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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Montgomery vacation rentals

Exterior

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 AED 393
AED 793 total
includes taxes & fees
9 Sep - 10 Sep
Historic Cabin with Pool & Fire Pit
Microwave, oven, stovetop, dishwasher

2. 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 AED 610
AED 1,141 total
includes taxes & fees
31 Aug - 1 Sep
Modern Hudson Valley Apt 202 - King/Queen/Twin
Property grounds

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

Lux Cabin on Farm, River, Animals, Projector
Montgomery
The price is AED 844
AED 1,786 total
includes taxes & fees
2 Sep - 3 Sep
Lux Cabin on Farm, River, Animals, Projector
Coffee/tea maker, fridge, microwave, oven

4. 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 AED 1,107
AED 1,920 total
includes taxes & fees
30 Aug - 31 Aug
Luxury 3BR with King Beds in Montgomery Village
Coffee/tea maker, fridge, microwave, oven

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, (19 reviews)
"Beautiful home, attentive hosts, and the hot tub was great!"
United States
Kyle F.
The price is AED 3,018
AED 5,246 total
includes taxes & fees
14 Sep - 15 Sep
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
1 bedroom, desk, iron/ironing board, WiFi (free)

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.
The price is AED 790
AED 1,408 total
includes taxes & fees
31 Aug - 1 Sep
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Property grounds

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, (99 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is AED 430
AED 880 total
includes taxes & fees
14 Sep - 15 Sep
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Interior

8. 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 AED 346
AED 720 total
includes taxes & fees
7 Sep - 8 Sep
Dream getaway apartment in the foot of Gunks Ridge
Suite | Desk, WiFi (free), individually furnished, bed sheets

9. Cottage Suites

Cottage Suites
3.0 star property
Middletown
5.4 out of 10, (10 reviews)
"Room could have actually been cleaned , this is a building not a “hotel” ,"
United States
Jennifer
The price is AED 245
AED 547 total
includes taxes & fees
1 Sep - 2 Sep
Cottage Suites
Smart TV

10. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is AED 545
AED 1,086 total
includes taxes & fees
4 Sep - 5 Sep
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Smart TV

11. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (47 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 AED 496
AED 1,093 total
includes taxes & fees
14 Sep - 15 Sep
Grant - A Tranquil One Bedroom Steps from River
Property grounds

12. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (17 reviews)
"Just what we were looking for"
United States
Natalya
The price is AED 526
AED 905 total
includes taxes & fees
8 Sep - 9 Sep
TRANQUIL MOUNTAIN SOLITUDE
Property grounds

13. 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 AED 314
AED 557 total
includes taxes & fees
1 Sep - 2 Sep
Glamping Tent & Campsite by Minnewaska State Park
Outdoor dining

14. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.4 out of 10, Exceptional, (3 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is AED 551
AED 850 total
includes taxes & fees
9 Sep - 10 Sep
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Property grounds

15. 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)
"We had a lovely time and the host had lots of great communication!"
United States
Amanda S.
The price is AED 777
AED 1,602 total
includes taxes & fees
21 Sep - 22 Sep
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
1 bedroom, WiFi (free), bed sheets

16. Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.6 out of 10, Exceptional, (32 reviews)
"This is a beautiful and quiet space to get away to and was just what I needed for the two nights."
United States
Dan V.
The price is AED 411
AED 768 total
includes taxes & fees
30 Aug - 31 Aug
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Smart TV

17. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (37 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is AED 551
AED 1,646 total
includes taxes & fees
31 Aug - 1 Sep
The DeVita House Est. 1900
Terrace/patio

18. 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
10.0 out of 10, Exceptional, (22 reviews)
"One of the best cabins I have been to with family, kids had great time and wife also loved the vibe. So clean and it feels like a home away from home 😊 highly recommend it for everyone, worth it! I am going go visit again with friend's for sure!! I would say everything u can think about is ten on ten ⭐️"
United States
Rahul
The price is AED 806
AED 1,254 total
includes taxes & fees
3 Sep - 4 Sep
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Apartment, 3 Bedrooms, Kitchen | Living area

19. 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
Fireplace, books

20. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (16 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is AED 483
AED 882 total
includes taxes & fees
21 Sep - 22 Sep
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

10/10 Excellent
"Good"
Arthur 1-night trip
Posted 1 hour ago
Spark by Hilton Fishkill

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 free WiFi 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?

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.