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
Save 100% on your flight
Price was $1,259, price is now $1,007 per person
$1,007
per person
Jun 20 - Jun 26
found 10 hours ago
Roundtrip non-stop flight included
St. Louis (STL) 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.
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
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 4 hours 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.
Eastwind Windham

Eastwind Windham

3.5 out of 5
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 4 hours 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.
Perfect Family Vacation Home in the Mountains

Perfect Family Vacation Home in the Mountains

2 out of 5
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 4 hours 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.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Save 100% on your flight
Price was $3,472, price is now $2,808 per person
$2,808
per person
Jun 6 - Jun 13
found 4 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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

Inn at Pine Plains

3.5 out of 5
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.
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
$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.
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
$184 nightly
The price is $199 total per night
$199 total
May 28 - May 29
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
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.
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
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 30 - May 1
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.
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
$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.
Don't see what you're looking for?
See all available properties in Pine Plains
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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

Stissing Lake Park

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

Stissing Lake Park

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.

Thompson Pond

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?
$1,007 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