Woodstock Vacations from $469
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Aqua Blue Hotel
Narragansett Pier
$469
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Providence (PVD)
7/10 Good! (1,005 reviews)
Great location! Restaurants very close by! Beautiful area! Room with very small balcony but a beautiful view of the ocean! The room was clean, no problem with the A/C, front desk gentleman was helpful as we had a minor issue but it was taken care of without too much trouble! Overall it was a good experience!
Reviewed on Oct 8, 2026
Marina Bay Cottages
$1,096
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Providence (PVD)
9.6/10 Exceptional! (130 reviews)
Great place to stay with kids! The game room was so helpful with a rainy day. Perfect size, clean, well equipped. Will definitely be back next summer!
Reviewed on Oct 7, 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.
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.
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.
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.
Goodell Morse Memorial Forest
You can take time to visit Goodell Morse Memorial Forest during your travels to Woodstock. Take in the festivals while you're in the area.
Joyce Townsend Collins Memorial Woodland
This 27-acre forest sanctuary offers a serene habitat for wildlife within a crucial migration corridor. Wander among hemlocks and mountain laurel while watching for deer and birds in this peaceful woodland retreat.
West Woodstock Library
West Woodstock Library is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Take in the festivals while you're in the area.
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 Hotel Deals
Waterfront Tiny House Cabin Off Grid Camp in Historic Woodstock CT
Woodstock CT
9.2/10 Wonderful! (5 reviews)
"Amazing place to stay. Peaceful scenery, beautiful cabin, kind hosts! Great place to unplug and relax. Hosts were great at communicating and explaining how everything worked."
Reviewed on Sep 16, 2026
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock CT
$562 nightly
$637 total
Nov 1 - Nov 2
Total with taxes and fees
9.8/10 Exceptional! (93 reviews)
"Cozy, clean and lovely! The lake is beautiful and serene. We had an enjoyable stay, wish we could have stayed longer. There was excellent communication with the host before and during our stay, especially with the incoming storm. I would return and stay again!"
Reviewed on Sep 27, 2026
Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock CT
10/10 Exceptional! (28 reviews)
"We were in the area for a wedding at Willow Hill. This could not have been a better home base for the weekend. It was close to the venue, and the beautiful lakeside setting made it the perfect retreat when we weren’t tied up with wedding duties. The layout worked well for our party of six, and we ..."
Reviewed on Sep 11, 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 |
More vacations you might like
Frequently asked questions
How much does a Woodstock vacation package cost?
Offering excellent value package deals from $469 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.
Explore a world of travel with Expedia
- Hotels with Bars in Putnam
- Hostels in Woodstock
- Hotels near Mohegan Sun Casino
- B&B in Putnam
- Pet-Friendly Hotels in Putnam
- 3 Star Hotels in Woodstock
- Pomfret Hotels
- 5 Star Hotels in Putnam
- Hartford Hotels
- Cabin Rentals in Woodstock
- Motels in Pomfret
- Hotels near University of Connecticut
- Motels in Woodstock
- Villas in Woodstock
- Hotels with a Pool in Woodstock
- Hilton Hotels in Pomfret
- Thompson Hotels
- Motels in Putnam
- Motels in South Woodstock
- 2 Star Hotels in Pomfret
- 4 Star Hotels in Pomfret
- 5 Star Hotels in Woodstock
- Putnam Hotels
- Woodstock Hotels
- Dayville Hotels
- Hotels near Taylor Brooke Winery
- B&B in Pomfret
- Hotels near Woodstock Golf Course
- South Woodstock Hotels
- Cottages in Pomfret
- Brooklyn Hotels
- Hotels near Bradley Intl.
- Hotels near Foxwoods Resort Casino
- Resorts in Woodstock
- Mystic Hotels
- Vacation Homes in Pomfret
- Flights from Bradley Intl.
- Flights to Putnam
- Flights from Charlotte (CLT) to Hartford (BDL)
- Flights from Las Vegas (LAS) to Hartford (BDL)
- Flights from Orlando (MCO) to Hartford (BDL)
- Flights from Denver (DEN) to Hartford (BDL)
- Flights to Hartford
- Flights from Woodstock
- Flights from Tampa (TPA) to Hartford (BDL)
- Flights from Los Angeles (LAX) to Hartford (BDL)
- Flights to Pomfret
- Flights from Dallas (DFW) to Hartford (BDL)
- Flights to Bradley Intl.
- Flights from Detroit (DTW) to Hartford (BDL)
- Flights from Atlanta (ATL) to Hartford (BDL)
- Flights from Fort Lauderdale (FLL) to Hartford (BDL)
- Flights from Fort Myers (RSW) to Hartford (BDL)
- Flights from Raleigh (RDU) to Hartford (BDL)
- Flights from Chicago (ORD) to Hartford (BDL)
- Flights from Washington (DCA) to Hartford (BDL)
- Flights from Putnam
- Flights to Woodstock
- University of Connecticut
- Canterbury Vacations
- Storrs Vacations
- Prudence Crandall Museum
- Griswold Vacations
- Little River Plaza Shopping Center
- Coventry Vacations
- Visit Woodstock
- Lebanon Vacations
- Tolland Vacations
- Senator Thomas J Dodd Memorial Stadium
- Nathan Hale Homestead
- Baltic Vacations
- Putnam Vacations
- Brooklyn Vacations
- J. M. Sarnik & Sons' The Old General Store
- Stafford Springs Vacations
- Moosup Pond Beach
- Visit Pomfret
- Moosup Vacations
- Willington Vacations
- Bolton Vacations
- Chaplin Museum
- Thompson Vacations
- Hopeville Pond State Park
- Visit Putnam
- Foxwoods Resort Casino
- Jorgensen Center for the Performing Arts
- Olde Mistick Village
- Mohegan Sun Golf Club
- Ocean Beach Park
- Davis Park
- Harry A. Gampel Pavilion
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
