Holiday rentals near Harlem Valley Rail Trail
We found 583 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:10 Apr - 17 Apr
Image gallery for Two Bedroom Cottage Close To Town
9.49.4 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Two Bedroom Cottage Close To Town
Sharon
5% off
Price is AU$3,339
AU$3,339
for 7 nights, 1 cottage
AU$477 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)
Waterfront Cottage 10 Min From Great Barrington
New Marlborough
8% off
Price is AU$3,647
AU$3,647
for 7 nights, 1 cottage
AU$521 per night
includes taxes & fees
Image gallery for Fickle Fox Farm. It’s snow season! Lifts are open.
1010 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Fickle Fox Farm. It’s snow season! Lifts are open.
Canaan
11% off
Price is AU$4,006
AU$4,006
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
Image gallery for Orchard Hill - Large Family Estate
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Orchard Hill - Large Family Estate
Millbrook
12% off
Price is AU$22,224
AU$22,224
for 7 nights, 1 home
AU$3,175 per night
includes taxes & fees
Image gallery for TREEMENDOUS VIEWS COTTAGE
1010 out of 10, Exceptional, (24 reviews)
Exceptional
(24 reviews)
TREEMENDOUS VIEWS COTTAGE
Amenia
8% off
Price is AU$5,893
AU$5,893
for 7 nights, 1 room
AU$842 per night
includes taxes & fees
Image gallery for Cozy Log Cabin Retreat with Pool on 4 Acres
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Cozy Log Cabin Retreat with Pool on 4 Acres
North Canaan
7% off
Price is AU$3,284
AU$3,284
for 7 nights, 1 home
AU$469 per night
includes taxes & fees
Image gallery for Charming & Great Location!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Charming & Great Location!
Verbank
17% off
Price is AU$5,244
AU$5,244
for 7 nights, 1 cottage
AU$749 per night
includes taxes & fees
Image gallery for Be our guest at The Nest!
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Be our guest at The Nest!
Pleasant Valley
12% off
Price is AU$1,801
AU$1,801
for 7 nights, 1 apartment
AU$257 per night
includes taxes & fees
Image gallery for An In-Town Beauty with Late Checkout
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
An In-Town Beauty with Late Checkout
Great Barrington
12% off
Price is AU$4,502
AU$4,502
for 7 nights, 1 home
AU$643 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, Exceptional, (35 reviews)
Exceptional
(35 reviews)
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Craryville
7% off
Price is AU$2,112
AU$2,112
for 7 nights, 1 home
AU$302 per night
includes taxes & fees
Image gallery for Private modern home of six acres
9.89.8 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)
Private modern home of six acres
Clinton Corners
22% off
Price is AU$2,484
AU$2,484
for 7 nights, 1 home
AU$355 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington
8% off
Price is AU$6,311
AU$6,311
for 7 nights, 1 home
AU$902 per night
includes taxes & fees
Image gallery for Twin Island Lake House • Hot Tub
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Twin Island Lake House • Hot Tub
Pine Plains
8% off
Price is AU$4,399
AU$4,399
for 7 nights, 1 home
AU$628 per night
includes taxes & fees
Image gallery for Guesthouse Cabin vacation rentals in Berkshire County
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
15% off
Price is AU$5,280
AU$5,280
for 7 nights, 1 cabin
AU$754 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Sheffield
16% off
Price is AU$8,718
AU$8,718
for 7 nights, 1 home
AU$1,245 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield
8% off
Price is AU$6,478
AU$6,478
for 7 nights, 1 home
AU$925 per night
includes taxes & fees
Image gallery for Lovely Catskill Views, Close to Hudson, 5 minutes from Lake Taghkanic
1010 out of 10, Exceptional, (105 reviews)
Exceptional
(105 reviews)
Lovely Catskill Views, Close to Hudson, 5 minutes from Lake Taghkanic
Elizaville
13% off
Price is AU$5,851
AU$5,851
for 7 nights, 1 home
AU$836 per night
includes taxes & fees
Image gallery for Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.69.6 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Great Barrington
12% off
Price is AU$1,766
AU$1,766
for 7 nights, 1 apartment
AU$252 per night
includes taxes & fees
Image gallery for Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Sheffield
12% off
Price is AU$3,777
AU$3,777
for 7 nights, 1 home
AU$540 per night
includes taxes & fees
Image gallery for Modern Victorian Walk to Main Street
1010 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Modern Victorian Walk to Main Street
Great Barrington
15% off
Price is AU$4,689
AU$4,689
for 7 nights, 1 home
AU$670 per night
includes taxes & fees
Image gallery for Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Copake
8% off
Price is AU$2,374
AU$2,374
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
Image gallery for Hudson Valley Artist Sanctuary
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Hudson Valley Artist Sanctuary
Red Hook
8% off
Price is AU$3,912
AU$3,912
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Image gallery for Large Barn styled vacation home that fits groups with space to spare.
1010 out of 10, Exceptional, (72 reviews)
Exceptional
(72 reviews)
Large Barn styled vacation home that fits groups with space to spare.
Craryville
7% off
Price is AU$3,968
AU$3,968
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
Image gallery for WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
1010 out of 10, Exceptional, (183 reviews)
Exceptional
(183 reviews)
WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
Red Hook
8% off
Price is AU$2,518
AU$2,518
for 7 nights, 1 apartment
AU$360 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
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Villa
Chalet
Find the best place to stay - Harlem Valley Rail Trail
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
Sleeps 22 · 9 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
160 reviews(160 reviews)
The Farm at Hyde Park
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
89 reviews(89 reviews)
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
211 reviews(211 reviews)
Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
Sleeps 14 · 6 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Sleeps 2 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
86 reviews(86 reviews)
Exclusive luxurious Dutchess County Farmhouse new pool, spa and outdoor kitchen
Sleeps 10 · 5 bedrooms · 3+ bathrooms
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