
Stockbridge Vacations from $634
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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 Shire Woodstock
Save 100% on your flight
Price was $1,574, price is now $1,107 per person
$1,107
per person
Dec 12 - Dec 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
8.8/10 Excellent! (851 reviews)
This property does not look like the pictures online. It was clean and had a great location, but past that, it was just an older motel that had been painted and cleaned up. There was no real lobby or check-in desk. They offered coffee in the morning, but it was broken the day we stayed. The view on the back side was pretty, but I really felt like we were in a 2 star motel. No extra amenities, and the furniture looked like it was all from a thrift store; worn out and needed updating. I was hoping for the cost to find it as beautiful as it is in the photos online. The staff was friendly and the room was clean. Note, the hotel room door opens to the outside. There was no interior hallway to our room. This made it feel a little unsafe for two women traveling alone.
Reviewed on Oct 27, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Save 100% on your flight
Price was $992, price is now $727 per person
$727
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Lebanon (LEB)
9/10 Wonderful! (759 reviews)
Very nice place a room. We were disappointed that both restaurants at the place were closed. Had to drive to another small town as there was nothing in this remote area within 10 miles. The recommended nearby deli that was recommended by staff had closed early on a Tuesday afternoon @4pm.
Reviewed on Oct 23, 2025

Stone Hearth Inn and Eatery
Price was $1,069, price is now $806 per person
$806
per person
Dec 5 - Dec 10
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
9.2/10 Wonderful! (100 reviews)
The owner was so nice, and the chef made delicious dishes. Highly recommend!
Reviewed on Oct 13, 2025

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Comfort Inn Rutland - Killington
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from Nov 11 to Nov 12
$121 total
Nov 11 - Nov 12
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
The front desk ladies showed best customer service.
Reviewed on Oct 26, 2025

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$389 nightly
The price is $428 total per night from Nov 16 to Nov 17
$428 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (540 reviews)
Highly recommend stay here
Reviewed on Oct 24, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Nov 2 to Nov 3
$143 total
Nov 2 - Nov 3
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
very nice place
Reviewed on Oct 22, 2025
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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