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.
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
Price was $805, price is now $634 per person
$634
per person
Dec 5 - Dec 10
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
9.4/10 Exceptional! (37 reviews)
The owner was delightful and very accommodating.

Reviewed on Oct 28, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
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

Stone Hearth Inn and Eatery

3 out of 5
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

Chalet 239

Chalet 239

2 out of 5
Price was $1,202, price is now $932 per person
$932
per person
Dec 29 - Jan 3
found 5 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
9.4/10 Exceptional! (80 reviews)
Great place for a quick trip to VT!

Reviewed on Oct 21, 2025

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Stockbridge Hotel Deals

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
$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

Comfort Inn Rutland - Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
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

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
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

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 2,067 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 $634 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.