Book Exclusive Woodstock Vacation Packages

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Woodstock flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Wayfinder Newport

Wayfinder Newport

4 out of 5
Price was CA $1,753, price is now CA $1,257 per person
CA $1,257
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Providence (PVD)
Stay at this hotel in Newport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Newport Mansions and Bowen's Wharf are located nearby.
Gilded

Gilded

3 out of 5
Top of the Hill
Price was CA $1,768, price is now CA $1,348 per person
CA $1,348
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Providence (PVD)
Stay at this hotel in Newport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Newport Mansions and Bowen's Wharf are located nearby.
Pleasant View Inn

Pleasant View Inn

3 out of 5
Price was CA $2,220, price is now CA $1,754 per person
CA $1,754
per person
Aug 8 - Aug 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providence (PVD)
Book a stay at this beach hotel in Westerly. Enjoy free parking, a beach locale, and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Misquamicut State Beach and Atlantic Beach Park are located nearby.
The Atlantic Inn

The Atlantic Inn

3.5 out of 5
Price was CA $3,113, price is now CA $2,463 per person
CA $2,463
per person
Aug 8 - Aug 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Providence (PVD)
Stay at this hotel in Block Island. Enjoy daily housekeeping, concierge services, and memory foam beds. Our guests praise the helpful staff in our reviews. Popular attractions Abrams Animal Farm and Nichols Park are located nearby.
The Carriage House Inn Newport

The Carriage House Inn Newport

2.5 out of 5
Price was CA $1,591, price is now CA $1,263 per person
CA $1,263
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Providence (PVD)
Stay at this hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Newport Mansions and Easton's Beach are located nearby.

Top Woodstock hotels deals

Enjoy fishing and kayaking from waterfront cabin retreat in charming Woodstock

Enjoy fishing and kayaking from waterfront cabin retreat in charming Woodstock

Woodstock CT
Get rates
Stay at this cabin in Woodstock. Enjoy patios and sun loungers. Popular attractions Black Pond and West Woodstock Library are located nearby.
Outdoor space
Parking available
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock CT
The price is CA $639 per night
CA $639
CA $1,050 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this beach vacation home in Woodstock. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Roseland Cottage and Taylor Brooke Winery are located nearby.
Kitchen
Washer
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
The price is CA $710 per night
CA $710
CA $1,144 total
Jul 19 - Jul 20
includes taxes & fees
Stay at this vacation home in Woodstock. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Black Pond and West Woodstock Library are located nearby.
Kitchen
Washer
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
Free cancellation
Reserve now, pay when you stay
The price is CA $113 per night
CA $113
CA $126 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this spa resort in Sturbridge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Town Common and Sturbridge Common Historic District are located nearby.
Pool
Spa
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Free cancellation
Reserve now, pay when you stay
The price is CA $137 per night
CA $137
CA $153 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this business-friendly hotel in Southbridge. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Central Mills Historic District and Southbridge Town Common are located nearby.
Pool
Hot tub
La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

3 out of 5
446 Southbridge St Auburn MA
Free cancellation
Reserve now, pay when you stay
The price is CA $105 per night
CA $105
CA $117 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Auburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions DCU Center and Auburn Mall are located nearby.
Breakfast included
Pet-friendly
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See all available properties in Woodstock
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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

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.
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Woodstock Vacations

We get it, geography isn't everyone's strong suit. If you're unsure where Woodstock is situated, it's wise to look into its location before you set foot out the door!

To help get you oriented, Woodstock is located 55 miles (89 kilometers) to the southwest of the noteworthy city of Boston.

Places to visit in Woodstock

A wise man once said 'life is too short to drink bad wine.' Try a drop at Taylor Brooke Winery and discover for yourself if you agree. Need some more options? It doesn't matter whether you're trying to hit a hole-in-one or simply in the mood to brush up on your technique, you'll have a blast at Woodstock Golf Course. And there's more. If you want to bump a few strokes off your score, then head over to Roseland Park Golf Course. Grab your clubs, finesse your swing and unwind with the locals at the 19th hole.

Where do you fly into for Woodstock?

Say hello to awesome adventures in Woodstock. Once you've walked out of Bradley International Airport (BDL), the middle of town will be just 35 miles (56 kilometers) to the east.

Frequently asked questions

How much are vacation packages to Woodstock?
Your vacation daydreams can become a reality in Woodstock for as low as CA $1,257. Packages include flights and hotels, so booking your trip will be easy as pie. The only thing you'll need to focus on is having an incredible time.
Where can I get the best vacation package deals for Woodstock?
With at least 400 airline partners and 1,000,000 hotels around the world, it's hard to go past Travelocity. Take advantage of our comprehensive range and create the perfect Woodstock package deal. Isn't it great when traveling is that easy?
Why should I book my Woodstock vacation bundle with Travelocity?
Travel is all about making cherished memories and leaving all your worries behind — which is why we provide you with a team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our superb range of vacation destinations. So what are you waiting for? There's no time like the present to lock in that vacation you've always wanted.
Can I save money on my Woodstock car rental if I book it with my hotel or flight?
With a Woodstock vacation package, you can bundle your hotel, flight and car bookings and save tons. If you'd love to explore the best of this fantastic area, why not check out Fenway Park? This well-known sight is 88 kilometers from Woodstock. With a rental car, you'll be there in no time.
Which airport is best for Woodstock?
Logan Intl. Airport (BOS), located around 88 kilometers northeast of inner Woodstock, is likely to be where you'll arrive. Your other options are Bradley Intl. Airport (BDL) (56 kilometers away from central Woodstock) and T.F. Green Airport (PVD) (48 kilometers away from central Woodstock).
What is there to do in Woodstock?
Woodstock is brimming with sights to explore, including Roseland Park Golf Course and Harrisville Golf Course. These renowned attractions are on most travelers' to-do lists.
Where should I stay when visiting Woodstock?
Many people opt to hit the hay at the Breathtaking Lakefront Property! Cozy house! Special off-season rates!. It's a great base for your Woodstock escape.

Photos of local treasures

Browse Woodstock vacation photos for more inspiration

A variety of potted flowers and pumpkins on a wooden table in an outdoor setting.
A misty landscape with a body of water, trees, and a bird flying.