Stockbridge Vacation Packages

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Your Stockbridge Vacation

Art, food, entertainment and more … It's all waiting for you with a Stockbridge vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's hard to forget. Any trip to Stockbridge has to include a little sightseeing. White River Golf Club is a popular place to begin exploring. Your perfect Stockbridge vacation is clicks away. Search hotels, flights and more on Expedia for an adventure that's tailored just for you.

Top Stockbridge Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was CA $1,381, price is now CA $1,221 per person
CA $1,221
per person
Oct 1 - Oct 5
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (499 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on Aug. 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $3,248, price is now CA $2,507 per person
CA $2,507
per person
Oct 1 - Oct 5
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (806 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug. 18, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was CA $2,911, price is now CA $2,356 per person
CA $2,356
per person
Oct 1 - Oct 5
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.6/10 Exceptional! (57 reviews)
Very authentic and comfortable.

Reviewed on Aug. 22, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was CA $1,860, price is now CA $1,549 per person
CA $1,549
per person
Oct 1 - Oct 5
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Lebanon (LEB)
9/10 Wonderful! (732 reviews)
Great place to stay and see the beautiful mt ascutney

Reviewed on Aug. 24, 2025

Chalet 239

Chalet 239

2 out of 5
Price was CA $1,600, price is now CA $1,384 per person
CA $1,384
per person
Oct 1 - Oct 5
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Springfield (VSF)
9.4/10 Exceptional! (74 reviews)
Teh staff were friendly and helpful. Immediately upon booking I received a text message from the staff letting me know someone was there to help with any questions. checking in was easy and the hotel was very clean. The room, beds and bathroom were all clean and well kept. The free breakfast was a plus.

Reviewed on Aug. 12, 2025

Ready to book your vacation to Stockbridge?

 

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Stockbridge Hotel Deals

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Sep 7 to Sep 8
CA $148
CA $163 total
Sep 7 - Sep 8
includes taxes & fees
White River Inn and Suites
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $550 per night from Sep 2 to Sep 3
CA $550
CA $666 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul. 30, 2025

Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Sep 4 to Sep 5
CA $181
CA $210 total
Sep 4 - Sep 5
includes taxes & fees
9/10 Wonderful! (874 reviews)
We’ll be back.
"Beautiful area, outside of facility looks dated, but that’s not realistic to change. Inside has had a nice update. The staff is very friendly and helpful. We had an inconsiderate and noisy person upstairs over us, just a matter of who is there. We would surely stay here again."

Reviewed on Aug. 23, 2025

The Mountain Inn at Killington
See all 2,073 properties in Stockbridge
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
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Frequently asked questions

How much does a Stockbridge vacation package cost?
You can grab a vacation package to this destination from CA $1,221 on Expedia. But how much your vacation to Stockbridge costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Stockbridge?
To pick up cheap Stockbridge vacation packages, organize your getaway outside of peak times such as school holidays. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Stockbridge?
The ideal duration of your Stockbridge vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to tick off all the major sights and explore some hidden gems along the way.
How to find the best Stockbridge package deals?
Begin your search for a Stockbridge package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Stockbridge package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Stockbridge getaway off to a flying start.
Is it cheaper to book a Stockbridge vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Stockbridge escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Stockbridge?
Score fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Stockbridge adventure.
How to plan a trip to Stockbridge?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Stockbridge.
  2. Set a budget: Consider costs like transportation, flights and meals when calculating how much to put aside for your trip to Stockbridge. Then, pick a property that fits your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Decide how many days away: Start by compiling a list of the attractions and activities you'd like to experience in Stockbridge. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Stockbridge vacation package.

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