Stockbridge Vacations from $695

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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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $891, price is now $695 per person
$695
per person
Feb 12 - Feb 15
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Lebanon (LEB)
18/10 Exceptional! (774 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.

Reviewed on Nov 18, 2025

Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $2,590, price is now $2,052 per person
$2,052
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
16/10 Exceptional! (31 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $2,505, price is now $1,989 per person
$1,989
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
17.6/10 Exceptional! (25 reviews)
Room was clean, spacious and quiet. We had an amazing view and were warmly greeted by the staff. Upon check-in we were informed that they were proactively moving our stay to another building because of problems that had been reported. Thankful for their foresight so we didn't have to endure any issues whatsoever! Check-in and parking were extremely easy with the instructions provided via email. Would definitely recommend a stay at the Jackson Gore Building.

Reviewed on Oct 28, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,327, price is now $1,856 per person
$1,856
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
17.2/10 Exceptional! (834 reviews)
Room was very clean and comfortable. Loved having the fireplace. Indoor parking garage was a plus with easy access to our room. We enjoyed dinner and breakfast at the restaurant. The outdoor space was fabulous with many activities.

Reviewed on Nov 14, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,232, price is now $983 per person
$983
per person
Feb 12 - Feb 15
found 6 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
14.8/10 Exceptional! (1,003 reviews)
Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!

Reviewed on Nov 5, 2025

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Stockbridge Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (551 reviews)
Clean room, Awesome staff and always a good vibe.

Reviewed on Nov 17, 2025

Woodstock Inn & Resort
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
$116 nightly
The price is $128 total per night from Dec 10 to Dec 11
$128 total
Dec 10 - Dec 11
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
The breakfast menu was a highlight. It was very exciting to see that there were waffle makers. Parking definitely felt safe, but it was not very easy. The room was clean. The staff was super friendly and helpful. There are snacks in the lobby. They have bubblers for regular water and lemon water ...

Reviewed on Nov 21, 2025

Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
$147 nightly
The price is $161 total per night from Nov 30 to Dec 1
$161 total
Nov 30 - Dec 1
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Great staff and a beautiful place to stay

Reviewed on Nov 17, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 2,096 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 $695 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.