Photo by ViajandoconAna Rustrian
Montgomery holiday rentals
We found 663 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals near Montgomery, NY (MGJ-Orange County) that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, such as parking and air conditioning. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Montgomery, NY (MGJ-Orange County)
Showing deals for:5 Sept - 12 Sept
Image gallery for Beacon Retreat with Hudson River views and access to hiking trails and downtown!
1010 out of 10 rating
Exceptional
(29 reviews)
Beacon Retreat with Hudson River views and access to hiking trails and downtown!
Beacon, NY
8% off
Price is AU$14,813
AU$14,813
AU$2,116 per night
includes taxes & fees
Image gallery for NEW – 2 Side-by-Side Lake Homes Sleep 17 Pet Friendly 2 Private Docks -1 hr NYC
1010 out of 10 rating
Exceptional
(6 reviews)
NEW – 2 Side-by-Side Lake Homes Sleep 17 Pet Friendly 2 Private Docks -1 hr NYC
Monroe, NY
8% off
Price is AU$27,497
AU$27,497
AU$3,928 per night
includes taxes & fees
Image gallery for Private Home with Pool & Jacuzzi in the Hudson Valley
1010 out of 10 rating
Exceptional
(8 reviews)
Private Home with Pool & Jacuzzi in the Hudson Valley
Montgomery, NY
9% off
Price is AU$9,878
AU$9,878
AU$1,411 per night
includes taxes & fees
Image gallery for Mountain House Escape - 1 Hour from NYC
1010 out of 10 rating
Exceptional
(7 reviews)
Mountain House Escape - 1 Hour from NYC
Warwick, NY
12% off
Price is AU$17,552
AU$17,552
AU$2,507 per night
includes taxes & fees
Image gallery for The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
1010 out of 10 rating
Exceptional
(11 reviews)
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Harriman, NY
12% off
Price is AU$8,595
AU$8,595
AU$1,228 per night
includes taxes & fees
Image gallery for Majestic RiverView Estate - Breathtaking Views
1010 out of 10 rating
Exceptional
(5 reviews)
Majestic RiverView Estate - Breathtaking Views
Beacon, NY
8% off
Price is AU$18,292
AU$18,292
AU$2,613 per night
includes taxes & fees
Image gallery for Hudson Valley Oasis - Hot Tub, Fireplace, 50mi NYC
1010 out of 10 rating
Exceptional
(9 reviews)
Hudson Valley Oasis - Hot Tub, Fireplace, 50mi NYC
New Windsor, NY
9% off
Price is AU$10,391
AU$10,391
AU$1,484 per night
includes taxes & fees
Image gallery for Stunning historic Victorian house in Newburgh
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Stunning historic Victorian house in Newburgh
Newburgh, NY
20% off
Price is AU$7,702
AU$7,702
AU$1,100 per night
includes taxes & fees
Image gallery for Wildflower Lotus Farm a Luxurious 5bd Home w/ Pool, Firepit and more
1010 out of 10 rating
Exceptional
(6 reviews)
Wildflower Lotus Farm a Luxurious 5bd Home w/ Pool, Firepit and more
Gardiner, NY
8% off
Price is AU$16,753
AU$16,753
AU$2,393 per night
includes taxes & fees
Image gallery for PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit
1010 out of 10 rating
Exceptional
(10 reviews)
PRISCILLA'S HOMESTEAD: Authentic Private Estate with Pool Tennis FirePit
Middletown, NY
8% off
Price is AU$12,945
AU$12,945
AU$1,849 per night
includes taxes & fees
Image gallery for Blue Springs; secluded paradise bordering Minnewaska State Park
1010 out of 10 rating
Exceptional
(47 reviews)
Blue Springs; secluded paradise bordering Minnewaska State Park
Accord, NY
8% off
Price is AU$8,696
AU$8,696
AU$1,242 per night
includes taxes & fees
Image gallery for 1890's Log Cabin ~ 230 Acre Private Reserve ~ 150’ Waterfall ~ Hiking Trails
9.89.8 out of 10 rating
Exceptional
(21 reviews)
1890's Log Cabin ~ 230 Acre Private Reserve ~ 150’ Waterfall ~ Hiking Trails
Wallkill, NY
8% off
Price is AU$18,157
AU$18,157
AU$2,594 per night
includes taxes & fees
Image gallery for Huge house with amazing kitchen, near great hiking; great for groups!
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Huge house with amazing kitchen, near great hiking; great for groups!
Cragsmoor, NY
8% off
Price is AU$10,413
AU$10,413
AU$1,488 per night
includes taxes & fees
Image gallery for SKY, HIKE, STARGAZE, FOREST BATH, SWIM BY STREAM IN THE SHAWANGUNK MOUNTAIN
9.89.8 out of 10 rating
Exceptional
(15 reviews)
SKY, HIKE, STARGAZE, FOREST BATH, SWIM BY STREAM IN THE SHAWANGUNK MOUNTAIN
Wallkill, NY
20% off
Price is AU$3,078
AU$3,078
AU$440 per night
includes taxes & fees
Image gallery for Magnificent Modern Farmhouse
1010 out of 10 rating
Exceptional
(22 reviews)
Magnificent Modern Farmhouse
Mountain Dale, NY
8% off
Price is AU$14,474
AU$14,474
AU$2,068 per night
includes taxes & fees
Image gallery for LOG CABIN IN ZEN FOREST
1010 out of 10 rating
Exceptional
(28 reviews)
LOG CABIN IN ZEN FOREST
Wallkill, NY
8% off
Price is AU$4,142
AU$4,142
AU$592 per night
includes taxes & fees
Image gallery for Modern Comfort Meets Nature -Private Dock, Fire Pit & Detached Sleep Cabins
9.89.8 out of 10 rating
Exceptional
(62 reviews)
Modern Comfort Meets Nature -Private Dock, Fire Pit & Detached Sleep Cabins
Monroe, NY
8% off
Price is AU$11,957
AU$11,957
AU$1,708 per night
includes taxes & fees
Image gallery for Wooden Paradise in Catskills!!!!
1010 out of 10 rating
Exceptional
(14 reviews)
Wooden Paradise in Catskills!!!!
Rock Hill, NY
8% off
Price is AU$4,510
AU$4,510
AU$644 per night
includes taxes & fees
Image gallery for Cozy Cottage minutes to West Point
1010 out of 10 rating
Exceptional
(58 reviews)
Cozy Cottage minutes to West Point
Cornwall, NY
13% off
Price is AU$6,508
AU$6,508
AU$930 per night
includes taxes & fees
Image gallery for Luxury School House Retreat With Sauna & Pool- 1HR from NYC
1010 out of 10 rating
Exceptional
(13 reviews)
Luxury School House Retreat With Sauna & Pool- 1HR from NYC
New Hampton, NY
9% off
Price is AU$13,287
AU$13,287
AU$1,898 per night
includes taxes & fees
Image gallery for Peaceful and Stylish Upstate Retreat near Minnewaska, Inness and Arrowwood Farms
1010 out of 10 rating
Exceptional
(6 reviews)
Peaceful and Stylish Upstate Retreat near Minnewaska, Inness and Arrowwood Farms
Accord, NY
17% off
Price is AU$5,221
AU$5,221
AU$746 per night
includes taxes & fees
Image gallery for Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Milton, NY
16% off
Price is AU$3,916
AU$3,916
AU$559 per night
includes taxes & fees
Image gallery for Field of Boaz - A Contemporary Country Home. Perfect for the whole family!
1010 out of 10 rating
Exceptional
(21 reviews)
Field of Boaz - A Contemporary Country Home. Perfect for the whole family!
Walden, NY
10% off
Price is AU$8,846
AU$8,846
AU$1,264 per night
includes taxes & fees
Image gallery for Modern, Artsy, & Lofty Log Home
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Modern, Artsy, & Lofty Log Home
Wallkill, ny
21% off
Price is AU$12,801
AU$12,801
AU$1,829 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Montgomery
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Sleeps 3 · 1 bedroom · 1 bathroom
Hike & Fish: Outdoor Retreat Near Trails
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Fully furnished master king bedroom with it's own full bathroom
Sleeps 4 · 1 bedroom · 1 bathroom
The Lander Pied-à-terre - pet friendly apartment in Historic Newburgh.
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Green Haven House
Sleeps 6 · 5 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
1880's Farmhouse, W/Private stream & Hot Tub
Sleeps 23 · 8 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value