Holiday rentals near Harlem Valley Rail Trail
We found 595 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:21 Nov - 28 Nov
Image gallery for Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
Elizaville, NY
11% off
Price is NZ$4,752
NZ$4,752
NZ$679 per night
includes taxes & fees
Image gallery for Charming cottage with lake access, wood burning fire place, and WiFi
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Charming cottage with lake access, wood burning fire place, and WiFi
Elizaville, NY
12% off
Price is NZ$2,625
NZ$2,625
NZ$375 per night
includes taxes & fees
Image gallery for Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY
Millbrook, NY
8% off
Price is NZ$7,065
NZ$7,065
NZ$1,009 per night
includes taxes & fees
Image gallery for A Country Lodge Straight Out of the Pages of a Great Novel
1010 out of 10 rating
Exceptional
(12 reviews)
A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains, NY
8% off
Price is NZ$12,463
NZ$12,463
NZ$1,780 per night
includes taxes & fees
Image gallery for Lakefront Fall Foliage in New England Just 2 Hours From NYC
1010 out of 10 rating
Exceptional
(78 reviews)
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Sharon, CT
8% off
Price is NZ$3,240
NZ$3,240
NZ$463 per night
includes taxes & fees
Image gallery for Mountain View Getaway
1010 out of 10 rating
Exceptional
(55 reviews)
Mountain View Getaway
West Cornwall, CT
8% off
Price is NZ$4,053
NZ$4,053
NZ$579 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(7 reviews)
Taghkanic Glass House
Hudson, NY
8% off
Price is NZ$60,783
NZ$60,783
NZ$8,683 per night
includes taxes & fees
Image gallery for Private Tudor style 5 bedroom home in country setting.
1010 out of 10 rating
Exceptional
(9 reviews)
Private Tudor style 5 bedroom home in country setting.
Millbrook, NY
11% off
Price is NZ$12,644
NZ$12,644
NZ$1,806 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(28 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
8% off
Price is NZ$20,388
NZ$20,388
NZ$2,913 per night
includes taxes & fees
Image gallery for Charming Cabin On Scenic Road
1010 out of 10 rating
Exceptional
(5 reviews)
Charming Cabin On Scenic Road
Great Barrington, MA
28% off
Price is NZ$96,272
NZ$96,272
NZ$13,753 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Charming Columbia County Farm House
Hillsdale, NY
8% off
Price is NZ$4,354
NZ$4,354
NZ$622 per night
includes taxes & fees
Image gallery for West Cornwall Cabin ~ 4 Mi to Covered Bridge!
9.69.6 out of 10 rating
Exceptional
(8 reviews)
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
West Cornwall, CT
7% off
Price is NZ$3,946
NZ$3,946
NZ$564 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$9,321
NZ$9,321
NZ$1,332 per night
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(54 reviews)
Stunning Renovated Victorian
Great Barrington, MA
12% off
Price is NZ$16,045
NZ$16,045
NZ$2,292 per night
includes taxes & fees
Image gallery for COUNTRY RETREAT WITH POOL 10 MN FROM KENT CT
1010 out of 10 rating
Exceptional
(5 reviews)
COUNTRY RETREAT WITH POOL 10 MN FROM KENT CT
Kent, CT
8% off
Price is NZ$9,299
NZ$9,299
NZ$1,328 per night
includes taxes & fees
Image gallery for Mid-Century Home Surrounded by Meadows
1010 out of 10 rating
Exceptional
(7 reviews)
Mid-Century Home Surrounded by Meadows
Pine Plains, NY
8% off
Price is NZ$7,890
NZ$7,890
NZ$1,127 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
8% off
Price is NZ$7,230
NZ$7,230
NZ$1,033 per night
includes taxes & fees
Image gallery for Fun Getaway Lakehouse in the Hudson Valley
1010 out of 10 rating
Exceptional
(15 reviews)
Fun Getaway Lakehouse in the Hudson Valley
Craryville, NY
12% off
Price is NZ$4,378
NZ$4,378
NZ$625 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
(23 reviews)
An acclaimed photographers country estate, arts community, near private schools!
Sharon, CT
16% off
Price is NZ$7,256
NZ$7,256
NZ$1,037 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
(97 reviews)
Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
Copake, NY
8% off
Price is NZ$11,427
NZ$11,427
NZ$1,632 per night
includes taxes & fees
Image gallery for 5 Minutes from Catamount Ski Area
9.09.0 out of 10 rating
Wonderful
(21 reviews)
5 Minutes from Catamount Ski Area
Great Barrington, MA
8% off
Price is NZ$3,232
NZ$3,232
NZ$462 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 NZ$9,728
NZ$9,728
NZ$1,390 per night
includes taxes & fees
Image gallery for TREEMENDOUS VIEWS COTTAGE
1010 out of 10 rating
Exceptional
(22 reviews)
TREEMENDOUS VIEWS COTTAGE
Amenia, NY
15% off
Price is NZ$5,625
NZ$5,625
NZ$804 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
7% off
Price is NZ$3,255
NZ$3,255
NZ$465 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Harlem Valley Rail Trail
Charming Columbia County Farm House
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Stunning views & charming spacious 4-BR home pool and fireplace in Copake Falls
Sleeps 12 · 4 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
House Nestled Bet Vineyards/Pool, Sauna and Spa
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Woodland A-Frame
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Newley Renovated Contemporary Hudson Home 3-bedrooms 120 Acres with pond
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Twin Island Lake House • Hot Tub
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
15 reviews(15 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