
Luxury 3BR with King Beds in Montgomery Village
A person ascending a stone staircase with a wooden railing, leading to a cabin with a dark exterior and a wooden deck.

4. Lux Cabin on Farm, River, Animals, Projector

Lux Cabin on Farm, River, Animals, Projector
Montgomery
The price is HK$2,607
HK$4,834 total
includes taxes & fees
28 Oct - 29 Oct
Lux Cabin on Farm, River, Animals, Projector
A dining area with a wooden table and chairs, a painting on the wall, and a kitchen with white cabinets.

5. Montgomery Village Center King Bed Ground Floor

Montgomery Village Center King Bed Ground Floor
Montgomery
The price is HK$2,253
HK$3,360 total
includes taxes & fees
22 Oct - 23 Oct
Montgomery Village Center King Bed Ground Floor
A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

6. 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 HK$6,910
HK$11,890 total
includes taxes & fees
22 Oct - 23 Oct
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
A kitchen with white cabinets, a black countertop, a stainless steel oven, and a microwave.

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

Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens
Montgomery
The price is HK$4,449
HK$6,845 total
includes taxes & fees
16 Nov - 17 Nov
Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens
A spacious living room with a sofa, armchairs, and a coffee table. A kitchen with modern appliances is visible in the background.

8. Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Montgomery
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful stay. Responded quickly to any issues even if it was a tiny one. Would absolutely stay here again. "
United States
Richard D.
The price is HK$1,635
HK$2,882 total
includes taxes & fees
19 Oct - 20 Oct
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

9. Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (101 reviews)
"Simple, clean, nice location, close to the river is a plus.Views were very nice, rear deck was a nice place to enjoy them."
United States
Dave and Sarah H.
The price is HK$1,044
HK$2,065 total
includes taxes & fees
2 Nov - 3 Nov
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

10. Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (31 reviews)
"Wonderful property will definitely book again."
United States
Jane G.
The price is HK$735
HK$1,526 total
includes taxes & fees
3 Nov - 4 Nov
Dream getaway apartment in the foot of Gunks Ridge
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

11. 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 HK$473
HK$1,013 total
includes taxes & fees
20 Oct - 21 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A living room with a fireplace, a painting, shelves with decorative items, and a television.

12. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is HK$1,130
HK$2,414 total
includes taxes & fees
22 Oct - 23 Oct
Grant - A Tranquil One Bedroom Steps from River
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

13. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (17 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is HK$1,295
HK$2,451 total
includes taxes & fees
12 Nov - 13 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
An outdoor seating area with red chairs and a fire pit, surrounded by rocks and trees, with string lights overhead.

14. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (24 reviews)
"Just what we were looking for"
United States
Natalya
The price is HK$1,158
HK$1,991 total
includes taxes & fees
20 Oct - 21 Oct
TRANQUIL MOUNTAIN SOLITUDE
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

15. 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 HK$1,573
HK$3,265 total
includes taxes & fees
1 Nov - 2 Nov
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

16. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (42 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is HK$1,177
HK$3,471 total
includes taxes & fees
18 Oct - 19 Oct
The DeVita House Est. 1900
A lakeside view with a picnic table and chairs, a grill, and a clear sky.

17. 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 HK$1,868
HK$4,289 total
includes taxes & fees
15 Nov - 16 Nov
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

18. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is HK$902
HK$1,492 total
includes taxes & fees
20 Oct - 21 Oct
Cabin in the heart of the Hudson Valley, Cabin 4
A forested area with a table and chairs on a wooden platform.

19. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.6 out of 10, Exceptional, (5 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is HK$1,099
HK$1,694 total
includes taxes & fees
19 Oct - 20 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

20. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is HK$981
HK$1,807 total
includes taxes & fees
21 Oct - 22 Oct
Cabin in the Heart of the Hudson Valley, Cabin 1
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
"Thanks!"
Michael 1-night trip
Posted less than an hour ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Montgomery

Search for holiday rentals in Montgomery on Expedia! You can easily find your home rentals, villas, holiday apartments in Montgomery using one of the methods below:

  • View our selection of featured holiday rentals in Montgomery
  • Use the map to find apartments and other holiday homes in the Montgomery neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montgomery while they last

Look no further and take a look at our great range of rental properties in Montgomery!

Frequently asked questions

Are there holiday rentals in Montgomery?

Yes, there are holiday rentals in Montgomery close to Orange County Arboretum, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Montgomery has a good selection of restaurants. Make sure you have time to check out the gardens and shopping during your trip.

What are some of the best holiday rentals that Montgomery has to offer?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Montgomery is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Montgomery?

Choose from 14 Expedia holiday rentals in Montgomery for a memorable holiday.

What can I see and do in Montgomery?

Thomas Bull Memorial Park and Orange County Arboretum are a couple of lovely local spots to get outside and enjoy nature. While here, Highland Lakes State Park and City Winery Hudson Valley are other places worth a visit.

What’s a holiday rental in Montgomery like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montgomery. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for small groups.