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.
Windham NY Escape

Windham NY Escape

3 out of 5
Price was $979, price is now $862 per person
$862
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
Luggage storage is available at this cabin. Take advantage of the free self parking.
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 $5,811, price is now $4,569 per person
$4,569
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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 $5,824, price is now $4,581 per person
$4,581
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Red Feather Lodge

Red Feather Lodge

3 out of 5
Save 100% on your flight
Price was $2,870, price is now $2,455 per person
$2,455
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hudson (HCC)
This vacation home features a seasonal outdoor pool and a hot tub. Enjoy the sauna and perks like free self parking and free WiFi. A picnic area is also provided.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,239, price is now $1,064 per person
$1,064
per person
Oct 23 - Oct 26
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) 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.

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
Aug 23 - Aug 24
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
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
$189 nightly
The price is $214 total per night
$214 total
Aug 20 - Aug 21
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
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
$229 nightly
The price is $247 total per night
$247 total
Sep 7 - Sep 8
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

2.5 out of 5
4142 Albany Post Rd Hyde Park NY
Free Cancellation
$85 nightly
The price is $96 total per night
$96 total
Sep 8 - Sep 9
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.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
$179 nightly
The price is $200 total per night
$200 total
Sep 17 - Sep 18
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.
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
$93 nightly
The price is $103 total per night
$103 total
Sep 8 - Sep 9
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
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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.

Stay near popular Pine Plains attractions

Stissing Lake Park

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

How much are vacation packages to Pine Plains?
$862 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

A rustic barn surrounded by autumn foliage on a hillside.
A snowy landscape with rolling hills and a partly cloudy sky.
A rural landscape with rolling hills, autumn-colored trees, and hay bales in a field.