Deals on vacations and trips to Woodstock

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Woodstock flight + hotel 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 $1,244, price is now $838 per person
$838
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free self parking and a free area shuttle. A coffee shop, free WiFi in public areas, and a lobby fireplace are also on offer.
The Preserve Sporting Club & Resort

The Preserve Sporting Club & Resort

4 out of 5
Save 100% on your flight
Price was $7,642, price is now $4,597 per person
$4,597
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
This smoke-free hotel features a golf course, a full-service spa, and 2 restaurants. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and free grocery shopping service.
Dye House

Dye House

2 out of 5
Olneyville
Save 100% on your flight
Price was $1,526, price is now $1,005 per person
$1,005
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
This hotel features a virtual front desk. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Take advantage of the free self parking.
Holiday Inn Express Newport North - Middletown by IHG

Holiday Inn Express Newport North - Middletown by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,400, price is now $944 per person
$944
per person
Oct 23 - Oct 30
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Fox Point Landing Residences

Fox Point Landing Residences

4 out of 5
Fox Point
Save 100% on your flight
Price was $1,409, price is now $969 per person
$969
per person
Oct 9 - Oct 12
found 12 hours ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
This apartment features laundry facilities. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Take advantage of the free self parking.

Top Woodstock hotels deals

Waterfront Tiny House Cabin Off Grid Camp in Historic Woodstock CT

Waterfront Tiny House Cabin Off Grid Camp in Historic Woodstock CT

Woodstock CT
Get rates
This cabin features barbecue grills.
Outdoor Space
Parking available
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock CT
$686 nightly
The price is $776 total per night
$776 total
Aug 3 - Aug 4
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock CT
$657 nightly
The price is $743 total per night
$743 total
Aug 3 - Aug 4
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
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
$88 nightly
The price is $98 total per night
$98 total
Aug 12 - Aug 13
Total with taxes and fees
A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this Colonial resort. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Pool
Spa
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $136 total per night
$136 total
Aug 10 - Aug 11
Total with taxes and fees
This traditional hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
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
$90 nightly
The price is $101 total per night
$101 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's express check-out and multilingual staff can provide around-the-clock assistance.
Breakfast included
Pet friendly
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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

Roseland Cottage

You can study the exhibits at Roseland Cottage, a museum with a storied past, during your travels to Woodstock. Check out the lively bars or top-notch restaurants in this quaint area.
See properties

Frequently asked questions

How much are vacation packages to Woodstock?
Your vacation daydreams can become a reality in Woodstock for as low as $838. 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 55 mi 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 55 mi northeast of inner Woodstock, is likely to be where you'll arrive. Your other options are Bradley Intl. Airport (BDL) (35 mi away from central Woodstock) and T.F. Green Airport (PVD) (30 mi 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.