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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 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)
"Great hosts and great location!"
United States
Shelby A.
The price is AU$433
includes taxes & fees
26 Oct - 27 Oct
Modern Hudson Valley Apt 202 - King/Queen/Twin
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

2. 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 AU$765
includes taxes & fees
3 Nov - 4 Nov
Luxury 3BR with King Beds in Montgomery Village
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 AU$322
includes taxes & fees
3 Nov - 4 Nov
Historic Cabin with Pool & Fire Pit
A dining area with a wooden table and chairs, a painting on the wall, and a kitchen with white cabinets.

4. Montgomery Village Center King Bed Ground Floor

Montgomery Village Center King Bed Ground Floor
Montgomery
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 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 AU$476
includes taxes & fees
22 Oct - 23 Oct
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
A hallway with wooden flooring, white walls, a staircase with white railings, and a door at the end.

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 AU$1,179
includes taxes & fees
22 Oct - 23 Oct
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.

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 AU$2,106
includes taxes & fees
22 Oct - 23 Oct
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.

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 AU$392
includes taxes & fees
16 Nov - 17 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 AU$560
includes taxes & fees
2 Nov - 3 Nov
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

11. 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 AU$249
includes taxes & fees
22 Oct - 23 Oct
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.

12. 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 AU$206
includes taxes & fees
22 Oct - 23 Oct
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
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 AU$419
includes taxes & fees
1 Nov - 2 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A two-story house with a porch, a table, and chairs outside.

14. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is AU$375
includes taxes & fees
8 Nov - 9 Nov
Historic Horse Barn Apartment in Goshen
A lakeside view with a picnic table and chairs, a grill, and a clear sky.

15. 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 AU$735
includes taxes & fees
2 Nov - 3 Nov
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
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 AU$424
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, (43 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 AU$625
includes taxes & fees
27 Oct - 28 Oct
The DeVita House Est. 1900
An outdoor seating area with red chairs and a fire pit, surrounded by rocks and trees, with string lights overhead.

18. 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 AU$363
includes taxes & fees
27 Oct - 28 Oct
TRANQUIL MOUNTAIN SOLITUDE
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)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is AU$313
includes taxes & fees
26 Oct - 27 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A bathroom with a striped shower curtain, a toilet, a sink with a hairdryer, and a cabinet.

20. 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 AU$341
includes taxes & fees
27 Oct - 28 Oct
Cabin in the heart of the Hudson Valley, Cabin 4
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Will come back again!"
James 1-night trip
Posted 1 hour ago
Overlook Lodge at Bear Mountain

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 favourite 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 depend 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 AU$131 per night. Entering your travel dates in the search wizard might find you 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.