Stockbridge Vacations from $495

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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.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $612, price is now $495 per person
$495
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.2/10 Wonderful! (412 reviews)
Great experiment. Very accommodating stuff and environment.

Reviewed on Nov 29, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $715, price is now $555 per person
$555
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Lebanon (LEB)
9/10 Wonderful! (774 reviews)
Clean room, very nice staff, everything was excellent!

Reviewed on Dec 11, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,138, price is now $902 per person
$902
per person
Feb 12 - Feb 15
found 13 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Wonderful experience definitely would stay again.

Reviewed on Dec 16, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $899, price is now $722 per person
$722
per person
Mar 5 - Mar 9
found 6 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
The staff was super nice and flexible! Location was great

Reviewed on Dec 13, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,431, price is now $1,155 per person
$1,155
per person
Mar 5 - Mar 9
found 6 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.

Reviewed on Nov 30, 2025

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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
$211 nightly
The price is $232 total per night from Jan 12 to Jan 13
$232 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
7.2/10 Good! (1,006 reviews)
Hotel staff was top shelf!!! Ate at the bar. Flatbread was great! And beer was ice cold !!! Great hotel definitely will stay here again!!

Reviewed on Dec 15, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from Jan 19 to Jan 20
$395 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
9.2/10 Wonderful! (556 reviews)
I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit.

Reviewed on Dec 13, 2025

Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$272 nightly
The price is $299 total per night from Dec 23 to Dec 24
$299 total
Dec 23 - Dec 24
Total with taxes and fees
9/10 Wonderful! (961 reviews)
Staff was very friendly and helpful. Room was clean. On site restaurant was wonderful.

Reviewed on Dec 15, 2025

The Mountain Inn at Killington
See all 2,120 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 $495 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.