Deals on vacations and trips to Pine Plains
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Pine Plains flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Eastwind Windham
Save 100% on your flight
Price was $1,422, price is now $1,116 per person
$1,116
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Save 100% on your flight
Price was $3,301, price is now $2,379 per person
$2,379
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay
Price was $17,228, price is now $12,573 per person
$12,573
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Houston (HOU) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. An outdoor pool and a terrace are also provided.
The Haüs Windham
Price was $1,825, price is now $1,384 per person
$1,384
per person
Jul 19 - Jul 26
found 20 hours ago
Roundtrip flight included
Houston (HOU) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A 24-hour gym and barbecue grills are also provided.
Perfect Family Vacation Home in the Mountains
Save 100% on your flight
Price was $2,692, price is now $2,134 per person
$2,134
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.
Top Pine Plains hotels deals
Inn at Pine Plains
3036 Church St. Pine Plains NY
$275 nightly
The price is $311 total per night
$311 total
May 3 - May 4
Total with taxes and fees
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.
Breakfast included
Pet friendly
Best Western Plus Kingston Hotel And Conference Center
503 Washington Ave Kingston NY
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $98 total per night
$98 total
May 6 - May 7
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a garden, and a grocery/convenience store are also offered.
Pet friendly
Parking included
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
$199 nightly
The price is $215 total per night
$215 total
May 5 - May 6
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Residence Inn by Marriott Kingston
800 Frank Sottile Boulevard Kingston NY
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $160 total per night
$160 total
May 10 - May 11
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Pet friendly
AutoCamp Catskills
882 NY-212 Saugerties NY
$170 nightly
The price is $191 total per night
$191 total
May 14 - May 15
Total with taxes and fees
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Pet friendly
Parking included
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $282 total per night
$282 total
May 3 - May 4
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Pet friendly
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.
Popular places to visit
Stissing Lake Park
Explore the great outdoors at Stissing Lake Park, a lovely green space in Pine Plains.
Gallatin Town Hall
Gallatin Town Hall is just one of the places to see in Pine Plains, so why not enjoy the other things to explore during your travels?
Thompson Pond
Commune with nature and explore the great outdoors at Thompson Pond during your travels in Pine Plains. Wander the lakeside in this romantic area.
Frequently asked questions
Photos of local treasures
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