Woodstock Vacations from $699

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Your Woodstock Vacation

Book a tailored Woodstock vacation package that includes only the things you need and nothing you don't. Great for families, festivals and markets, think about basing yourself in the neighborhood of Kingston Stockade District. If a sightseeing tour is part of the program during your trip to Woodstock, visit big attractions like Overlook Mountain Trailhead, Bethel Woods Museum and Opus 40. Don't put off visiting this destination any longer. The perfect Woodstock vacation is a couple of clicks away with Expedia.

The Latest Woodstock vacation packages

Price found within the past 48 hours. Click for updated prices.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Price was $926, price is now $699 per person
$699
per person
Nov 3 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9/10 Wonderful! (413 reviews)
It was good expensive overall, but they can do better

Reviewed on Aug 7, 2025

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Save 100% on your flight
Price was $5,626, price is now $3,989 per person
$3,989
per person
Nov 3 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
No reviews
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $1,702, price is now $1,273 per person
$1,273
per person
Nov 3 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9.6/10 Exceptional! (171 reviews)
We usually book an Airbnb when traveling upstate, but we opted for convenience this time around. This is truly a hidden gem. It is right off the main street but secluded enough to feel like you’re deep in the woods. The staff was welcoming and accommodating and the property was maintained. Kid and pet friendly are a plus too! Only thing, we didn’t know we had to request for someone to set up the pull out bed, so when we went to do it there were left over crumbs and wrappers. The mattress itself looked clean, but it just turned me off. 4 of us slept in one bed. Despite that, I would definitely stay there again!

Reviewed on Aug 30, 2025

Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $927, price is now $721 per person
$721
per person
Nov 3 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9.2/10 Wonderful! (269 reviews)
Very convenient to hiking trails. Staff very friendly and helpful

Reviewed on Aug 23, 2025

Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

Cortland by Avantstay Charming Heritage Estate w/ Private Lake & Pool

3.5 out of 5
Price was $1,489, price is now $1,174 per person
$1,174
per person
Nov 3 - Nov 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Hudson (HCC)
9/10 Wonderful! (2 reviews)
Fine, elegant, house. A great departure from one’s daily life. Great layout but could use more lighting. There were old quirks about the house but it made it more unique. Some doors don’t shut and will rattle when windows are open. Could use a griddle or larger pans/more baking sheets. The property is gorgeous and the crisp air was refreshing. Lovely experience and would book again!

Reviewed on Apr 7, 2024

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Discover the most popular places to visit in Woodstock

Overlook Mountain Trailhead

Learn about the local history of Woodstock when you take a trip to Overlook Mountain Trailhead. Discover the mountain views while you're in the area.

Overlook Mountain Trailhead

Karma Triyana Dharmachakra Monastery

Learn about the local history of Woodstock with a stop at Karma Triyana Dharmachakra Monastery. Discover the mountain views while you're in the area.

Karma Triyana Dharmachakra Monastery

Woodstock Music Shop

4/5(1 review)

You can search for that perfect souvenir at Woodstock Music Shop during your trip to Woodstock. Discover the mountain views while you're in the area.

Woodstock Music Shop

Woodstock Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
$313 nightly
The price is $346 total per night from Sep 2 to Sep 3
$346 total
Sep 2 - Sep 3
Total with taxes and fees
Woodstock Way Hotel
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street, Woodstock, NY
$199 nightly
The price is $223 total per night from Sep 8 to Sep 9
$223 total
Sep 8 - Sep 9
Total with taxes and fees
Morning Glory B n B Woodstock NY
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $246 total per night from Sep 8 to Sep 9
$246 total
Sep 8 - Sep 9
Total with taxes and fees
Hotel Dylan
See all 2,416 properties in Woodstock
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 Woodstock vacation package cost?
You can snap up a vacation package to this destination from $699 on Expedia. But how much your vacation to Woodstock costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Woodstock?
If you're hoping to book a cheap Woodstock vacation package, consider planning a trip in May, October and November. You'll typically find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Woodstock?
With about 2 days, you'll have enough time to experience popular neighborhoods like Zena and West Hurley during your Woodstock vacation. Remember to also add Woodstock Golf Club and Thorn Preserve - Catskill Center to your sightseeing list. Searching for more adventures? Consider venturing outside of Woodstock on day trips and tours.
Is it worth booking a vacation package to Woodstock?
Whether you'd like to explore key attractions like Overlook Mountain Trailhead and Karma Triyana Dharmachakra Monastery on your Woodstock vacation, or coming for its great markets, hiking and cycling, there's something for everyone here. With so many things to see and do, you'll soon learn why so many people think Woodstock is a good vacation destination.
How to find the best Woodstock package deals?
Bagging a cheap Woodstock package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Woodstock package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Woodstock vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Woodstock?
If you have your Woodstock vacation dates confirmed, book early to grab some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Woodstock?

  1. Choose when to go: Check your calendar and get your bags packed. Your favorite time of year and the activities on offer will also help you decide when to escape to Woodstock.
  2. Set a budget: Factor in costs like food, flights and transportation when calculating how much to save for your trip to Woodstock. Then, choose a property that fits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Discover Woodstock using our trip planning tool: Gain insights into the top attractions and best stays for your trip to Woodstock. You can also save your favorite locations, collaborate with family and friends and organize all your plans in one place.
  4. Set the duration of your trip: Start by listing all the activities and sights you'd like to get to in Woodstock. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Woodstock vacation package for you.
  6. Add on excursions and experiences: Have a look at our dedicated travel guide to find some awesome things to do in Woodstock. Book tickets or make reservations before you go to save time and avoid the stress of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Secure your dream trip to Woodstock with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up bargains before they sell out.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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