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Montgomery Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Montgomery vacation rentals

Microwave, oven, stovetop, dishwasher

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)
"Was a great stay and fabulous communication! Highly recommend "
United States
Michael C.
The price is ￥24,117
￥46,770 total
includes taxes & fees
Sep 15 - Sep 16
Modern Hudson Valley Apt 202 - King/Queen/Twin
Exterior

2. 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 ￥16,393
￥32,423 total
includes taxes & fees
Sep 14 - Sep 15
Historic Cabin with Pool & Fire Pit
Property grounds

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

Lux Cabin on Farm, River, Animals, Projector
Montgomery
The price is ￥37,441
￥76,421 total
includes taxes & fees
Sep 16 - Sep 17
Lux Cabin on Farm, River, Animals, Projector
Coffee/tea maker, fridge, microwave, oven

4. 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 ￥125,336
￥217,558 total
includes taxes & fees
Sep 14 - Sep 15
New Farmhouse-Hot Tub, King Beds, Game Room, Pro Golf Sim & Amazing Valley View!
1 bedroom, desk, iron/ironing board, WiFi (free)

5. 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 ￥30,129
￥54,383 total
includes taxes & fees
Sep 14 - Sep 15
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Property grounds

6. 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.
The price is ￥30,298
￥63,372 total
includes taxes & fees
Sep 21 - Sep 22
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
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)
"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.
The price is ￥17,938
￥36,232 total
includes taxes & fees
Sep 14 - Sep 15
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Property grounds

8. 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 ￥41,089
￥88,544 total
includes taxes & fees
Sep 28 - Sep 29
Detox & Hike: Waterfront Oasis with Infrared Sauna & Shawangunk Mountains
Smart TV

9. 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 ￥22,827
￥44,973 total
includes taxes & fees
Sep 14 - Sep 15
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

10. Hudson Valley Group Getaway - 1.5hrs from NYC with Heated Pool, Hot Tub, Sauna!

Hudson Valley Group Getaway - 1.5hrs from NYC with Heated Pool, Hot Tub, Sauna!
Pine Bush
10.0 out of 10, Exceptional, (22 reviews)
"We stayed with Ilya for our third time and loved it again! Even with the Memorial Day rain we had a fantastic time in the house and the surrounding area. The pool is well heated and the kids even got in despite the 56 degree weather! We hope to stay again soon!"
United States
Elizabeth K.
The price is ￥191,650
￥381,558 total
includes taxes & fees
Oct 6 - Oct 7
Hudson Valley Group Getaway - 1.5hrs from NYC with Heated Pool, Hot Tub, Sauna!
Interior

11. 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 ￥14,983
￥30,300 total
includes taxes & fees
Sep 23 - Sep 24
Dream getaway apartment in the foot of Gunks Ridge
Design Apartment, Patio, Garden View | View from room

12. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is ￥51,308
￥63,173 total
includes taxes & fees
Oct 3 - Oct 4
Historic Horse Barn Apartment in Goshen
Smart TV

13. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (39 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is ￥22,998
￥67,829 total
includes taxes & fees
Sep 13 - Sep 14
The DeVita House Est. 1900
Suite | Desk, WiFi (free), individually furnished, bed sheets

14. Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.0 out of 10, (13 reviews)
"Room could have actually been cleaned , this is a building not a “hotel” ,"
United States
Jennifer
The price is ￥11,453
￥24,231 total
includes taxes & fees
Sep 13 - Sep 14
Cottage Suites
Property grounds

15. TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (18 reviews)
"Just what we were looking for"
United States
Natalya
The price is ￥20,146
￥35,616 total
includes taxes & fees
Sep 14 - Sep 15
TRANQUIL MOUNTAIN SOLITUDE
Outdoor dining

16. 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 ￥22,998
￥34,994 total
includes taxes & fees
Sep 16 - Sep 17
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Property grounds

17. Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Goshen
10.0 out of 10, Exceptional, (35 reviews)
"Great house, as advertised!"
United States
Steven K.
The price is ￥86,472
￥139,705 total
includes taxes & fees
Sep 23 - Sep 24
Renovated 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Terrace/patio

18. Riverfront stone cottage Private dock & boats Personal spa private resort

Riverfront stone cottage Private dock & boats Personal spa private resort
Gardiner
9.8 out of 10, Exceptional, (61 reviews)
"We had a great stay in this house, the host was very flexible and understanding, the house was clean and organized, loved the location "
United States
Paul T.
The price is ￥69,174
￥122,927 total
includes taxes & fees
Sep 28 - Sep 29
Riverfront stone cottage Private dock & boats Personal spa private resort
Outdoor spa tub

19. Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
9.8 out of 10, Exceptional, (66 reviews)
"We had a nice weekend at the Country House. I would recommend this property to friends and family. "
United States
Mike T.
The price is ￥50,442
￥88,343 total
includes taxes & fees
Sep 13 - Sep 14
Country House w/Hot Tub, Deck, Grill & Fire Pit
Smart TV

20. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (48 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 ￥20,698
￥45,269 total
includes taxes & fees
Sep 14 - Sep 15
Grant - A Tranquil One Bedroom Steps from River
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"Room was clean and comfortable. Breakfast was good and coffee was available 24rs a day in the lobby"
Kenneth 1-night trip
Posted 6 hours ago
Holiday Inn Express Poughkeepsie by IHG

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:

  • View our selection of featured holiday rentals in Montgomery
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  • Enter your travel dates to view the best deals on holiday rentals in Montgomery while they last

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?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Montgomery offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.