Search Deals onPine Plains Vacation Packages
Pine Plains Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham
Save 100% on your flight
Price was $1,081, price is now $841 per person
$841
per person
Nov 20 - Nov 25
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.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain
Save 100% on your flight
Price was $7,527, price is now $5,547 per person
$5,547
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking, volleyball on site, and a pool table. Popular attractions Windham Mountain Resort and Hunter Mountain 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 $7,361, price is now $5,425 per person
$5,425
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Stay at this cottage in Hensonville. Enjoy free parking and air conditioning. Popular attractions Windham Mountain Resort and Hunter Mountain are located nearby.
Hotel Vienna
Price was $1,269, price is now $997 per person
$997
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Springfield (SPI) to Hudson (HCC)
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Eastwind Windham
Price was $1,037, price is now $871 per person
$871
per person
Nov 20 - Nov 25
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.
The restaurant was out of most dishes, not many other options. It’s ran by a small group of individuals so it’s hard to get a hold of people. Overall, the day was okay.
Reviewed on Oct 6, 2026
The Haüs Windham
Price was $1,090, price is now $954 per person
$954
per person
Nov 20 - Nov 25
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 a 24-hour fitness center. Popular attractions Windham Mountain Resort and Windham Country Club are located nearby.
Clean beautiful staff is fabulous kitchen is very well stocked for cooking. Good luck with your establishment thank you for the wonderful stay
Reviewed on Oct 7, 2026
Windham NY Escape
Price was $1,368, price is now $1,204 per person
$1,204
per person
Nov 20 - Nov 25
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
Pine Plains Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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