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Montgomery Holiday Rentals

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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 rentals

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 HK$2,246
HK$3,933 total
includes taxes & fees
16 Nov - 17 Nov
Luxury 3BR with King Beds in Montgomery Village
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
10.0 out of 10, Exceptional, (21 reviews)
"Great hosts and great location!"
United States
Shelby A.
The price is HK$1,234
HK$2,423 total
includes taxes & fees
27 Oct - 28 Oct
Modern Hudson Valley Apt 202 - King/Queen/Twin
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

3. 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$923
HK$1,832 total
includes taxes & fees
2 Nov - 3 Nov
Historic Cabin with Pool & Fire Pit
A modern living room with a sofa, a coffee table, and a dining area with chairs.

4. Montgomery Village Center King Bed Ground Floor

Montgomery Village Center King Bed Ground Floor
Montgomery
The price is HK$2,036
HK$3,142 total
includes taxes & fees
16 Nov - 17 Nov
Montgomery Village Center King Bed Ground Floor
A person ascending a stone staircase with a wooden railing, leading to a cabin with a dark exterior and a wooden deck.

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

Lux Cabin on Farm, River, Animals, Projector
Montgomery
Lux Cabin on Farm, River, Animals, Projector
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

6. 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$4,284
HK$6,660 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.

7. 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$1,397
HK$2,637 total
includes taxes & fees
27 Oct - 28 Oct
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
A modern kitchen with white cabinetry, a central island with stools, a built-in oven, and a stainless steel refrigerator.

8. 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$6,873
HK$11,835 total
includes taxes & fees
2 Nov - 3 Nov
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
Three wall-mounted shelves with decorative items, including a framed picture of a plant.

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, (102 reviews)
"Kelly and Joe’s property was beautiful, the check in and check out process was smooth and easy, and the location was perfect for our planned activities. The property made our special weekend even more perfect as a newly engaged couple!"
United States
Jessica
The price is HK$933
HK$1,924 total
includes taxes & fees
2 Nov - 3 Nov
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

10. 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 HK$1,387
HK$3,029 total
includes taxes & fees
1 Nov - 2 Nov
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A two-story house with a porch, a table, and chairs outside.

11. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is HK$1,666
HK$2,051 total
includes taxes & fees
8 Nov - 9 Nov
Historic Horse Barn Apartment in Goshen
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

12. 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, (32 reviews)
"Loved our stay! The house is cozy and well cared for. Plenty of room and everything we might have needed. Thanks so much for the nice message, it really shows that you care about your guests :)"
United States
Sara
The price is HK$679
HK$1,460 total
includes taxes & fees
3 Nov - 4 Nov
Dream getaway apartment in the foot of Gunks Ridge
A lakeside view with a picnic table and chairs, a grill, and a clear sky.

13. 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$1,712
HK$4,096 total
includes taxes & fees
1 Nov - 2 Nov
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

14. 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$1,165
HK$2,294 total
includes taxes & fees
1 Nov - 2 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

15. 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$565
HK$1,116 total
includes taxes & fees
28 Oct - 29 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.

16. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (52 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$1,059
HK$2,253 total
includes taxes & fees
9 Nov - 10 Nov
Grant - A Tranquil One Bedroom Steps from River
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

17. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (44 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 HK$1,176
HK$3,496 total
includes taxes & fees
27 Oct - 28 Oct
The DeVita House Est. 1900
A cozy living room with a sofa, a dining table, and a bed.

18. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Lovely cottage in a beautiful setting with everything you need to rest, relax, and enjoy this lovely part of New York state. Highly recommend!"
United States
Frances N.
The price is HK$1,451
HK$2,770 total
includes taxes & fees
27 Oct - 28 Oct
Cozy country efficiency in the Hudson Valley
An outdoor seating area with red chairs and a fire pit, surrounded by rocks and trees, with string lights overhead.

19. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (25 reviews)
"Just what we were looking for"
United States
Natalya
The price is HK$1,023
HK$1,814 total
includes taxes & fees
27 Oct - 28 Oct
TRANQUIL MOUNTAIN SOLITUDE
A forested area with a table and chairs on a wooden platform.

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

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.8 out of 10, Exceptional, (6 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is HK$1,098
HK$1,693 total
includes taxes & fees
27 Oct - 28 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"The room was clean but hall was less impressive. There was an odor. Staff was cordial but not knowledgeable. Advertisement says, continental breakfast not even hot tea was available."
Philip 1-night trip
Posted 1 hour ago
Ramada by Wyndham Newburgh/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.