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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Montgomery vacation rentals

Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 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 ￥19,906
￥37,883 total
includes taxes & fees
Jul 14 - Jul 15
Historic Cabin with Pool & Fire Pit
Microwave, oven, stovetop, dishwasher

Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (19 reviews)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
The price is ￥28,278
￥53,303 total
includes taxes & fees
Jul 15 - Jul 16
Modern Hudson Valley Apt 202 - King/Queen/Twin
Property grounds

Lux Cabin on Farm, River, Animals, Projector

Lux Cabin on Farm, River, Animals, Projector
Montgomery
The price is ￥30,590
￥68,991 total
includes taxes & fees
Jul 14 - Jul 15
Lux Cabin on Farm, River, Animals, Projector
Fridge, microwave, oven, stovetop

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.
The price is ￥49,272
￥83,972 total
includes taxes & fees
Jul 14 - Jul 15
Luxury 3BR with King Beds in Montgomery Village
Fridge, microwave, oven, stovetop

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.
The price is ￥164,694
￥272,614 total
includes taxes & fees
Aug 10 - Aug 11
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
1 bedroom, desk, iron/ironing board, free WiFi

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, (3 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 ￥36,035
￥62,897 total
includes taxes & fees
Jul 26 - Jul 27
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (9 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is ￥22,118
￥38,714 total
includes taxes & fees
Jul 21 - Jul 22
TRANQUIL MOUNTAIN SOLITUDE
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is ￥21,827
￥45,909 total
includes taxes & fees
Aug 3 - Aug 4
Grant - A Tranquil One Bedroom Steps from River
Property grounds

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, (86 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is ￥19,426
￥38,962 total
includes taxes & fees
Jul 20 - Jul 21
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior

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, (29 reviews)
"Clean and quiet."
United States
Ted
The price is ￥13,132
￥28,880 total
includes taxes & fees
Jul 14 - Jul 15
Dream getaway apartment in the foot of Gunks Ridge
Interior

Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (20 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is ￥14,406
￥23,425 total
includes taxes & fees
Jul 14 - Jul 15
Trails Head Tiny House
Outdoor dining

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 ￥20,857
￥32,469 total
includes taxes & fees
Jul 14 - Jul 15
Cabin in the heart of the Hudson Valley, Cabin 4
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is ￥13,824
￥24,537 total
includes taxes & fees
Jul 14 - Jul 15
Glamping Tent & Campsite by Minnewaska State Park
Interior

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (113 reviews)
"Was very pet friendly. "
United States
Kevin
The price is ￥21,827
￥37,990 total
includes taxes & fees
Jul 16 - Jul 17
Trails Head Cabin
Interior

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 ￥19,630
￥34,485 total
includes taxes & fees
Jul 26 - Jul 27
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥32,013
￥53,476 total
includes taxes & fees
Jul 16 - Jul 17
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (71 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is ￥28,294
￥54,624 total
includes taxes & fees
Jul 20 - Jul 21
Cozy country efficiency in the Hudson Valley
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (39 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is ￥23,961
￥38,997 total
includes taxes & fees
Jul 28 - Jul 29
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
1 bedroom, free WiFi, bed sheets

The Studio at the Inn at High Falls

The Studio at the Inn at High Falls
High Falls
8.0 out of 10, Very Good, (38 reviews)
"I had a great stay here, it’s just as listed; simple but has everything that I needed, check in was easy, communication was good, and bed was comfortable!"
United States
Jamie M.
The price is ￥18,189
￥43,731 total
includes taxes & fees
Jul 19 - Jul 20
The Studio at the Inn at High Falls
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.8 out of 10, Exceptional, (11 reviews)
"Quiet and lovely for a solo adventure with my dog. "
United States
Darcie B.
The price is ￥25,222
￥46,176 total
includes taxes & fees
Jul 14 - Jul 15
Tiny Home, King Bed & Hot Tub, Unit B
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"It was great, I’d stay there again."
Drew 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Find out more about Montgomery

Search for holiday rentals in Montgomery on Expedia! You can easily find your home rentals, villas, holiday apartments in Montgomery using one of the methods below:

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Look no further and take a look at our great range of rental properties in Montgomery!

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?

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

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?

Orange County Arboretum and Thomas Bull Memorial Park are a couple of lovely local spots to get outside and enjoy nature. You’ll find favorite places to visit like LEGOLAND® New York and Woodbury Common Premium Outlets in the larger area.

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.