Stockbridge Vacations from $532

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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 $651, price is now $532 per person
$532
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Fantastic! Easy check in and out! Rooms were updated and spotless. Great customer service!

Reviewed on Jan 17, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,536, price is now $1,171 per person
$1,171
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $792, price is now $636 per person
$636
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
It is an accommodation with the most beautiful view. It is very convenient because there is a shop in front of the accommodation.

Reviewed on Jan 17, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,103, price is now $901 per person
$901
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Solid accommodations.

Reviewed on Jan 12, 2026

Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $3,152, price is now $2,604 per person
$2,604
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews
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Stockbridge Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$429 nightly
The price is $472 total per night from Jan 21 to Jan 22
$472 total
Jan 21 - Jan 22
Total with taxes and fees
9.2/10 Wonderful! (560 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

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

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
$171 nightly
The price is $189 total per night from Jan 28 to Jan 29
$189 total
Jan 28 - Jan 29
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
Solid accommodations.

Reviewed on Jan 12, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $132 total per night from Jan 21 to Jan 22
$132 total
Jan 21 - Jan 22
Total with taxes and fees
9.4/10 Exceptional! (1,075 reviews)
Clean, quiet, good breakfast. Check in was easy and staff was friendly.

Reviewed on Jan 15, 2026

Align Inn Vermont
See all 2,147 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 $532 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.