Search Deals onCraryville Vacation Packages
Craryville Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Windham NY Escape
Price was $721, price is now $662 per person
$662
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Hudson (HCC)
Stay at this cabin in Hensonville. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
The best
Reviewed on Oct 6, 2025
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $8,857, price is now $7,106 per person
$7,106
per person
Oct 7 - Oct 12
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain
Save 100% on your flight
Price was $8,483, price is now $6,815 per person
$6,815
per person
Oct 7 - Oct 12
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Hunter Mountain and Windham Mountain Resort are located nearby.
The Haüs Windham
Price was $972, price is now $898 per person
$898
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up for all the inconveniences.
Reviewed on Aug 13, 2026
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Price was $1,835, price is now $1,817 per person
$1,817
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Hudson (HCC)
Book a stay at this business-friendly cottage in Windham. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Windham Country Club and Windham Vineyards and Winery are located nearby.
Craryville Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $8,857, price is now $7,106 per person
$7,106
per person
Oct 7 - Oct 12
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Hudson (HCC)
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