Vacations Close To Harlem Valley Rail Trail

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Harlem Valley Rail Trail Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $1,035, price is now $855 per person
$855
per person
Aug 28 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Hotel Vienna is awesome! Family Friendly.. pet friendly…. Staff great! Fun to have Suana this time with pool… miss not having the hot tub…. 💙李💜❤️

Reviewed on Jul 11, 2026

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $4,016, price is now $3,027 per person
$3,027
per person
Aug 24 - Aug 30
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $9,260, price is now $7,039 per person
$7,039
per person
Aug 28 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,588, price is now $1,308 per person
$1,308
per person
Aug 28 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,667, price is now $1,405 per person
$1,405
per person
Aug 28 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Everything

Reviewed on Jul 12, 2026

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Price was $4,247, price is now $3,741 per person
$3,741
per person
Aug 28 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Christiansted (STX) to Hudson (HCC)

Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $1,291, price is now $1,167 per person
$1,167
per person
Aug 28 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Great!

Reviewed on Jul 7, 2026

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $7,885, price is now $5,892 per person
$5,892
per person
Aug 29 - Sep 3
found 1 hour ago
Roundtrip flight included
Christiansted (STX) to Hudson (HCC)

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Best Lodging Options Near Harlem Valley Rail Trail

Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 out of 5
74 Interlaken Road Lakeville CT
5.47 km from Harlem Valley Rail Trail
Book a stay at this spa hotel in Lakeville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Holley-Williams House Museum and Harney and ...
Troutbeck

Troutbeck

5 out of 5
515 Leedsville Rd Amenia NY
11.43 km from Harlem Valley Rail Trail
Book a stay at this luxury hotel in Amenia. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Amenia Free Library and TriArts Sharon ...
the Alander

the Alander

2.5 out of 5
7519 NY-22 Copake NY
14.18 km from Harlem Valley Rail Trail
Stay at this lodge in Copake. Enjoy free WiFi, free parking, and rainfall showerheads. Our guests praise the helpful staff in our reviews. Popular attractions ...
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3 out of 5
131 East Canaan Road East Canaan CT
18.47 km from Harlem Valley Rail Trail
Stay at this B&B in East Canaan. Enjoy free breakfast, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...
Little Cat Lodge

Little Cat Lodge

2 out of 5
37 Catamount Rd Copake Falls NY
24.12 km from Harlem Valley Rail Trail
Stay at this hotel in Copake Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Catamount Ski Area and Catamount Aerial Adventure ...
Blackberry River Inn

Blackberry River Inn

3 out of 5
538 Greenwoods Rd W Norfolk CT
23.24 km from Harlem Valley Rail Trail
Stay at this B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Haystack ...
Prospect Berkshires

Prospect Berkshires

3 out of 5
50 Prospect Lake Rd Egremont MA
27.01 km from Harlem Valley Rail Trail
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
The Harlow House

The Harlow House

2 out of 5
439 Lake Dr Rhinebeck NY
25.6 km from Harlem Valley Rail Trail
Stay at this guesthouse in Rhinebeck. Enjoy free WiFi, free parking, and a garden. Popular attractions Northern Dutchess Botanical Gardens and Center for Performing ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.