Woodstock Vacations from $836

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Your Woodstock Vacation

Enjoy unforgettable adventures when you reserve a vacation package to Woodstock. Whether you're a foodie, history buff or just a traveler who appreciates new places, there's something for everyone in this vibrant city. Be sure to do some sightseeing during your trip to Woodstock. Shagg Pond and Concord Pond are some favorite places to visit. That dream Woodstock vacation is just clicks away. Explore accommodations, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Woodstock vacation packages

Price found within the past 48 hours. Click for updated prices.
Pleasant Point Inn

Pleasant Point Inn

2 out of 5
Price was $847, price is now $836 per person
$836
per person
Dec 7 - Dec 10
found 19 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Auburn (LEW)
9.6/10 Exceptional! (5 reviews)
We had a wonderful stay at Pleasant Point Inn. The inn is located right on Kezar Lake, which is beautiful, particularly with the fall colors, and the view from our room was amazing. The food in the onsite restaurant was delicious , as was the complimentary breakfast. Everyone on staff was very helpful, with a special thank you to Holly who went out of her way to take care of any questions or requests that we had.

Reviewed on Oct 16, 2026

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Stay near popular Woodstock attractions

Concord Pond

Commune with nature and explore the great outdoors at Concord Pond during your travels in Woodstock.
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Woodstock Hotel Deals

Awesome unique home right on the lake with huge yard, hot tub near Sunday river

Awesome unique home right on the lake with huge yard, hot tub near Sunday river

Bryant pond ME
9/10 Wonderful! (35 reviews)
"I'd love to leave a better review, but that's difficult here.House is not air-conditioned as stated - there was one air conditioner sitting on the floor in a corner. No fans in most of the rooms, which all smelled very musty.Most of the beds/mattresses are terrible. I know it's "up to camp", but ..."

Reviewed on Jun 16, 2026

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Awesome unique home right on the lake with huge yard, hot tub near Sunday river
Getaway Lakefront Home for Skiing or Summer Enjoyment

Getaway Lakefront Home for Skiing or Summer Enjoyment

Bryant Pond ME
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Getaway Lakefront Home for Skiing or Summer Enjoyment
Mollyockett Motel & Swim Spa

Mollyockett Motel & Swim Spa

2 out of 5
1132 S Main St Bryant Pond ME
7.2/10 Good! (45 reviews)
"Great quiet place. Clean and comfy."

Reviewed on Mar 28, 2025

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Mollyockett Motel & Swim Spa
See all 1,135 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.

Find the Best Woodstock Vacation Packages

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
1,250
Top Sights
Concord Pond and Shagg Pond

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Frequently asked questions

How much does a Woodstock vacation package cost?
You'll find cheap prices from $836 on Expedia for your Woodstock getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Woodstock costs.
What are the cheapest months to go to Woodstock?
You can generally find reduced prices and better availability in October, November and December. Take a look at our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
Usually, a handful of days is enough to check out the top sights during your Woodstock vacation. But if you prefer to have time to chill out or go on day trips, consider extending your itinerary.
How to find the best Woodstock package deals?
Use Expedia's handy filters to find some unbeatable Woodstock package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Woodstock package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woodstock vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights separately. Better still, you can tailor your Woodstock getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Woodstock?
Secure fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Woodstock vacation.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Set off on your dream escape to Woodstock with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.