Holiday rentals near Harlem Valley Rail Trail
We found 567 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:8 Aug - 15 Aug
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
16% off
Price is NZ$6,573
NZ$6,573
NZ$939 per night
includes taxes & fees
Image gallery for A BEAUTIFUL SALT WATER, HEATED POOL! THE PERFECT GET AWAY!
1010 out of 10 rating
Exceptional
(52 reviews)
A BEAUTIFUL SALT WATER, HEATED POOL! THE PERFECT GET AWAY!
Dover Plains, NY
16% off
Price is NZ$17,267
NZ$17,267
NZ$2,467 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(6 reviews)
Taghkanic Glass House
Hudson, NY
8% off
Price is NZ$58,284
NZ$58,284
NZ$8,326 per night
includes taxes & fees
Image gallery for Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
1010 out of 10 rating
Exceptional
(10 reviews)
Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
Millerton, NY
8% off
Price is NZ$3,663
NZ$3,663
NZ$523 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(9 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is NZ$3,100
NZ$3,100
NZ$443 per night
includes taxes & fees
Image gallery for Copake Lake home near cultural attractions Of The Berkshires
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Copake Lake home near cultural attractions Of The Berkshires
Hillsdale, NY
8% off
Price is NZ$3,907
NZ$3,907
NZ$558 per night
includes taxes & fees
Image gallery for A Fun Farmhouse Near Ski Butternut
1010 out of 10 rating
Exceptional
(37 reviews)
A Fun Farmhouse Near Ski Butternut
Great Barrington, MA
8% off
Price is NZ$7,521
NZ$7,521
NZ$1,074 per night
includes taxes & fees
Image gallery for Modern Glass House designed by renowned architect Thomas Phifer
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Modern Glass House designed by renowned architect Thomas Phifer
Hudson, NY
8% off
Price is NZ$7,650
NZ$7,650
NZ$1,093 per night
includes taxes & fees
Image gallery for Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
Pine Plains, NY
8% off
Price is NZ$3,163
NZ$3,163
NZ$452 per night
includes taxes & fees
Image gallery for Captivating Artisan Built Home With Spectacular Water Views
1010 out of 10 rating
Exceptional
(110 reviews)
Captivating Artisan Built Home With Spectacular Water Views
Falls Village, CT
8% off
Price is NZ$3,132
NZ$3,132
NZ$447 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
(11 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is NZ$5,254
NZ$5,254
NZ$751 per night
includes taxes & fees
Image gallery for An acclaimed photographers country estate, arts community, near private schools!
9.49.4 out of 10 rating
Exceptional
(22 reviews)
An acclaimed photographers country estate, arts community, near private schools!
Sharon, CT
16% off
Price is NZ$7,235
NZ$7,235
NZ$1,034 per night
includes taxes & fees
Image gallery for Taconic Hideaway – Fireplace, Fire Pit & Swimming
1010 out of 10 rating
Exceptional
(5 reviews)
Taconic Hideaway – Fireplace, Fire Pit & Swimming
Copake, NY
12% off
Price is NZ$4,482
NZ$4,482
NZ$640 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 NZ$9,172
NZ$9,172
NZ$1,310 per night
includes taxes & fees
Image gallery for Private Kent Getaway With Views, Pond & Pool
1010 out of 10 rating
Exceptional
(15 reviews)
Private Kent Getaway With Views, Pond & Pool
Kent, CT
8% off
Price is NZ$4,117
NZ$4,117
NZ$588 per night
includes taxes & fees
Image gallery for Perfect Vacation Get Away - Historical New Marlborough
9.49.4 out of 10 rating
Exceptional
(54 reviews)
Perfect Vacation Get Away - Historical New Marlborough
Great Barrington, MA
12% off
Price is NZ$2,433
NZ$2,433
NZ$348 per night
includes taxes & fees
Image gallery for Catamount, Zip Line, Private Setting, Book Now!
1010 out of 10 rating
Exceptional
(6 reviews)
Catamount, Zip Line, Private Setting, Book Now!
Great Barrington, Massachusetts
7% off
Price is NZ$8,690
NZ$8,690
NZ$1,241 per night
includes taxes & fees
Image gallery for Restored 19th century farmhouse apartment 1- charming farmland and town culture!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Restored 19th century farmhouse apartment 1- charming farmland and town culture!
Hudson, NY
8% off
Price is NZ$1,747
NZ$1,747
NZ$250 per night
includes taxes & fees
Image gallery for Guesthouse Cabin vacation rentals in Berkshire County
1010 out of 10 rating
Exceptional
(6 reviews)
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield, MA
8% off
Price is NZ$8,653
NZ$8,653
NZ$1,236 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 NZ$8,365
NZ$8,365
NZ$1,195 per night
includes taxes & fees
Image gallery for The Blue Elm - A Historic Berkshire Cottage
1010 out of 10 rating
Exceptional
(7 reviews)
The Blue Elm - A Historic Berkshire Cottage
Ashley Falls, MA
8% off
Price is NZ$2,850
NZ$2,850
NZ$407 per night
includes taxes & fees
Image gallery for Whitney by AvantStay | Private Berkshires Estate
8.28.2 out of 10 rating
Very good
(11 reviews)
Whitney by AvantStay | Private Berkshires Estate
Sheffield, MA
9% off
Price is NZ$6,413
NZ$6,413
NZ$916 per night
includes taxes & fees
Image gallery for Navywood - Cozy Hudson Valley Escape
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Navywood - Cozy Hudson Valley Escape
Elizaville, New York
11% off
Price is NZ$4,275
NZ$4,275
NZ$611 per night
includes taxes & fees
Image gallery for Rare, peaceful glamping, hot shower, mini golf near appalachian trail
1010 out of 10 rating
Exceptional
(5 reviews)
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains, NY
8% off
Price is NZ$2,346
NZ$2,346
NZ$335 per night
includes taxes & fees
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Find the best place to stay - Harlem Valley Rail Trail
Pet-friendly Cottage at Historic Millbrook Farm Estate
Sleeps 5 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Lakefront Spring Stunner in New England Just 2 Hours From NYC
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
68 reviews(68 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