Pine Plains Trips (flight + hotel)

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    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
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    Plan, book, and manage your trip all in one place

Top hotels in Pine Plains

Inn at Pine Plains
Inn at Pine Plains
3.5 out of 5
3036 Church St., Pine Plains, NY
9.8/10 Exceptional! (285 reviews)
"Beautiful place. Accomadating staff. A lovely place to stay"

Reviewed on Jun 20, 2025

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Inn at Pine Plains
Beekman Arms Hotel
Beekman Arms Hotel
3.5 out of 5
6387 MILL ST, Rhinebeck, NY
8.2/10 Very Good! (719 reviews)
"Nice old inn and good breakfast"

Reviewed on Jun 19, 2025

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Beekman Arms Hotel
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
Fully refundableReserve now, pay when you stay
The price is P7,496 per night from Jun 29 to Jun 30
P7,496
P8,396 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"Great spot in Kingston, perfect for venturing into the Historic district, or driving over to Woodstock or the Catskills. Check-in took a while due to short staffing."

Reviewed on Jun 21, 2025

Best Western Plus Kingston Hotel And Conference Center
See all 1,518 properties in Pine Plains
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.

Frequently asked questions

How much does a Pine Plains vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Pine Plains costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Pine Plains?
You're likely to find lower rates and better availability in February, March and April. Browse our cheap Pine Plains vacation packages and you could get some great off-season deals.
How many days is enough for Pine Plains?
The ideal length for your Pine Plains vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
How to find the best Pine Plains package deals?
Start your search for a Pine Plains package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Pine Plains package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pine Plains adventure underway.
Is it cheaper to book a Pine Plains vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can customize your Pine Plains escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Pine Plains?
Enjoy incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Pine Plains getaway.
How to plan a trip to Pine Plains?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Pine Plains.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Pine Plains.
  3. Decide your trip length: Consider how much time you want to spend discovering Pine Plains. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Pine Plains vacation package.

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