Stockbridge Vacations from $503
Book a Hotel + Flight or Car together to unlock savings
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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$503
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
Vikings Villages Resort
$678
per person
Oct 1 - Oct 4
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
10/10 Exceptional! (227 reviews)
Viking Village was such a unique and enjoyable stay! It was impeccable, every detail (and there were a lot of very fine ones) was perfectly executed. Very comfortable, quiet, and felt much more luxurious than we are used to as budget travelers. Every amenity was quality and in working condition, we especially appreciated the fireplace. Beautiful scenery and wildlife. No notes, everything was perfect!
Reviewed on Aug 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Stockbridge
View all tripsStay near popular Stockbridge attractions
Belcher Library
After visiting Belcher Library, make a plan to see the other sights and activities in Gaysville.
Les Newell Wildlife Management Area
You can take time to visit Les Newell Wildlife Management Area during your travels to Stockbridge.
Stockbridge Hotel Deals
Align Inn Vermont
5817 Woodstock Rd Quechee VT
$117 nightly
$128 total
Aug 30 - Aug 31
Total with taxes and fees
9.4/10 Exceptional! (1,302 reviews)
"Great staff, friendly, helpful, available. Best breakfast, Real food! Place is clean. In need of updating, tub paint peeling, 1980 feel or late 1970. Pool nice, perfect temperature! Bed good. Quiet and we were there when they were full!"
Reviewed on Aug 27, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$449 nightly
$494 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (599 reviews)
"Amazing! Will visit again."
Reviewed on Aug 7, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$146 nightly
$161 total
Aug 30 - Aug 31
Total with taxes and fees
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 $503 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.