Pine Plains Vacation Packages

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Top Pine Plains Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
per person
Jan. 24 - Jan. 27
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Hudson (HCC)
8.6/10 Excellent! (28 reviews)
Beautiful property with great amenities!

Reviewed on Nov. 6, 2024

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
per person
Jan. 24 - Jan. 27
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Hudson (HCC)
9.2/10 Wonderful! (540 reviews)
This place was so cute❤️

Reviewed on Dec. 13, 2024

Eastwind Windham

Eastwind Windham

2 out of 5
per person
Jan. 24 - Jan. 27
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Hudson (HCC)
9.4/10 Exceptional! (32 reviews)
This was a surprising find for us. We stayed in the main building and loved it. Jamie who checked us into our room was extremely helpful with suggestions. He doubles as the bar tender at night and we had a blast singing and sharing stories with him. Highly recommended this property. If you are lucky enough to interact with Jamie take it all in.

Reviewed on Nov. 30, 2024

Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
per person
Jan. 24 - Jan. 27
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Hudson (HCC)
9.2/10 Wonderful! (197 reviews)
The restaurant was excellent

Reviewed on Dec. 10, 2024

Maple Avenue by Summer A Hunter Mountain Retreat

Maple Avenue by Summer A Hunter Mountain Retreat

2 out of 5
per person
Jan. 24 - Jan. 27
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Hudson (HCC)
No reviews

Ready to book your vacation to Pine Plains?

 

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Pine Plains Hotel Deals

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 $176 per night from Jan. 5 to Jan. 6
CA $176
CA $197 total
includes taxes & fees
Jan 5 - Jan 6, 2025
7.8/10 Good! (1,001 reviews)
"Staff was professional, accommodating and helpful with restaurant suggestions."

Reviewed on Dec. 17, 2024

Best Western Plus Kingston Hotel And Conference Center
AutoCamp Catskills
AutoCamp Catskills
5 out of 5
882 NY-212, Saugerties, NY
Fully refundableReserve now, pay when you stay
The price is CA $271 per night from Jan. 5 to Jan. 6
CA $271
CA $354 total
includes taxes & fees
Jan 5 - Jan 6, 2025
9/10 Wonderful! (336 reviews)
"Overall nice Loved the love music in the evening and staff is friendly and helpful. but a few things to consider for the property management: 1) clubhouse is a little cold. People are wearing their coats in the clubhouse. Maybe consider increasing the heat 2) free breakfast is basically coffee, some ..."

Reviewed on Dec. 15, 2024

AutoCamp Catskills
Hampton Inn Kingston
Hampton Inn Kingston
2.5 out of 5
1307 Ulster Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jan. 5 to Jan. 6
CA $157
CA $176 total
includes taxes & fees
Jan 5 - Jan 6, 2025
9/10 Wonderful! (1,001 reviews)
Very good experience!
"The room was clean the staff was friendly. The hot breakfast was more than I thought it would be and had something for everyone."

Reviewed on Dec. 21, 2024

Hampton Inn Kingston
See all 1,499 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Pine Plains vacation package cost?
Offering great value package deals from CA $795 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.