Pine Plains Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Pine Plains Hotel Deals

Inn at Pine Plains

Inn at Pine Plains

3.5 out of 5
3036 Church St., Pine Plains, NY
The price is CA $314 per night from Jul 20 to Jul 21
CA $314
CA $355 total
Jul 20 - Jul 21
includes taxes & fees
9.8/10 Exceptional! (287 reviews)
"It's a beautiful property! The staff did an excellent job making our stay perfect. Our rooms were lovely. Breakfast was delicious. Thanks for making our stay a wonderful experience."

Reviewed on Jun. 20, 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
The price is CA $179 per night from Jul 28 to Jul 29
CA $179
CA $201 total
Jul 28 - Jul 29
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"We had a great stay. Breakfast was a good with several options."

Reviewed on Jul. 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
The price is CA $110 per night from Aug 10 to Aug 11
CA $110
CA $125 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,017 reviews)
A decent overnight stay
"Hotel room was clean and property is well-located. Hallway carpets were older and lumpy/stretched - probably need replacing. Breakfast was good."

Reviewed on Jul. 15, 2025

Quality Inn Hyde Park Poughkeepsie North
See all 1,537 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.

All Inclusive Vacations

All Inclusive Vacations

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Family Vacations

Frequently asked questions

How much does a Pine Plains vacation package cost?
You'll find cheap prices on Expedia for your Pine Plains break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Pine Plains costs.
What are the cheapest months to go to Pine Plains?
February, March and April are the best times to search for cheap Pine Plains vacation packages. Choosing to travel in quieter periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for Pine Plains?
With a well-organized travel plan, you can easily tick off the top Pine Plains sights in a few days. But if you want to explore off the beaten track or take day trips, think about booking your Pine Plains vacation for longer.
How to find the best Pine Plains package deals?
Use Expedia's filter tool to help you find some tempting Pine Plains package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Pine Plains package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Pine Plains vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a personalized Pine Plains vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Pine Plains?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Pine Plains escape.
How to plan a trip to Pine Plains?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Pine Plains.
  2. Budget wisely: In addition to the cost of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Pine Plains.
  3. Decide how long to go away for: Now that you're more familiar with Pine Plains, you can figure out the right length of your vacation. Create a draft itinerary and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Pine Plains vacation package that brings all your bookings together.

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