Woodstock Vacations

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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.

Discover the most popular places to visit in Woodstock

Shagg Pond

Commune with nature and explore the great outdoors at Shagg Pond during your travels in Woodstock. Stroll along the riverfront or experience the area's festivals.

Shagg Pond

Mineral Collector

3/5(1 review)

Enjoy an outing to Mineral Collector during your stay in Woodstock. Stroll along the riverfront or discover the mountain views in this relaxing area.

Mineral Collector

Woodstock Hotel Deals

New Chalet, Outdoor Dome w/views, Lakes, Hottub, Firepit, Arcade, Wet Bar, Pets

New Chalet, Outdoor Dome w/views, Lakes, Hottub, Firepit, Arcade, Wet Bar, Pets

Woodstock ME
10/10 Exceptional! (14 reviews)
"We booked this home for a quick last minute ski trip. Was absolutely fantastic and as advertised. The home was very clean and well taken care of and the igloo and hot tub were a big hit with the kids. The owner Fred was very responsive with any questions we had. Would definitely go back!"

Reviewed on Feb 21, 2026

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New Chalet, Outdoor Dome w/views, Lakes, Hottub, Firepit, Arcade, Wet Bar, Pets
Private Romantic Luxury Yurt- Sunset deck with Mt Views-Hot Tub-AC-WiFi-Fire Pit

Private Romantic Luxury Yurt- Sunset deck with Mt Views-Hot Tub-AC-WiFi-Fire Pit

Woodstock ME
10/10 Exceptional! (22 reviews)
"My spouse and senior pup stayed for three nights and got to experience both heavy rains and bright, sunny weather at the yurt! The rain was so soothing and the day spent on the deck in the sunshine was perfect. The hot tub is so nice to sit in under the stars! We really appreciated the attention ..."

Reviewed on May 19, 2026

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Private Romantic Luxury Yurt- Sunset deck with Mt Views-Hot Tub-AC-WiFi-Fire Pit
Mollyockett Motel & Swim Spa

Mollyockett Motel & Swim Spa

2 out of 5
1132 S Main St Bryant Pond ME
$133 nightly
The price is $145 total per night from Jun 21 to Jun 22
$145 total
Jun 21 - Jun 22
Total with taxes and fees
7.2/10 Good! (45 reviews)
"Great quiet place. Clean and comfy."

Reviewed on Mar 28, 2025

Mollyockett Motel & Swim Spa
See all 956 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 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.