Woodstock Vacations from $554

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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.
The Cottage Inn At Amos Lake

The Cottage Inn At Amos Lake

3 out of 5
Price was $756, price is now $554 per person
$554
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Providence (PVD)
9.8/10 Exceptional! (98 reviews)
My wife and I were very pleased with our stay. The whole place was super clean. There was a fridge full of water, o.j., creamer, bagel variety and other items to snack on such as bananas, cereal, oatmeal, coffee, tea, etc. We met one of the hosts who was wonderful. Various activities and places to eat listed on a white board. Very organized and helpful. Would highly recommend and will be coming back.

Reviewed on Apr 28, 2026

The Preserve Sporting Club & Resort

The Preserve Sporting Club & Resort

4 out of 5
Save 100% on your flight
Price was $2,279, price is now $1,497 per person
$1,497
per person
Jun 21 - Jun 24
found 2 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
8.8/10 Excellent! (9 reviews)
The resort itself stood out so beautiful!

Reviewed on Jan 6, 2026

Dye House

Dye House

2 out of 5
Olneyville
Save 100% on your flight
Price was $2,000, price is now $1,382 per person
$1,382
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Providence (PVD)
8.6/10 Excellent! (21 reviews)
Highly recommend the Loft as it was a beautiful space. The Heddle room has a glass window in the door to the bathroom. Technically you could shower in privacy but I would rather a solid door. Staff handled an issue with our original room well. They were immediately available when I called and provided both a short term (moving rooms for the night) and long term solution (fixing the issue) plan within ten minutes. Heddle room is a good option if you need a place to sleep and will be otherwise out for the day. Loved the digital building and door keys. Easy parking. The entire building space is quite unique and stylish.

Reviewed on Nov 9, 2025

Langworthy Inn

Langworthy Inn

3.5 out of 5
Save 100% on your flight
Price was $885, price is now $640 per person
$640
per person
Jul 2 - Jul 5
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Providence (PVD)
9.8/10 Exceptional! (18 reviews)
Friendly and peaceful setting

Reviewed on Nov 22, 2025

The Underwood-Hale House

The Underwood-Hale House

4 out of 5
College Hill
Price was $1,563, price is now $1,153 per person
$1,153
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Providence (PVD)
9.8/10 Exceptional! (81 reviews)
Comfortable bed and spacious!

Reviewed on Apr 24, 2026

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Discover the most popular places to visit in Woodstock

Roseland Park Golf Course

Enjoy a round of golf in Woodstock at Roseland Park Golf Course. Check out the lively bars or top-notch restaurants in this family-friendly area.

Roseland Park Golf Course

Woodstock Golf Course

Enjoy a round of golf in Woodstock at Woodstock Golf Course. Check out the lively bars or top-notch restaurants in this quaint area.

Woodstock Golf Course

Taylor Brooke Winery

You can enjoy a tasting or tour at Taylor Brooke Winery during your travels to Woodstock. While in this family-friendly area, you can savor the top-notch restaurants.

Taylor Brooke Winery

Woodstock Hotel Deals

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
$682 nightly
The price is $772 total per night from May 17 to May 18
$772 total
May 17 - May 18
Total with taxes and fees
9.8/10 Exceptional! (84 reviews)
We stayed here for my nieces wedding. The house was very well appointed in a beautiful setting. The kitchen is huge! We spent most of our time in the house gathered around the table laughing and eating. We had cold raining weather so we did not get to enjoy the grounds as much as I would have liked ...

Reviewed on Apr 20, 2026

Secluded 2-Acre Lakefront Home! Book Your Getaway!
The McClellan Mansion

The McClellan Mansion

Woodstock CT
10/10 Exceptional! (2 reviews)
Beautiful historic home with all the modern conveniences. Great set-up with every room having its own bathroom, and plenty of comfortable commons spaces too.

Reviewed on Feb 8, 2026

Get rates
The McClellan Mansion
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $120 total per night from May 25 to May 26
$120 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (1,508 reviews)
Was great!

Reviewed on May 13, 2026

Wellsworth Hotel
See all 316 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
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 $554 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.