Woodstock Vacations from $534

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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.
Hotel Providence

Hotel Providence

4 out of 5
Downtown Providence
Save 100% on your flight
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Providence (PVD)
8.6/10 Excellent! (1,000 reviews)
Wonderful boutique hotel. Many originals antique furnishings and paintings throughout hotel. Room was nice size with modern bathrooms and deco style room furnishings. Decent fitness room in basement enough for full workout. Nice breakfast bar included and coffee/tea setup in lobby throughout day. There are homeless in area and throughout city but was never bothered. Very walkable location to stores and eateries. Lovely staff. Will return.

Reviewed on Jul 22, 2025

Wayfinder Newport

Wayfinder Newport

4 out of 5
Save 100% on your flight
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Providence (PVD)
7.8/10 Good! (849 reviews)
The rooms were very clean and updated. Very nice stay overall. Reasonably priced.

Reviewed on Jul 22, 2025

The Cottage At Amos Lake

The Cottage At Amos Lake

3.5 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Providence (PVD)
9.8/10 Exceptional! (61 reviews)
We were greeted by host as soon as well drove in. The place was clean, smelled clean. I wish we had more time to explore the grounds. Very close to Foxwoods. The bed was great, comfy. Definitely will be back.

Reviewed on Jun 8, 2025

Club Wyndham Inn on the Harbor

Club Wyndham Inn on the Harbor

2.5 out of 5
Downtown Newport
Save 100% on your flight
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Providence (PVD)
8.4/10 Very Good! (396 reviews)
Loved the room, the amenities, location, and especially the harbor view. I regret that I didn't call ahead to make sure the sofa-bed was made up. Biggest problem was trying to find where to check in!! Seriously, this was not easy. No signage anywhere, and the check-in area was so insignificant, again with no signage, that I didn't know I'd found it. There was nobody there!

Reviewed on Jun 16, 2025

Club Wyndham Inn on Long Wharf

Club Wyndham Inn on Long Wharf

2.5 out of 5
Downtown Newport
Save 100% on your flight
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Providence (PVD)
8.8/10 Excellent! (278 reviews)
The room was a bit too worn. The windows— the only ones- didn’t open very wide and one window didn’t open at all. Also the vanity mirror in the bathroom was broken. But the view was lovely.

Reviewed on May 14, 2025

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Discover the most popular places to visit in Woodstock

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 Golf Course

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

Woodstock Golf Course

Little River Plaza Shopping Center

You can browse for the perfect souvenirs at Little River Plaza Shopping Center during your visit to South Woodstock. While in this quaint area, you can savor the top-notch restaurants.

Little River Plaza Shopping Center

Woodstock Hotel Deals

Secluded 2-Acre Lakefront Home! Book Your Retreat!

Secluded 2-Acre Lakefront Home! Book Your Retreat!

Woodstock
9.8/10 Exceptional! (66 reviews)
Just what we needed
"The property is very nice and roomy. If you have a big family like ours and you need a place in this part of CT, you’re in luck."

Reviewed on Jun 21, 2025

Get rates
Secluded 2-Acre Lakefront Home! Book Your Retreat!
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Jul 24 to Jul 25
$111 total
Jul 24 - Jul 25
Total includes taxes and fees
8.8/10 Excellent! (1,464 reviews)
"They have made major upgrades to their property while retaining its wonderful historic character. Room was modern and spacious yet still charming."

Reviewed on Jul 21, 2025

Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Jul 24 to Jul 25
$133 total
Jul 24 - Jul 25
Total includes taxes and fees
9/10 Wonderful! (1,248 reviews)
"Parking, ice machines vending and water are a walk from most room. Pool area is nice, hotel grounds well kept!"

Reviewed on Jul 21, 2025

Wellsworth Hotel
See all 279 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 $534 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.