South Woodstock Vacations from $360

Book a Hotel + Flight or Car together to unlock savings

Your South Woodstock Vacation

With all the details planned before you head off, our South Woodstock vacation packages mean you can concentrate on enjoying your getaway. Whether you base yourself in the neighborhood of Killingly, which is great for nature, or someplace else, this interesting city offers plenty of discoveries. If your trip to South Woodstock includes some sightseeing, drop by much-loved attractions like Taylor Brooke Winery, Harrisville Golf Course and Woodstock Golf Course. A couple of clicks is all it takes to create a tailored South Woodstock vacation on Expedia.

The Latest South Woodstock Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Cromwell/Middletown

Super 8 by Wyndham Cromwell/Middletown

2 out of 5
per person
Aug 22 - Aug 27
found 16 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Hartford (BDL)
7/10 Good! (999 reviews)
Price is cheap. Location is good and easy to come and go. Room, AC conditions and internet speed greatly depend on what room you get. Furniture and beddings are quite aged and need replacement.

Reviewed on Jun 1, 2024

Residence Inn by Marriott Hartford Downtown

Residence Inn by Marriott Hartford Downtown

3.5 out of 5
Downtown Hartford
Save 100% on your flight
per person
Aug 22 - Aug 27
found 16 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Hartford (BDL)
8.8/10 Excellent! (389 reviews)
A bit run down hotel but nice staff and good area

Reviewed on May 23, 2024

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

2.5 out of 5
per person
Aug 22 - Aug 27
found 16 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Hartford (BDL)
8/10 Very Good! (1,500 reviews)
Front desk agent needs to be better trained to acknowledge a guest who is standing in front of them.

Reviewed on Jun 4, 2024

Baymont by Wyndham East Windsor Bradley Airport

Baymont by Wyndham East Windsor Bradley Airport

2.5 out of 5
per person
Aug 22 - Aug 27
found 16 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Hartford (BDL)
6/10 (1,001 reviews)
It smelled of smoke everywhere.

Reviewed on May 20, 2024

Manchester Inn and Suites

Manchester Inn and Suites

2.5 out of 5
per person
Aug 22 - Aug 27
found 16 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Hartford (BDL)
6.6/10 (1,002 reviews)
It was an average stay

Reviewed on May 28, 2024

South Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
1,300
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Taylor Brooke Winery, Harrisville Golf Course and Woodstock Golf Course

South Woodstock Hotel Deals

Breathtaking Lakefront Property! Cozy house! Special off-season rates!
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
Woodstock
10/10 Exceptional! (5 reviews)
Best weekend getaway
"What a wonderful weekend our book club had staying in the beautiful lake front house! So relaxing, and quiet! Great little town with charming little places to enjoy. Our visit to the local winery was so much fun and the gals there told us to check out a local town celebration which we enjoyed going ..."

Reviewed on Apr 21, 2024

Get rates
Breathtaking Lakefront Property! Cozy house! Special off-season rates!
Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is $107 per night from Jun 13 to Jun 14
$107
$120 total
includes taxes & fees
Jun 13 - Jun 14
9/10 Wonderful! (1,013 reviews)
"Excellent staff. Kid friendly."

Reviewed on Jun 2, 2024

Wellsworth Hotel
Inn on Storrs (formerly Best Western Storrs)
Inn on Storrs (formerly Best Western Storrs)
3.5 out of 5
123 Storrs Road, Willimantic, CT
Fully refundableReserve now, pay when you stay
The price is $144 per night from Jun 7 to Jun 8
$144
$165 total
includes taxes & fees
Jun 7 - Jun 8
7.8/10 Good! (1,001 reviews)
"Good place to stay to sleep, but this is the second year in a row we stayed here and the pool and hot tub chemicals were way off both times. Maybe some one needs training on correct pool chemicals, but just being in the water, with out going under water, your eyes would burn. Again, not a big deal ..."

Reviewed on Jun 3, 2024

Inn on Storrs (formerly Best Western Storrs)
See all 153 properties in South 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a South Woodstock vacation package cost?
Less than you might think — from as low as $360, actually! By combining hotels, flights and car rentals into your own custom-built vacation package, your South Woodstock escape is only clicks away.
How do I get a cheap travel package to South Woodstock?
Secure flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with a South Woodstock vacation package. It’s as simple as that! From flights and hotels to activities and rental cars, Expedia makes traveling cheaply a cinch. And with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you won’t be short of choice.
Where should I stay in South Woodstock?
With loads to explore in South Woodstock, it makes sense to lock in a hotel close to its attractions. Taylor Brooke Winery, Roseland Park Golf Course and Woodstock Golf Course are some top ones to put on your must-see list.
How far in advance should I book my South Woodstock vacation?
While prices fluctuate, we generally advise booking your spot as early as possible. Many international airfares can be found on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still get lucky. Cheap journeys to South Woodstock sometimes occur just weeks before departure.
What does an Expedia South Woodstock travel package include?
Expedia has all you need to arrange your South Woodstock getaway, but what goes into your package is up to you. Pick from a combination of rental cars, hotels and flights. Chasing some activities or tours to keep you entertained? Once you’ve made your booking, you can add them too. Whatever your budget or style, there’s a package to match your needs.
What should I know before booking a South Woodstock travel package?
Whether it’s relaxation or adventure you’re chasing, a South Woodstock vacation package lets you organize your escape your way. Plus, you’ll get access to great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a South Woodstock Expedia vacation package?
Yes — that’s the beauty of an Expedia package. You’re the boss! We have access to more than 550 partner airlines throughout the world, so you have options galore when planning your South Woodstock adventure.
If I'm not able to travel, can I cancel my South Woodstock vacation package?
Plans can change in a flash, so yes, you can. You may be able to amend or cancel your South Woodstock vacation package at no cost within 24 hours of booking. For older bookings, you can still cancel or make changes, but your airline, hotel or car rental company may charge additional fees. Looking for more information? Take a look at our Customer Service Portal. We’ll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in South Woodstock

Image for Taylor Brooke Winery

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
Image for Roseland Cottage

Roseland Cottage

You can learn about the history of Woodstock with a stop at Roseland Cottage. Check out the top-notch restaurants or lively bars in this family-friendly area.

Roseland Cottage
Image for Woodstock 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

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.