Woodstock Vacations from $259

Book a Hotel + Flight or Car together to unlock savings

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.
Wayfinder Newport

Wayfinder Newport

4 out of 5
Save 100% on your flight
Price was $418, price is now $259 per person
$259
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Providence (PVD)
8/10 Very Good! (1,009 reviews)
Early Checkin was available. This is clearly an older motel, but rooms are updated and beautiful. Food and bar were available and open late.

Reviewed on Oct 20, 2025

Club Wyndham Newport Onshore

Club Wyndham Newport Onshore

3 out of 5
Downtown Newport
Save 100% on your flight
Price was $580, price is now $399 per person
$399
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Providence (PVD)
8.6/10 Excellent! (178 reviews)
Great location with a beautiful view of marina. Very clean and has kitchen amenities. Will recommend to friends and family.

Reviewed on May 31, 2025

The Vanderbilt, Auberge Collection

The Vanderbilt, Auberge Collection

5 out of 5
Downtown Newport
Save 100% on your flight
Price was $1,246, price is now $877 per person
$877
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Providence (PVD)
9.2/10 Wonderful! (303 reviews)
Beautiful and unique property, lovely and attentive staff. Would love to visit again!

Reviewed on Aug 18, 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
Price was $659, price is now $480 per person
$480
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Providence (PVD)
8.8/10 Excellent! (286 reviews)
First night we parked in garage area to left of door and when we opened back of suv to get luggage, it scraped the top. Wish rooftop was open longer so we could watch the stars.

Reviewed on Oct 21, 2025

Hotel Providence

Hotel Providence

4 out of 5
Downtown Providence
Price was $900, price is now $664 per person
$664
per person
Dec 13 - Dec 15
found 23 hours ago
Roundtrip non-stop flight included
Sacramento (SAC) to Providence (PVD)
8.4/10 Very Good! (1,000 reviews)
The room was ample, well supplied and clean. The hotel is located in a centric area.

Reviewed on Oct 17, 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 quaint area, you can savor the top-notch restaurants.

Taylor Brooke Winery

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 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

Woodstock Hotel Deals

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock
$450 nightly
The price is $510 total per night from Nov 1 to Nov 2
$510 total
Nov 1 - Nov 2
Total with taxes and fees
9.8/10 Exceptional! (74 reviews)
What a wonderful home! This house was huge! There were plenty of rooms for our family, but 3 of my relatives did not make it.The first floor had a bedroom right near the main floor bathroom which was perfect for my 82 year old parents.My husband and I stayed in the upstairs master suite.We were there ...

Reviewed on Oct 8, 2025

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock
$420 nightly
The price is $475 total per night from Nov 1 to Nov 2
$475 total
Nov 1 - Nov 2
Total with taxes and fees
9.8/10 Exceptional! (18 reviews)
We used the kitchen and dining room, as well as the living room. Clean, warm, friendly place with an excellent view. Could not be happier. Thanks!

Reviewed on Oct 14, 2025

Stunning Lakefront Escape! Book Your Dream Getaway!
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 Oct 26 to Oct 27
$111 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,551 reviews)
Would stay again for location.
Room was outdated and had a musty odor. Shower was warm at best. Got hit for a min and then back to warm. Bed and pillows were ehh. Not terrible but definitely not plush comfort.

Reviewed on Oct 19, 2025

Publick House Historic Inn and Country Motor Lodge
See all 288 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 $259 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.