Pine Plains Vacations from $609
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The Latest Pine Plains vacation packages
Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham
Price was $1,120, price is now $963 per person
$963
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
8.8/10 Excellent! (133 reviews)
El personal de recepcion fue muy atento y servicial. Nos encanto todas las amenidades del hotel y la energia del sitio. Definitavemente queremos volver.
Reviewed on Oct 26, 2026
Eastwind Windham
Price was $838, price is now $790 per person
$790
per person
Dec 10 - Dec 14
found 19 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.2/10 Wonderful! (122 reviews)
Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay.
Reviewed on Oct 20, 2026
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Pine Plains Hotel Deals
Inn at Pine Plains
3036 Church St. Pine Plains NY
$275 nightly
The price is $311 total per night from Nov 3 to Nov 4
$311 total
Nov 3 - Nov 4
Total with taxes and fees
9.8/10 Exceptional! (318 reviews)
"good location/ walkable to down town !"
Reviewed on Oct 1, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundable
$76 nightly
The price is $85 total per night from Nov 25 to Nov 26
$85 total
Nov 25 - Nov 26
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"This motel was exactly what we were looking for during our short stay. It was clean comfortable and easy to access. The bathroom toilet flushing mechanism was a bit slow/occasionally needed two flushes. There are train tracks behind the building and there is a train that will come by at night that ..."
Reviewed on Nov 1, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $191 total per night from Nov 9 to Nov 10
$191 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,013 reviews)
"Very beautiful and historic. The property and the town. A bit enchanting. Nice boutique, locally owned shops. Fees like you stepped back in time. The room in the courtyard, Courtyard Double, was huge. It had a kitchenette type area with microwave, coffee maker and refrigerator, sitting area with ..."
Reviewed on Nov 2, 2026
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.
Find the Best Pine Plains Vacation Packages
Pine Plains Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,350 |
Top Sights | Millbrook Vineyards and Winery, Wings Castle and Old Rhinebeck Aerodrome |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
