Woodstock Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
Your Woodstock Holiday
Prepare to experience Woodstock on your terms with a custom Woodstock holiday package! Uncovering the best parts of this interesting city is simple with a base in a neighbourhood 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 Centre and Harrisville Golf Course. Don't delay visiting this destination any longer. The perfect Woodstock holiday is only a few clicks away with Expedia.
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Worcester Regional Airport (ORH) |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Taylor Brooke Winery, Roseland Park Golf Course and Woodstock Golf Course |
Top hotels in Woodstock
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 8 Aug 2026
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock CT
£601
1 Sept - 2 Sept
includes taxes & fees
9.8/10 Exceptional! (87 reviews)
"Beautiful lake house. The dock with the kayaks and paddle boat made it so much fun for the kids. The dock isnt far from the house but there a decent hill down to it. Totally manageable for most people though. The open house concept kitchen area made it great for everyone to be together."
Reviewed on 17 Jul 2026
Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock CT
£541
31 Aug - 1 Sept
includes taxes & 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 27 Jul 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.
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." Savour 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 centre 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.
Frequently asked questions
How much does a Woodstock travel package cost?
From as low as . Yes, you read that right. Our Woodstock packages are an easy way to make your budget stretch further. Bundle your flights, hotels and rental car and discover this lively destination.
If I'm not able to travel, can I cancel my Woodstock travel package?
We totally understand — life can throw you the odd curveball. If you've locked in a Woodstock travel package and need to change or cancel it, we can help. We recommend checking out our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to cancel and rebook free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to Woodstock?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got everything you need. Pick and choose the combination that best suits you and watch your savings grow. We know a travel package is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options globally, which lets you customize your Woodstock adventure.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Expedia has teamed up with online lender Klarna to make your next trip easier on your budget. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Check out these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
- Low deposit holidays: When you spot an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock it in.
Where should I stay in Woodstock?
A trip to Woodstock wouldn't be complete without paying a visit to Woodstock Golf Course, Roseland Park Golf Course and Harrisville Golf Course. Stay near these sights and make sightseeing a breeze.
What are the top hotels in Woodstock?
Get your holiday off to a great start by locking in a room at La Quinta Inn & Suites by Wyndham Norwich-Plainfield-Casino. It's one of most popular properties in Woodstock. Another comfortable option is Comfort Inn & Suites.
How far in advance should I book my Woodstock holiday?
It can be difficult to know when is the perfect time to book your trip to Woodstock. But generally the earlier you book, the lower the prices. In some cases, you can lock in your flights and hotels nearly 12 months before your departure date. If you're considering a last-minute getaway, no need to stress! There are fantastic deals advertised on Expedia every single day.
What does an Expedia Woodstock travel package include?
Hotels, flights and rental cars, or any combination of them — it's up to you! Whether you're exploring Woodstock with the family or travelling by yourself, there's a bundle to suit your budget and style. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking a Woodstock travel package?
A package can be more affordable than separately booking all you need for your adventure. For example, bundle your flights, hotels and rental cars and save big. Whatever kind of holiday you're planning, there's bound to be a package that's right for you.
Can I choose my airline with a Woodstock Expedia travel package?
Expedia has access to more than 550 partner airlines globally, so you definitely can. Just select the carrier you want and craft your ideal Woodstock holiday.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
