A rustic barn surrounded by autumn foliage on a hillside.

Pine Plains Holidays

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  • Discover the most popular places to visit in Pine Plains

    The Stissing Center

    This restored historic venue hosts diverse performances from music to theatre in Pine Plains, New York. Immerse yourself in intimate cultural experiences where historic charm meets modern artistic expression.

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    Stissing Lake Park

    Stissing Lake Park offers a serene lakeside escape with clear waters perfect for swimming and fishing. Families gather at picnic areas surrounded by natural beauty, creating a peaceful retreat from everyday life.

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    Thompson Pond

    Rating: 8.0/10 (1 review)

    This 15,000-year-old glacial kettle pond offers a peaceful 2.7-mile trail through diverse ecosystems. Bring binoculars to spot some of the 160 bird species that inhabit this National Natural Landmark.

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    Gallatin Town Hall

    Gallatin Town Hall serves as the administrative heart of the community, hosting public meetings and town services. Monthly board meetings are held on the third Tuesday at 6:30 PM.

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    Pine Plains Library

    This welcoming community library offers diverse programmes and a rich collection. Enjoy comfortable reading areas and free Wi-Fi while exploring local history resources with help from knowledgeable staff.

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    Pine Plains Hotel Deals

    Inn at Pine Plains

    A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.
    • Address: 3036 Church St., Pine Plains, NY, 12567, US
    • Location: 0.2 mi from Pine Plains
    • Star rating: 3.5/5
    • Guest rating: 9.8/10 (Exceptional, 318 reviews)
    • Price: £195, includes taxes & fees, 23 Nov - 24 Nov
    • Review: good location/ walkable to down town !

    the Alander

    A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.
    • Address: 7519 NY-22, Copake, NY, 12516, US
    • Location: 9.1 mi from Pine Plains
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 292 reviews)
    • Price: £143, includes taxes & fees, 15 Nov - 16 Nov

    Jenny's Country Manor

    A vintage black car parked on a road with a white fence and trees in the background.
    • Address: 1639 Route 199, Red Hook, NY, 12581, US
    • Location: 4.8 mi from Pine Plains
    • Star rating: 2/5
    • Guest rating: 7.8/10 (Good, 144 reviews)
    • Price: £119, includes taxes & fees, 15 Nov - 16 Nov

    Holiday Inn Express & Suites Kingston-Ulster by IHG

    A buffet with various food items, including omelets and baked goods, served in metal containers.
    • Address: 1835 Ulster Avenue, Lake Katrine, NY, 12449, US
    • Location: 17.1 mi from Pine Plains
    • Star rating: 2.5/5
    • Guest rating: 9.4/10 (Exceptional, 1000 reviews)
    • Price: £96, includes taxes & fees, 13 Dec - 14 Dec

    Courtyard by Marriott Kingston

    An outdoor patio with a fire pit, seating, and a building in the background.
    • Address: 500 Frank Sottile Blvd, Kingston, NY, 12401, US
    • Location: 17 mi from Pine Plains
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 1004 reviews)
    • Price: £93, includes taxes & fees, 3 Dec - 4 Dec

    Beekman Arms and Delamater Inn

    A covered outdoor dining area with tables set for a meal, surrounded by columns and large windows.
    • Address: 6387 MILL ST, Rhinebeck, NY, 12572, US
    • Location: 13.7 mi from Pine Plains
    • Star rating: 3.5/5
    • Guest rating: 8.2/10 (Very good, 1001 reviews)
    • Price: £122, includes taxes & fees, 17 Nov - 18 Nov
    • Review: The side entry door for the Townsend rooms does not close properly and lock without some assistance. Staff very help and polite. Room was nice. Town was very quaint and has a few eateries to try.

    Hampton Inn Kingston

    A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.
    • Address: 1307 Ulster Ave, Kingston, NY, 12401, US
    • Location: 17.2 mi from Pine Plains
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 1000 reviews)
    • Price: £97, includes taxes & fees, 6 Dec - 7 Dec

    Rhinebeck Village Inn

    A row of metal chairs and a wooden barrel on a concrete floor against a wooden wall.
    • Address: 6260 Rt. 9, Rhinebeck, NY, 12572, US
    • Location: 13.6 mi from Pine Plains
    • Star rating: 2/5
    • Guest rating: 7.6/10 (Good, 484 reviews)
    • Price: £93, includes taxes & fees, 4 Dec - 5 Dec

    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.

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    Frequently Asked Questions

    How much does a Pine Plains travel package cost?

    Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Pine Plains from just . And the more you bundle, the more you save. Your dream holiday has never been more affordable.

    If I'm not able to travel, can I cancel my Pine Plains travel package?

    Because we understand life can be unpredictable, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

    How do I get a cheap travel package to Pine Plains?

    Our Pine Plains travel packages offer plenty of savings for the savvy wanderer. For the best deals, simply combine your hotel, flights and activities into a neat and tidy package. But great bargains are only the start of your next memorable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotels around the world to pick from. Whatever your budget, there's a travel package with your name on it.

    Does Expedia offer Book Now, Pay Later Pine Plains holidays?

    Yes, we do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits best during the checkout process and take the stress out of budgeting for your trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

    • Pay monthly holidays: Klarna has manageable monthly payment plans that suit all types of budgets, so you can book that well-deserved holiday now.
    • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip over multiple transactions.
    • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

    Where should I stay in Pine Plains?

    A getaway in Pine Plains wouldn't be complete without a visit to Thompson Pond. Why not book a hotel within walking distance of this fantastic tourist attraction?

    What are the top hotels in Pine Plains?

    Secure a room at HYATT house Fishkill/Poughkeepsie. It's one of this neighbourhood's most in-demand hotels. Another great option in Pine Plains is Hyatt Place Poughkeepsie.

    How far in advance should I book my Pine Plains holiday?

    Get rewarded with the biggest variety at the cheapest prices by booking your trip to Pine Plains early. Air carriers tend to advertise tickets anywhere up to 12 months before departure, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best bargains around, so it's never a bad time to book your dream holiday!

    What does an Expedia Pine Plains travel package include?

    From airfares and hotels to rental cars, Expedia can help you put together a Pine Plains package that's right for you. Heading away for a week or longer? Check out a hotel, flight and rental car bundle. If you're taking a quick break, a hotel and flight deal may suit you better. Experiences can also be added after you've booked. Our travel packages make it simple to save and plan.

    What should I know before booking a Pine Plains travel package?

    You'll land great savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything in one spot will make your trip planning easier. So why waste money or time? Whether you're organising a luxury city stay with your love or a low-cost family road trip, have a look at our travel packages today.

    Can I choose my airline with a Pine Plains Expedia travel package?

    You certainly can. We offer more than 550 airline partners globally, so choose the carrier that best fits your travel preferences.

    * Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.