Stockbridge Vacations from $616

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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.

The Latest Stockbridge vacation packages

Price found within the past 48 hours. Click for updated prices.
Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
Sep 25 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
10/10 Exceptional! (5 reviews)
Great location , friendly and knowledgeable staff !

Reviewed on Jun 14, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (762 reviews)
Great location!! Very accommodating and clean.

Reviewed on Jun 28, 2025

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Rutland (RUT)
9.4/10 Exceptional! (31 reviews)
We stayed here for the weekend for a wedding and it was so comfortable, clean, and quiet since you get your own cabin. We loved it and would definitely come back! The property was also really accommodating to requests and needs in a timely manner

Reviewed on May 16, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
per person
Sep 25 - Sep 28
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Lebanon (LEB)
9/10 Wonderful! (712 reviews)
Excellent property large spacious rooms great restaurant on property

Reviewed on Jun 28, 2025

Chalet 239

Chalet 239

2 out of 5
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
9.4/10 Exceptional! (66 reviews)
Perfect Chaet!!! Will definitely come back and highly recommend.

Reviewed on Apr 13, 2025

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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
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $144 total per night from Jul 10 to Jul 11
$144 total
Jul 10 - Jul 11
Total includes taxes and fees
8/10 Very Good! (1,000 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
$111 nightly
The price is $122 total per night from Jul 13 to Jul 14
$122 total
Jul 13 - Jul 14
Total includes taxes and 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
$499 nightly
The price is $549 total per night from Jul 13 to Jul 14
$549 total
Jul 13 - Jul 14
Total includes taxes and 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.

Find the Best Stockbridge Vacation Packages

Stockbridge Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Lakota Lake, White River Golf Club and Little Pico Mountain

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Frequently asked questions

How much does a Stockbridge vacation package cost?
Offering great value package deals from $616 on Expedia, you'll be thrilled with how little a vacation to Stockbridge costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Stockbridge?
You can typically find reduced prices and greater availability in March, May and October. Explore our cheap Stockbridge vacation packages and you could get some great off-season deals.
How many days is enough for Stockbridge?
Generally, a handful of days is enough to visit the top attractions during your Stockbridge vacation. However, if you want to have some time to rest or go on day trips, consider extending your trip.
How to find the best Stockbridge package deals?
Landing a cheap Stockbridge package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Stockbridge package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Stockbridge vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Stockbridge vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Stockbridge?
Secure incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Stockbridge escape.
Does Expedia offer Book Now, Pay Later Stockbridge vacation packages?
Your Stockbridge trip should be a relaxing escape from your busy life, not a source of money-related stress. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.