Search Deals onPrattsville Vacation Packages
Prattsville Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham
Price was $662, price is now $545 per person
$545
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Save 100% on your flight
Price was $2,306, price is now $1,904 per person
$1,904
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Eastwind Windham
Price was $645, price is now $586 per person
$586
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Windham NY Escape
Price was $659, price is now $612 per person
$612
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Stay at this cabin in Hensonville. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
The best
Reviewed on Oct 6, 2025
The Haüs Windham
Price was $989, price is now $934 per person
$934
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
Prattsville Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Oct 1 - Thu, Oct 15
FLL
Fort Lauderdale - Hollywood Intl.
SWF
Stewart Intl.
$126 Roundtrip, found 3 hours ago
$126
Roundtrip
found 3 hours ago
Sat, Oct 3 - Sat, Oct 3
TPA
Tampa Intl.
SWF
Stewart Intl.
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Thu, Oct 15 - Sun, Oct 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 16 hours ago
$187
Roundtrip
found 16 hours ago
Sun, Nov 1 - Thu, Nov 5
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
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