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.

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Stockbridge Hotel Deals

Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
The price is CA $177 per night from Jul 10 to Jul 11
CA $177
CA $195 total
Jul 10 - Jul 11
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."

Reviewed on Jun. 26, 2025

Comfort Inn Rutland - Killington
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 $151 per night from Jul 13 to Jul 14
CA $151
CA $166 total
Jul 13 - Jul 14
includes taxes & fees
7/10 Good! (1,001 reviews)
"Convenient booked last minute and it had large rooms with a kitchen"

Reviewed on Jul. 1, 2025

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 $624 per night from Jul 13 to Jul 14
CA $624
CA $747 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (521 reviews)
"Relaxing"

Reviewed on Jun. 25, 2025

Woodstock Inn & Resort
See all 2,087 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

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 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.