Woodstock Vacations from $983
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Your Woodstock Vacation
Prepare to experience Woodstock on your terms with a custom Woodstock vacation package! Uncovering the best parts of this interesting city is simple with a base in a neighborhood such as Killingly, which is good for nature, among other things. Every trip to Woodstock needs a well-thought-out itinerary. Fill yours with famous sights like Taylor Brooke Winery, Little River Plaza Shopping Center and Harrisville Golf Course. Don't delay visiting this destination any longer. The perfect Woodstock vacation is only a few clicks away with Expedia.
The Latest Woodstock vacation packages
Price found within the past 48 hours. Click for updated prices.
Pleasant View Inn
Misquamicut
$986
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Providence (PVD)
8.2/10 Very Good! (1,010 reviews)
It would’ve been very helpful had there been a microwave in the room for warming up food.
Not ONCE did anyone come to bring fresh towels or t paper, we had to go ask for the items to be brought to the room. However there’s a card on the nightstand to tip housekeeping, ?
Reviewed on Aug 22, 2026
Stay near popular Woodstock attractions
Roseland Cottage
This Gothic Revival pink mansion showcases Victorian opulence with original stained glass and elaborate wall coverings. Explore America's oldest indoor bowling alley after strolling through the formal boxwood gardens.
Taylor Brooke Winery
This boutique vineyard crafts small-batch wines from estate-grown grapes in Connecticut's scenic "Quiet Corner." Savor wine flights under the covered pavilion while enjoying vineyard views and occasional live music.
Roseland Park Golf Course
This historic 9-hole course from 1896 offers tree-lined fairways and challenging small greens. Enjoy the serene setting with a morning round, taking advantage of the driving range to warm up.
Woodstock Golf Course
This historic 9-hole course from 1896 offers classic golfing among New England's natural beauty. Enjoy the serene tree-lined fairways and challenging greens while taking in views of nearby Roseland Lake.
Little River Plaza Shopping Center
This local shopping center serves the community with everyday retail options. Stop by for convenient shopping while exploring the Little River area.
Rocky Hill Refuge
You can take time to visit Rocky Hill Refuge during your travels to Woodstock. Take in the festivals while you're in the area.
Black Pond
Commune with nature and explore the great outdoors at Black Pond during your travels in Woodstock. Take in the festivals while you're in the area.
Woodstock Town Beach
Why not spend a lazy afternoon at Woodstock Town Beach during your trip to Woodstock? Take in the festivals while you're in the area.
Woodstock Hotel Deals
Waterfront Tiny House Cabin Off Grid Camp in Historic Woodstock CT
Woodstock CT
10/10 Exceptional! (2 reviews)
"This is a gem! Can’t wait to go back."
Reviewed on Aug 8, 2026
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock CT
$714 nightly
$808 total
Sep 1 - Sep 2
Total with taxes and fees
9.8/10 Exceptional! (88 reviews)
"In our time at the lake house we were favored by perfect weather. The house is quiet, commodious, well laid out, and completely comfortable for our party of seven people. We live in the same town ourselves, so the other five family members were based in our home, shuttling frequently to the lake. ..."
Reviewed on Aug 21, 2026
Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock CT
$657 nightly
$743 total
Aug 30 - Aug 31
Total with taxes and fees
10/10 Exceptional! (27 reviews)
"We had an amazing stay at this lakeside retreat! Several family members were in town for a wedding. It was the perfect place to unwind. The property was spotless and exactly as described, with a well-equipped kitchen and plenty of space throughout the house. Heather, our host, was friendly, helpful, ..."
Reviewed on Jul 27, 2026
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 |
Closest Airport | Worcester Regional Airport (ORH) |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Taylor Brooke Winery, Harrisville Golf Course and Woodstock Golf Course |
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Frequently asked questions
How much does a Woodstock vacation package cost?
Offering excellent value package deals from $983 on Expedia, you'll be surprised at how little a vacation to Woodstock costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Woodstock?
October, November and December are the best times to search for cheap Woodstock vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on accommodations and flights.
How many days is enough for Woodstock?
With a well-planned itinerary, you can easily tick off the main Woodstock sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Woodstock vacation for longer.
Is it worth booking a vacation package to Woodstock?
From top attractions such as Woodstock Golf Course and Roseland Park Golf Course to its terrific camping, a Woodstock vacation delivers big on experiences. With so much to do and see, find out for yourself why Woodstock is such a good vacation destination.
How to find the best Woodstock package deals?
Finding a cheap Woodstock package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most affordable Woodstock package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Woodstock vacation as a package?
You can enjoy significant savings on your next Woodstock getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Woodstock?
If you've got your Woodstock vacation dates finalized, book as early as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Woodstock vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
