Holiday Rentals in Montgomery

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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 €211
includes taxes & fees
16 Nov - 17 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
10.0 out of 10, Exceptional, (21 reviews)
"Great hosts and great location!"
United States
Shelby A.
The price is €265
includes taxes & fees
10 Nov - 11 Nov
Modern Hudson Valley Apt 202 - King/Queen/Twin
A modern living room with a sofa, a coffee table, and a dining area with chairs.

3. Montgomery Village Center King Bed Ground Floor

Montgomery Village Center King Bed Ground Floor
Montgomery
The price is €280
includes taxes & fees
9 Nov - 10 Nov
Montgomery Village Center King Bed Ground Floor
A covered outdoor area with a paved walkway, a trash bin, and a vehicle parked in the background.

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

Modern Home, 5BR, 4.5 bath, King Beds, 2 Kitchens
Montgomery
The price is €791
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.

5. 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 €1,052
includes taxes & fees
12 Nov - 13 Nov
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
A spacious living room with a sofa, armchairs, and a coffee table. A kitchen with modern appliances is visible in the background.

6. 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 €317
includes taxes & fees
13 Nov - 14 Nov
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.

7. 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, (103 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 €235
includes taxes & fees
9 Nov - 10 Nov
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A two-story house with a front porch and a landscaped garden.

8. A Cozy Private Suite in a Country Home near New Paltz

A Cozy Private Suite in a Country Home near New Paltz
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is €122
includes taxes & fees
9 Nov - 10 Nov
A Cozy Private Suite in a Country Home near New Paltz
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

9. 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, (34 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 €186
includes taxes & fees
6 Dec - 7 Dec
Dream getaway apartment in the foot of Gunks Ridge
A two-story house with a porch, a table, and chairs outside.

10. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is €177
includes taxes & fees
11 Nov - 12 Nov
Historic Horse Barn Apartment in Goshen
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

11. 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 €256
includes taxes & fees
12 Nov - 13 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

12. 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 €381
includes taxes & fees
22 Nov - 23 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.

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 €477
includes taxes & fees
22 Nov - 23 Nov
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

14. 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 €201
includes taxes & fees
9 Nov - 10 Nov
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A room with a glass table and chairs, a flat-screen TV on the wall, and a view of a beach and buildings.

15. Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (41 reviews)
"Great location very walkable"
United States
Tim B.
The price is €213
includes taxes & fees
10 Nov - 11 Nov
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
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, (46 reviews)
"The house was in a perfect location! Host was very easy to communicate with!"
United States
Matthew
The price is €411
includes taxes & fees
10 Nov - 11 Nov
The DeVita House Est. 1900
A living room with a fireplace, a painting, shelves with decorative items, and a television.

17. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
The price is €326
includes taxes & fees
9 Nov - 10 Nov
Grant - A Tranquil One Bedroom Steps from River
An outdoor seating area with a fire pit, a wooden barrel structure, and a blue sofa.

18. Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful stay!"
United States
Bernice
The price is €248
includes taxes & fees
19 Nov - 20 Nov
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

19. 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 €205
includes taxes & fees
9 Nov - 10 Nov
Cabin in the heart of the Hudson Valley, Cabin 4
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

20. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
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."
United States
Theresa
The price is €175
includes taxes & fees
9 Nov - 10 Nov
Zen House at the Mountain Ridge
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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Find out more about Montgomery

Everything you need to know about Montgomery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery holiday rentals we have selected for you start as low as €122 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montgomery rentals

At Expedia, we put the best Montgomery holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montgomery rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.