Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Montgomery vacation 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 CA $172
CA $325 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $220
CA $413 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $278
CA $439 total
includes taxes & fees
Nov 9 - Nov 10
Montgomery Village Center King Bed Ground Floor
A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

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 CA $845
CA $1,233 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $757
CA $1,422 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $369
CA $597 total
includes taxes & fees
Nov 13 - Nov 14
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, (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 CA $182
CA $375 total
includes taxes & fees
Nov 23 - Nov 24
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

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 CA $101
CA $187 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $127
CA $251 total
includes taxes & fees
Nov 8 - Nov 9
Dream getaway apartment in the foot of Gunks Ridge
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
9.4 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 CA $208
CA $396 total
includes taxes & fees
Nov 12 - Nov 13
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
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 CA $266
CA $328 total
includes taxes & fees
Nov 8 - Nov 9
Historic Horse Barn Apartment in Goshen
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 CA $287
CA $598 total
includes taxes & fees
Dec 7 - Dec 8
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 CA $346
CA $778 total
includes taxes & fees
Nov 9 - Nov 10
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
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
9.8 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 CA $210
CA $306 total
includes taxes & fees
Nov 8 - Nov 9
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

15. 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 CA $209
CA $311 total
includes taxes & fees
Nov 8 - Nov 9
Cabin in the heart of the Hudson Valley, Cabin 4
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 CA $245
CA $634 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $278
CA $504 total
includes taxes & fees
Nov 8 - Nov 9
Grant - A Tranquil One Bedroom Steps from River
A modern kitchen with a built-in microwave and a dining area with a table and chairs.

18. The Columbus Hotel - The Courtyard Suite - 89-303

The Columbus Hotel - The Courtyard Suite - 89-303
Middletown
The price is CA $143
CA $302 total
includes taxes & fees
Dec 8 - Dec 9
The Columbus Hotel - The Courtyard Suite - 89-303
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

19. 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 CA $237
CA $387 total
includes taxes & fees
Nov 8 - Nov 9
Cabin in the Heart of the Hudson Valley, Cabin 1
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 CA $151
CA $269 total
includes taxes & fees
Nov 9 - Nov 10
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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Top Montgomery Hotel Reviews

A buffet with various food items, including omelets and baked goods, served in metal trays.
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG
Montgomery

10/10 Excellent

The staff was great! The room was clean and the breakfast was excellent.
Canada
Joey
Reviewed January 12, 2026
Holiday Inn Express & Suites Montgomery by IHG

Find out more about Montgomery

Everything you need to know about Montgomery vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montgomery vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montgomery vacation rentals we have selected for you start as low as CA $100 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 vacation 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 vacation.

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 vacation rentals in Montgomery?

Yes, you can find vacation rentals in Montgomery near Orange County Arboretum, or you can choose a more secluded option if you're looking for extra privacy while you relax. Our travelers 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 vacation rentals that Montgomery has to offer?

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

How many vacation rentals are there in Montgomery?

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

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 vacation rental in Montgomery like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Montgomery. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.