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.
Hotel Vienna
Price was $732, price is now $629 per person
$629
per person
May 28 - Jun 1
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay
Save 100% on your flight
Price was $6,336, price is now $4,591 per person
$4,591
per person
May 28 - Jun 1
found 3 hours ago
Roundtrip flight included
Chicago (CHI) 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.
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House
Save 100% on your flight
Price was $1,981, price is now $1,517 per person
$1,517
per person
May 28 - Jun 1
found 3 hours ago
Roundtrip flight included
Chicago (CHI) 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.
The Haüs Windham
Price was $1,082, price is now $870 per person
$870
per person
May 28 - Jun 1
found 3 hours ago
Roundtrip flight included
Chicago (CHI) 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.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Save 100% on your flight
Price was $2,466, price is now $2,070 per person
$2,070
per person
May 28 - Jun 1
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to Hudson (HCC)
This chalet features a hot tub and a sauna. Free self parking and a terrace are also offered on site.
Top Pine Plains hotels deals
Inn at Pine Plains
3036 Church St. Pine Plains NY
$253 nightly
The price is $286 total per night
$286 total
May 4 - May 5
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 5 - May 6
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
$184 nightly
The price is $199 total per night
$199 total
May 27 - May 28
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 3 - May 4
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
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Free Cancellation
Reserve now, pay when you stay
$247 nightly
The price is $279 total per night
$279 total
Apr 29 - Apr 30
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
Quality Inn Hyde Park Poughkeepsie North
4142 Albany Post Rd Hyde Park NY
Free Cancellation
$93 nightly
The price is $105 total per night
$105 total
May 19 - May 20
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A computer station and a safe deposit box are also provided.
Breakfast included
Parking included
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.
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.
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?
Frequently asked questions
Photos of local treasures
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