Stockbridge Vacations from $574

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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.
Chalet 239

Chalet 239

2 out of 5
Price was $682, price is now $574 per person
$574
per person
Jul 6 - Jul 10
found 7 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
9.4/10 Exceptional! (125 reviews)
Staff very helpful. Everything was very clean

Reviewed on May 17, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,283, price is now $980 per person
$980
per person
Jul 24 - Jul 26
found 8 hours ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (926 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants

Reviewed on May 12, 2026

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $768, price is now $610 per person
$610
per person
Jul 6 - Jul 10
found 7 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (1,000 reviews)
Some maintenance issues But plenty of character

Reviewed on May 15, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $926, price is now $740 per person
$740
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.4/10 Exceptional! (926 reviews)
The condo was spacious and well equipped. The continental breakfast was convenient. The views of the lake are breathtaking. The staff was friendly and helpful. The restaurant was pretty good and we loved the live music.

Reviewed on May 17, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $914, price is now $754 per person
$754
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.6/10 Excellent! (879 reviews)
Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!

Reviewed on May 15, 2026

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Stockbridge Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from May 25 to May 26
$143 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Place is beautiful well kept rooms are clean nice sized. My only “complaint” was hot tub area which is fabulous opens at 10am, and we were leaving that day at 9. But that was a very minor inconvenience I will be back next year for sure!"

Reviewed on May 15, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
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
$124 nightly
The price is $136 total per night from May 31 to Jun 1
$136 total
May 31 - Jun 1
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"bosy cream and mouthwash would be nice..there used to be lemon water in the lobby. ty"

Reviewed on May 18, 2026

Comfort Inn Rutland - Killington
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from May 21 to May 22
$121 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (1,187 reviews)
"Excellent hotel, immaculate room and very friendly staff."

Reviewed on May 19, 2026

Align Inn Vermont
See all 2,159 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 $574 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.

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