Holiday rentals near Harlem Valley Rail Trail
We found 579 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:19 Sept - 26 Sept
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(9 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
12% off
Price is AU$6,927
AU$6,927
AU$990 per night
includes taxes & fees
Image gallery for Newly renovated charming home , Brand new chefs kitchen very comfortable home .
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is AU$4,415
AU$4,415
AU$631 per night
includes taxes & fees
Image gallery for Converted Berkshire schoolhouse on a quiet river
1010 out of 10 rating
Exceptional
(32 reviews)
Converted Berkshire schoolhouse on a quiet river
Great Barrington, MA
8% off
Price is AU$3,347
AU$3,347
AU$478 per night
includes taxes & fees
Image gallery for Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
1010 out of 10 rating
Exceptional
(63 reviews)
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
Great Barrington, MA
8% off
Price is AU$7,689
AU$7,689
AU$1,098 per night
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is AU$7,357
AU$7,357
AU$1,051 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
17% off
Price is AU$15,145
AU$15,145
AU$2,164 per night
includes taxes & fees
Image gallery for Gorgeous Sheffield Home in Heart of Berkshires
1010 out of 10 rating
Exceptional
(50 reviews)
Gorgeous Sheffield Home in Heart of Berkshires
Sheffield, MA
8% off
Price is AU$8,456
AU$8,456
AU$1,208 per night
includes taxes & fees
Image gallery for Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
1010 out of 10 rating
Exceptional
(15 reviews)
Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
Sharon, CT
8% off
Price is AU$10,561
AU$10,561
AU$1,509 per night
includes taxes & fees
Image gallery for Cozy Log Cabin Retreat with Pool on 4 Acres
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Cozy Log Cabin Retreat with Pool on 4 Acres
Canaan, CT
7% off
Price is AU$3,934
AU$3,934
AU$562 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(6 reviews)
Taghkanic Glass House
Hudson, NY
9% off
Price is AU$50,998
AU$50,998
AU$7,285 per night
includes taxes & fees
Image gallery for Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
1010 out of 10 rating
Exceptional
(49 reviews)
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Great Barrington, MA
8% off
Price is AU$20,442
AU$20,442
AU$2,920 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(11 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is AU$2,837
AU$2,837
AU$405 per night
includes taxes & fees
Image gallery for Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
1010 out of 10 rating
Exceptional
(120 reviews)
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hillsdale, NY
16% off
Price is AU$3,448
AU$3,448
AU$493 per night
includes taxes & fees
Image gallery for Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
1010 out of 10 rating
Exceptional
(5 reviews)
Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
Ancram, NY
8% off
Price is AU$3,981
AU$3,981
AU$569 per night
includes taxes & fees
Image gallery for TREEMENDOUS VIEWS COTTAGE
1010 out of 10 rating
Exceptional
(21 reviews)
TREEMENDOUS VIEWS COTTAGE
Amenia, NY
19% off
Price is AU$4,222
AU$4,222
AU$603 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$8,829
AU$8,829
AU$1,261 per night
includes taxes & fees
Image gallery for Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
Ancram, NY
12% off
Price is AU$6,787
AU$6,787
AU$970 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
5% off
Price is AU$4,814
AU$4,814
AU$688 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 rating
Exceptional
(19 reviews)
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Copake, NY
16% off
Price is AU$2,423
AU$2,423
AU$346 per night
includes taxes & fees
Image gallery for Waterfront Escape +dock +kayaks +firepit +fireplace +games
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Copake, NY
8% off
Price is AU$4,030
AU$4,030
AU$576 per night
includes taxes & fees
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
8% off
Price is AU$7,353
AU$7,353
AU$1,050 per night
includes taxes & fees
Image gallery for Hilltop Home on 10 acres w/ hot tub, fire-pit + solar
1010 out of 10 rating
Exceptional
(13 reviews)
Hilltop Home on 10 acres w/ hot tub, fire-pit + solar
Pine Plains, NY
8% off
Price is AU$5,467
AU$5,467
AU$781 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 AU$2,895
AU$2,895
AU$414 per night
includes taxes & fees
Image gallery for Pretty Farmhouse 4 bed/3.5 ba with Gorgeous Kitchen and Big Porch - close to GB!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Pretty Farmhouse 4 bed/3.5 ba with Gorgeous Kitchen and Big Porch - close to GB!
Great Barrington, MA
8% off
Price is AU$4,647
AU$4,647
AU$664 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
magical cabin in the woods
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 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)
Pet-friendly Cottage at Historic Millbrook Farm Estate
Sleeps 5 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Lovely cottage on quiet country road in Millerton, New York, on 23 acres.
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
11 reviews(11 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
14 reviews(14 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