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.
Gilded

Gilded

3 out of 5
Top of the Hill
Save 100% on your flight
Price was $620, price is now $464 per person
$464
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Providence (PVD)
This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free self-serve breakfast each morning. A garden is also provided.
Wayfinder Newport

Wayfinder Newport

4 out of 5
Save 100% on your flight
Price was $941, price is now $605 per person
$605
per person
Dec 22 - Dec 29
found 17 hours ago
Roundtrip flight included
Orlando (MCO) 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 free WiFi. A coffee shop, a lobby fireplace, and express check-out are also on offer.
Holiday Inn Express Mystic by IHG

Holiday Inn Express Mystic by IHG

2.5 out of 5
Price was $644, price is now $470 per person
$470
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Providence (PVD)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
The Underwood-Hale House

The Underwood-Hale House

2 out of 5
College Hill
Price was $965, price is now $705 per person
$705
per person
Dec 26 - Dec 29
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Providence (PVD)
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. 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. A terrace and a garden are also provided.
Sandy Shore Motel

Sandy Shore Motel

2.5 out of 5
Price was $667, price is now $495 per person
$495
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Providence (PVD)
This traditional motel features a private beach and 2 restaurants. Dine at the beachfront restaurant and relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Top Woodstock hotels deals

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

$448 nightly
The price is $508 total per night
$508 total
Nov 1 - Nov 2
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!

$448 nightly
The price is $508 total per night
$508 total
Nov 1 - Nov 2
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
$84 nightly
The price is $94 total per night
$94 total
Oct 27 - Oct 28
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
$116 nightly
The price is $130 total per night
$130 total
Oct 19 - Oct 20
Total with taxes and fees
This smoke-free 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
Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

2.5 out of 5
426 Southbridge St, Auburn, MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-in. There's a gym on site, and a fireplace in the lobby and express check-out are also provided.
Breakfast included
Parking included
Inn on Storrs

Inn on Storrs

3.5 out of 5
123 Storrs Road, Willimantic, CT
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $180 total per night
$180 total
Oct 26 - Oct 27
Total with taxes and fees
This motel features 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
Don't see what you're looking for?
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.

Popular places to visit

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

Frequently asked questions

How much are vacation packages to Woodstock?
Your vacation daydreams can become a reality in Woodstock for as low as $464. 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