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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Montgomery vacation rentals

Exterior

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 ￥20,008
￥38,077 total
includes taxes & fees
Jul 22 - Jul 23
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, (20 reviews)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
The price is ￥28,423
￥53,945 total
includes taxes & fees
Jul 22 - Jul 23
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 ￥33,428
￥72,824 total
includes taxes & fees
Aug 12 - Aug 13
Lux Cabin on Farm, River, Animals, Projector
Coffee/tea maker, fridge, microwave, oven

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 ￥127,632
￥224,639 total
includes taxes & fees
Jul 22 - Jul 23
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
1 bedroom, desk, iron/ironing board, WiFi (free)

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, (4 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 ￥32,762
￥58,718 total
includes taxes & fees
Jul 22 - Jul 23
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
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 ￥18,526
￥35,447 total
includes taxes & fees
Aug 3 - Aug 4
Dream getaway apartment in the foot of Gunks Ridge
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, (88 reviews)
The price is ￥17,681
￥37,093 total
includes taxes & fees
Aug 4 - Aug 5
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is ￥26,796
￥51,223 total
includes taxes & fees
Aug 19 - Aug 20
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Property grounds

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, (59 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
The price is ￥30,528
￥65,131 total
includes taxes & fees
Aug 11 - Aug 12
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Suite | Desk, WiFi (free), individually furnished, bed sheets

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.0 out of 10, (8 reviews)
"It was a great place "
United States
Jose
The price is ￥15,676
￥29,684 total
includes taxes & fees
Jul 22 - Jul 23
Cottage Suites
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)
"This apartment was perfect for what we needed! Beautifully renovated, comfortable bed, and very close to Beacon! "
United States
Abby W.
The price is ￥21,939
￥47,799 total
includes taxes & fees
Aug 3 - Aug 4
Grant - A Tranquil One Bedroom Steps from River
Property grounds

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (11 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 ￥22,231
￥38,913 total
includes taxes & fees
Jul 28 - Jul 29
TRANQUIL MOUNTAIN SOLITUDE
Terrace/patio

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, (19 reviews)
"Clean, comfortable cabin near New Paltz. Great views, well stocked kitchen."
United States
Heather G.
The price is ￥38,071
￥57,540 total
includes taxes & fees
Jul 26 - Jul 27
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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 ￥20,950
￥32,422 total
includes taxes & fees
Aug 6 - Aug 7
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
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is ￥13,885
￥24,646 total
includes taxes & fees
Jul 27 - Jul 28
Glamping Tent & Campsite by Minnewaska State Park
1 bedroom, iron/ironing board, WiFi (free), 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 ￥28,420
￥54,674 total
includes taxes & fees
Jul 28 - Jul 29
Cozy country efficiency in the Hudson Valley
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 ￥19,298
￥33,501 total
includes taxes & fees
Jul 29 - Jul 30
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
1 bedroom, WiFi (free), bed sheets

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.6 out of 10, Exceptional, (31 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
The price is ￥21,193
￥36,632 total
includes taxes & fees
Aug 19 - Aug 20
Cozy Loft Cabin high above Bashakill Wildlife Refuge
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, (40 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is ￥19,285
￥33,661 total
includes taxes & fees
Jul 28 - Jul 29
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
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 ￥25,352
￥46,413 total
includes taxes & fees
Jul 22 - Jul 23
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"Once you get passed the smell of Marijuana, the place was comfortable."
James 1-night trip
Posted 1 hour ago
Sleep Inn & Suites 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 15 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.