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Montgomery Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Montgomery holiday rentals

A modern kitchen with stainless steel appliances, wooden cabinets, and a marble countertop.

1. 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)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
The price is NZ$519
includes taxes & fees
8 Sept - 9 Sept
Modern Hudson Valley Apt 202 - King/Queen/Twin
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

2. 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 NZ$361
includes taxes & fees
8 Sept - 9 Sept
Historic Cabin with Pool & Fire Pit
A person ascending a stone staircase with a wooden railing, leading to a cabin with a dark exterior and a wooden deck.

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

Lux Cabin on Farm, River, Animals, Projector
Montgomery
The price is NZ$852
includes taxes & fees
23 Sept - 24 Sept
Lux Cabin on Farm, River, Animals, Projector
A spacious living room with a sofa, armchairs, and a coffee table. A kitchen with modern appliances is visible in the background.

4. 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, (5 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 NZ$613
includes taxes & fees
15 Sept - 16 Sept
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.

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, (19 reviews)
"Beautiful home, attentive hosts, and the hot tub was great!"
United States
Kyle F.
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

6. 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, (99 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is NZ$394
includes taxes & fees
14 Sept - 15 Sept
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.

7. 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 NZ$267
includes taxes & fees
7 Sept - 8 Sept
Dream getaway apartment in the foot of Gunks Ridge
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

8. 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 NZ$701
includes taxes & fees
21 Sept - 22 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 view of the outside.

9. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.0 out of 10, (11 reviews)
"Room could have actually been cleaned , this is a building not a “hotel” ,"
United States
Jennifer
The price is NZ$260
includes taxes & fees
9 Sept - 10 Sept
Cottage Suites
A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

10. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is NZ$491
includes taxes & fees
12 Sept - 13 Sept
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A rustic cabin with a wooden barrel entrance, stone fire pit, and outdoor seating area surrounded by a forest.

11. 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
10.0 out of 10, Exceptional, (23 reviews)
"One of the best cabins I have been to with family, kids had great time and wife also loved the vibe. So clean and it feels like a home away from home 😊 highly recommend it for everyone, worth it! I am going go visit again with friend's for sure!! I would say everything u can think about is ten on ten ⭐️"
United States
Rahul
The price is NZ$495
includes taxes & fees
10 Sept - 11 Sept
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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, (47 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 NZ$506
includes taxes & fees
7 Sept - 8 Sept
Grant - A Tranquil One Bedroom Steps from River
An outdoor seating area with red chairs and a fire pit, surrounded by rocks and trees, with string lights overhead.

13. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (18 reviews)
"Just what we were looking for"
United States
Natalya
The price is NZ$393
includes taxes & fees
9 Sept - 10 Sept
TRANQUIL MOUNTAIN SOLITUDE
A forested area with a table and chairs on a wooden platform.

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

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.4 out of 10, Exceptional, (3 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is NZ$383
includes taxes & fees
15 Sept - 16 Sept
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A cozy living room with a stone fireplace, a sofa, and a coffee table.

15. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (16 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is NZ$326
includes taxes & fees
9 Sept - 10 Sept
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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, (38 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is NZ$760
includes taxes & fees
7 Sept - 8 Sept
The DeVita House Est. 1900
A modern living room with a fireplace, a dining area with a wooden table, and a large window with curtains.

17. Zen House at the Mountain Ridge

Zen House at the Mountain Ridge
Gardiner
9.8 out of 10, Exceptional, (8 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
The price is NZ$530
includes taxes & fees
16 Sept - 17 Sept
Zen House at the Mountain Ridge
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, (28 reviews)
"Pet-friendly and easily accessible."
United States
Brigitte
The price is NZ$386
includes taxes & fees
7 Sept - 8 Sept
Cabin in the heart of the Hudson Valley, Cabin 4
A cozy living room with a sofa, a dining table, and a bed.

19. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (74 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is NZ$594
includes taxes & fees
9 Sept - 10 Sept
Cozy country efficiency in the Hudson Valley
A fireplace with logs, a vase with flowers, and candles on a woven mat.

20. 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 NZ$281
includes taxes & fees
7 Sept - 8 Sept
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
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
"Great parking for our truck and trailer. Wifi was good which was helpful"
Terri 1-night trip
Posted 5 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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, 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 NZ$161 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?

The Studio at the Inn at High Falls: This holiday home rental outside of Montgomery is located in a rural location, and offers a garden, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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.