Holiday rentals near Harlem Valley Rail Trail
We found 587 holiday rentals — enter your dates for availability
Select the perfect private holiday rental within close proximity to Harlem Valley Rail Trail. Holiday rentals offer the best amenities for your family, friends or furry companion, such as air conditioning and Wi-Fi. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Harlem Valley Rail Trail
Showing deals for:3 Oct - 10 Oct
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is AU$8,344
AU$8,344
AU$1,192 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is AU$4,634
AU$4,634
AU$662 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(26 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is AU$8,856
AU$8,856
AU$1,265 per night
includes taxes & fees
Image gallery for Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
1010 out of 10 rating
Exceptional
(16 reviews)
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook, NY
8% off
Price is AU$3,486
AU$3,486
AU$498 per night
includes taxes & fees
Image gallery for Romantic and Secluded Berkshire's Gem
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Romantic and Secluded Berkshire's Gem
New Marlborough, MA
8% off
Price is AU$7,453
AU$7,453
AU$1,065 per night
includes taxes & fees
Image gallery for Konkapot Cottage, Pastoral Bliss With Wide Views
1010 out of 10 rating
Exceptional
(20 reviews)
Konkapot Cottage, Pastoral Bliss With Wide Views
New Marlborough, MA
8% off
Price is AU$3,763
AU$3,763
AU$538 per night
includes taxes & fees
Image gallery for Tower Hill - Hilltop Country Retreat with Panoramic Views
1010 out of 10 rating
Exceptional
(15 reviews)
Tower Hill - Hilltop Country Retreat with Panoramic Views
Millbrook, NY
8% off
Price is AU$10,373
AU$10,373
AU$1,482 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Charming Columbia County Farm House
Hillsdale, NY
8% off
Price is AU$2,866
AU$2,866
AU$409 per night
includes taxes & fees
Image gallery for Stunning Light-Filled Contemporary Home on 7 Acres
1010 out of 10 rating
Exceptional
(25 reviews)
Stunning Light-Filled Contemporary Home on 7 Acres
Salt Point, NY
22% off
Price is AU$5,396
AU$5,396
AU$771 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
New Marlborough, MA
16% off
Price is AU$8,696
AU$8,696
AU$1,242 per night
includes taxes & fees
Image gallery for Mountain View Getaway
1010 out of 10 rating
Exceptional
(54 reviews)
Mountain View Getaway
West Cornwall, CT
8% off
Price is AU$3,382
AU$3,382
AU$483 per night
includes taxes & fees
Image gallery for Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Cornwall Bridge, CT
8% off
Price is AU$8,327
AU$8,327
AU$1,190 per night
includes taxes & fees
Image gallery for Hudson Valley private 70's-style cabin on five acres, five minutes to town!
1010 out of 10 rating
Exceptional
(5 reviews)
Hudson Valley private 70's-style cabin on five acres, five minutes to town!
Millerton, NY
15% off
Price is AU$1,554
AU$1,554
AU$222 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10 rating
Exceptional
(35 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington, MA
8% off
Price is AU$6,420
AU$6,420
AU$917 per night
includes taxes & fees
Image gallery for Peacock Garden Cottage, A Unique Upstate Find
1010 out of 10 rating
Exceptional
(12 reviews)
Peacock Garden Cottage, A Unique Upstate Find
Pine Plains, NY
8% off
Price is AU$3,036
AU$3,036
AU$434 per night
includes taxes & fees
Image gallery for Superb Views -- Sunsets, Mountains, Valley
1010 out of 10 rating
Exceptional
(16 reviews)
Superb Views -- Sunsets, Mountains, Valley
Copake Falls, NY
16% off
Price is AU$3,534
AU$3,534
AU$505 per night
includes taxes & fees
Image gallery for COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.69.6 out of 10 rating
Exceptional
(27 reviews)
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Craryville, NY
8% off
Price is AU$2,055
AU$2,055
AU$294 per night
includes taxes & fees
Image gallery for A BEAUTIFUL SALT WATER, HEATED POOL! THE PERFECT GET AWAY!
1010 out of 10 rating
Exceptional
(53 reviews)
A BEAUTIFUL SALT WATER, HEATED POOL! THE PERFECT GET AWAY!
Dover Plains, NY
17% off
Price is AU$14,917
AU$14,917
AU$2,131 per night
includes taxes & fees
Image gallery for Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
Copake, NY
8% off
Price is AU$9,878
AU$9,878
AU$1,411 per night
includes taxes & fees
Image gallery for Beautiful Cottage and Waterfront Access
9.89.8 out of 10 rating
Exceptional
(104 reviews)
Beautiful Cottage and Waterfront Access
New Preston, CT
8% off
Price is AU$3,254
AU$3,254
AU$465 per night
includes taxes & fees
Image gallery for Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
1010 out of 10 rating
Exceptional
(13 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is AU$5,248
AU$5,248
AU$750 per night
includes taxes & fees
Image gallery for Log style home 4 miles to Catamount with fitness room
1010 out of 10 rating
Exceptional
(14 reviews)
Log style home 4 miles to Catamount with fitness room
Great Barrington, MA
6% off
Price is AU$5,244
AU$5,244
AU$749 per night
includes taxes & fees
Image gallery for Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Mountain View Farmhouse, pool/hot tub, fire pit, 4 seasons porch, game room
Millerton, NY
12% off
Price is AU$5,830
AU$5,830
AU$833 per night
includes taxes & fees
Image gallery for Berkshires dream house
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Berkshires dream house
Copake Falls, NY
8% off
Price is AU$4,069
AU$4,069
AU$581 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Harlem Valley Rail Trail
magical cabin in the woods
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Charming Columbia County Farm House
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Woodland A-Frame
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Pet-friendly Cottage at Historic Millbrook Farm Estate
Sleeps 5 · 3 bedrooms · 1+ bathroom
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Newley Renovated Contemporary Hudson Home 3-bedrooms 120 Acres with pond
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Top rated rentals - Harlem Valley Rail Trail
Comfortable cottage with helpful host 5 minute walk from centre of town
1010 out of 10
Exceptionalexceptional
13 reviews(13 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