Two large silos, a barn, and a green field under a blue sky.

Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Montgomery vacation 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.
$267 nightly
The price is $307
Sep 27 - Sep 28
Total with taxes and fees
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, (4 reviews)
"Excellent location! Very clean and the hosts were quick to respond to communication. We would definitely stay here again. "
United States
Barbara M.
$491 nightly
The price is $502
Sep 28 - Sep 29
Total with taxes and fees
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.
$189 nightly
The price is $223
Sep 29 - Sep 30
Total with taxes and fees
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.

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

Lux Cabin on Farm, River, Animals, Projector
Montgomery
$427 nightly
The price is $487
Sep 30 - Oct 1
Total with taxes and fees
Lux Cabin on Farm, River, Animals, Projector
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.
$1,184 nightly
The price is $1,358
Sep 28 - Sep 29
Total with taxes and fees
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, (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.
$315 nightly
The price is $360
Oct 13 - Oct 14
Total with taxes and fees
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

7. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Hay Loft Apartment in Barn - Goshen
A fire pit with four Adirondack chairs arranged around it, set on a gravel surface with a lake and trees in the background.

8. 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, (100 reviews)
"We were very happy with the house and location, but what made it amazing was how great host was. Very accommodating and helpful with helping us out last minute. Would absolutely recommend working with this host again."
United States
Chris W.
$222 nightly
The price is $248
Sep 27 - Sep 28
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

9. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
$318 nightly
The price is $391
Oct 4 - Oct 5
Total with taxes and fees
Carriage House Apartment Goshen NY
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, (60 reviews)
"Had a wonderful time! Loved our stay at this beautiful river front property!"
United States
Debbie M.
$344 nightly
The price is $385
Oct 19 - Oct 20
Total with taxes and fees
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
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.

12. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.4 out of 10, Exceptional, (16 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
$281 nightly
The price is $293
Sep 27 - Sep 28
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
A cozy living room with a sofa, a coffee table with candles, and a fireplace.

13. 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.
$175 nightly
The price is $177
Sep 29 - Sep 30
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
A lakeside view with a picnic table and chairs, a grill, and a clear sky.

14. 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.
$493 nightly
The price is $552
Oct 8 - Oct 9
Total with taxes and fees
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
A rustic cabin with a wooden barrel entrance, stone fire pit, and outdoor seating area surrounded by a forest.

15. 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, (25 reviews)
"Perfect for a short get away"
United States
Darryl
$295 nightly
The price is $298
Sep 30 - Oct 1
Total with taxes and fees
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.

16. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (49 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.
$249 nightly
The price is $282
Sep 28 - Sep 29
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
A cozy living room with a sofa, a dining table, and a bed.

17. 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.
$299 nightly
The price is $353
Sep 25 - Sep 26
Total with taxes and fees
Cozy country efficiency in the Hudson Valley
A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

18. Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (15 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
$236 nightly
The price is $279
Sep 27 - Sep 28
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 3
A living room with a sofa, a coffee table, a wooden chair, a striped rug, and a wall-mounted wreath.

19. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (40 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
$395 nightly
The price is $442
Oct 5 - Oct 6
Total with taxes and fees
The DeVita House Est. 1900
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

20. 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, (15 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
$121 nightly
The price is $135
Sep 29 - Sep 30
Total with taxes and fees
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"I felt right at home! A quiet, very clean room with plenty of parking. Hotel is conveniently close to the highway entrance. I enjoyed my stay and the breakfast."
Elizabeth 1-night trip
Posted 1 hour ago
Sleep Inn & Suites Monroe - Woodbury

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Montgomery in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $93 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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, City Winery Hudson Valley and Highland Lakes State Park 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.