Holiday rentals near Harlem Valley Rail Trail
We found 581 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:26 Sept - 3 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
15% off
Price is NZ$8,143
NZ$8,143
NZ$1,163 per night
includes taxes & fees
Image gallery for The Hideaway: Berkshire Home - Village of Egremont
9.69.6 out of 10 rating
Exceptional
(23 reviews)
The Hideaway: Berkshire Home - Village of Egremont
Great Barrington, MA
16% off
Price is NZ$3,393
NZ$3,393
NZ$485 per night
includes taxes & fees
Image gallery for Country Studio in private setting
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Country Studio in private setting
Millbrook, NY
6% off
Price is NZ$2,096
NZ$2,096
NZ$299 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 NZ$2,234
NZ$2,234
NZ$319 per night
includes taxes & fees
Image gallery for Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
1010 out of 10 rating
Exceptional
(91 reviews)
Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Hillsdale, NY
9% off
Price is NZ$2,492
NZ$2,492
NZ$356 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
(20 reviews)
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Copake, NY
16% off
Price is NZ$2,527
NZ$2,527
NZ$361 per night
includes taxes & fees
Image gallery for Beautiful, Unique Country House w/Large Deck
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Beautiful, Unique Country House w/Large Deck
Hillsdale, NY
8% off
Price is NZ$2,661
NZ$2,661
NZ$380 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$2,873
NZ$2,873
NZ$410 per night
includes taxes & fees
Image gallery for Relax or be active! The choice is yours in this pet-friendly family home.
1010 out of 10 rating
Exceptional
(13 reviews)
Relax or be active! The choice is yours in this pet-friendly family home.
Norfolk, CT
7% off
Price is NZ$2,920
NZ$2,920
NZ$417 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(13 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is NZ$3,076
NZ$3,076
NZ$439 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 NZ$3,077
NZ$3,077
NZ$440 per night
includes taxes & fees
Image gallery for Charming Cottage, New Marlborough Village Green in the Berkshires
1010 out of 10 rating
Exceptional
(64 reviews)
Charming Cottage, New Marlborough Village Green in the Berkshires
Great Barrington, MA
8% off
Price is NZ$3,080
NZ$3,080
NZ$440 per night
includes taxes & fees
Image gallery for Captivating Artisan Built Home With Spectacular Water Views
1010 out of 10 rating
Exceptional
(111 reviews)
Captivating Artisan Built Home With Spectacular Water Views
Falls Village, CT
8% off
Price is NZ$3,108
NZ$3,108
NZ$444 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
(69 reviews)
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
Pine Plains, NY
8% off
Price is NZ$3,139
NZ$3,139
NZ$448 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$3,186
NZ$3,186
NZ$455 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 NZ$3,340
NZ$3,340
NZ$477 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$3,491
NZ$3,491
NZ$499 per night
includes taxes & fees
Image gallery for Cottage at Copake Lake
1010 out of 10 rating
Exceptional
(62 reviews)
Cottage at Copake Lake
Hillsdale, NY
8% off
Price is NZ$3,532
NZ$3,532
NZ$505 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 NZ$3,635
NZ$3,635
NZ$519 per night
includes taxes & fees
Image gallery for Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
Elizaville, New York
11% off
Price is NZ$3,800
NZ$3,800
NZ$543 per night
includes taxes & fees
Image gallery for Copake Lake rustic all-season 3 bdrm home
1010 out of 10 rating
Exceptional
(11 reviews)
Copake Lake rustic all-season 3 bdrm home
Hillsdale, NY
8% off
Price is NZ$3,905
NZ$3,905
NZ$558 per night
includes taxes & fees
Image gallery for Beautiful Period Home in the Berkshires
9.89.8 out of 10 rating
Exceptional
(38 reviews)
Beautiful Period Home in the Berkshires
South Egremont, MA
8% off
Price is NZ$3,998
NZ$3,998
NZ$571 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
(122 reviews)
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hillsdale, NY
16% off
Price is NZ$4,043
NZ$4,043
NZ$578 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 NZ$4,101
NZ$4,101
NZ$586 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Harlem Valley Rail Trail
Showing deals for: 22 Sept - 25 Sept
magical cabin in the woods
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is NZ$1,367
NZ$1,367
for 3 nights, 1 cabin
NZ$456 per night
includes taxes & fees
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)
The current price is NZ$1,834
NZ$1,834
for 3 nights, 1 cottage
NZ$611 per night
includes taxes & fees
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Sleeps 6 · 3 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is NZ$2,391
NZ$2,391
for 3 nights, 1 home
NZ$797 per night
includes taxes & fees
Lakefront Summer Spectacular in New England Just 2 Hours From NYC
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
The current price is NZ$2,133
NZ$2,133
for 3 nights, 1 home
NZ$711 per night
includes taxes & fees
Beautifully decorated & immaculate log chalet on 3 acres, winter views.
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
128 reviews(128 reviews)
The current price is NZ$1,347
NZ$1,347
for 3 nights, 1 chalet
NZ$449 per night
includes taxes & fees
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Sleeps 4 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is NZ$821
NZ$821
for 3 nights, 1 apartment
NZ$274 per night
includes taxes & fees
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
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