Pine Plains Vacations

Book a Hotel + Flight or Car together to unlock savings

Discover the most popular places to visit in Pine Plains

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

Pine Plains Hotel 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 from Sep 30 to Oct 1
$311 total
Sep 30 - Oct 1
Total with taxes and fees
9.8/10 Exceptional! (293 reviews)
Quiet and comfortable
"Quoet amd comfortable room. Very clean, and staff were vety friendly. Breakfast was cold continental style. It included breakfast breads, fruit, and the fixings for a hard bolied egg, hummus and arugula sandwich. No hot food. Otherwise, it was a a good stay."

Reviewed on Sep 2, 2025

Inn at Pine Plains
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
$122 nightly
The price is $137 total per night from Oct 5 to Oct 6
$137 total
Oct 5 - Oct 6
Total with taxes and fees
7.6/10 Good! (1,015 reviews)
"Front desk clerk, excellent service and very pleasant and friendly."

Reviewed on Sep 15, 2025

Best Western Plus Kingston Hotel And Conference Center
Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

2.5 out of 5
4142 Albany Post Rd, Hyde Park, NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Oct 13 to Oct 14
$101 total
Oct 13 - Oct 14
Total with taxes and fees
8/10 Very Good! (1,027 reviews)
"Staffs are helpful and courteous."

Reviewed on Sep 22, 2025

Quality Inn Hyde Park Poughkeepsie North
See all 1,529 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.

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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?
November, December and January are the best times to search for cheap Pine Plains vacation packages. Opting to travel in quieter periods means you can typically find lower prices on hotels and flights.
How many days is enough for Pine Plains?
The ideal duration of your Pine Plains vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to hit all the top attractions and explore 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.
Does Expedia offer Book Now, Pay Later Pine Plains vacation packages?
Set off on your perfect escape to Pine Plains with our Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.