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.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $543, price is now $441 per person
$441
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Fort Walton Beach (VPS) 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.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $4,864, price is now $3,836 per person
$3,836
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Fort Walton Beach (VPS) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $4,877, price is now $3,848 per person
$3,848
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Fort Walton Beach (VPS) to Hudson (HCC)
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

3 out of 5
Save 100% on your flight
Price was $5,612, price is now $4,472 per person
$4,472
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Fort Walton Beach (VPS) 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.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $802, price is now $656 per person
$656
per person
Jul 27 - Jul 30
found 2 days ago
Roundtrip flight included
Fort Walton Beach (VPS) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.

Top Pine Plains hotels deals

Inn at Pine Plains

Inn at Pine Plains

3.5 out of 5
3036 Church St. Pine Plains NY
$275 nightly
The price is $311 total per night
$311 total
Jun 11 - Jun 12
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

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $125 total per night
$125 total
Jun 10 - Jun 11
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$201 nightly
The price is $217 total per night
$217 total
Jul 8 - Jul 9
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
$94 nightly
The price is $105 total per night
$105 total
Jun 14 - Jun 15
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$184 nightly
The price is $206 total per night
$206 total
Jul 9 - Jul 10
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

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
$279 nightly
The price is $316 total per night
$316 total
Jun 11 - Jun 12
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
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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

Thompson Pond

Commune with nature and explore the great outdoors at Thompson Pond during your travels in Pine Plains. Wander the lakeside in this relaxing area.

Thompson Pond

Stissing Lake Park

Explore the great outdoors at Stissing Lake Park, a lovely green space in Pine Plains.

Stissing Lake Park

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?

Gallatin Town Hall

Frequently asked questions

How much are vacation packages to Pine Plains?
$441 is all you need to spend for an amazing escape in Pine Plains. Bundle your flights and hotel into a Travelocity package and watch all the savings start to pile up. With prices this good, you'll want to start packing your suitcase now!
How long should my Pine Plains vacation be?
Most people spend roughly 2 nights in Pine Plains, but how long you stay is ultimately up to you. If you'd like to discover all the exciting things this place has to offer, why not hang around for a few extra nights?
Where can I get the best vacation package deals for Pine Plains?
Travelocity is the place to go to score a sensational Pine Plains package deal. Choose from 400 air carriers and 1,000,000 properties all over the world and put together a vacation package that fits your style. With so many options, it's easy to organize your next big escape.
Why should I purchase my Pine Plains vacation bundle with Travelocity?
You'll not only save lots, but you can also access our round-the-clock support, quality service and a Price Match Guarantee. Explore every nook-and-cranny across the globe, uncover lesser-known sights and create unforgettable memories — we'll take care of the important details.
Can I save on my Pine Plains car rental if I combine it with my hotel or flight?
You most certainly can — combine your car, hotel and flight into a Pine Plains vacation package and you can save loads. With so many places to explore in the Pine Plains area, having your own ride will make exploring easy. Once you've buckled yourself in, turn up the tunes and cruise toward Times Square, a renowned sight roughly 85 mi from Pine Plains.
Which airport is best for Pine Plains?
Bradley Intl. Airport (BDL), around 50 mi east of inner Pine Plains, is likely to be where you'll land. Your other options are Albany Intl. Airport (ALB) (55 mi away from central Pine Plains) and Stewart Intl. Airport (SWF) (40 mi away from central Pine Plains).
Where should I stay when visiting Pine Plains?
The Inn At Pine Plains is recommended by many travelers. Book soon before it's too late.

Photos of local treasures

Browse Pine Plains vacation photos for more inspiration

Sharon Ct, USA Fall foliage and autumn colors.
Snow Hillside Overlooking the Hudson Valley, Pine Plains, New York
Streaming Clouds Over a Hudson Valley Landscape