Stockbridge Vacations from $714

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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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $905, price is now $714 per person
$714
per person
Jan 24 - Jan 27
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9.2/10 Wonderful! (941 reviews)
Great place to stay!

Reviewed on Dec 2, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,685, price is now $1,209 per person
$1,209
per person
Feb 12 - Feb 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
No reviews
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,732, price is now $1,356 per person
$1,356
per person
Feb 12 - Feb 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
No reviews
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $933, price is now $739 per person
$739
per person
Feb 12 - Feb 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.

Reviewed on Nov 18, 2025

Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $2,224, price is now $1,774 per person
$1,774
per person
Feb 12 - Feb 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Springfield (VSF)
8.8/10 Excellent! (25 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

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Stockbridge Hotel Deals

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $120 total per night from Jan 4 to Jan 5
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
6.8/10 (1,002 reviews)
It was good.

Reviewed on Dec 6, 2025

White River Inn and Suites
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
$188 nightly
The price is $206 total per night from Dec 14 to Dec 15
$206 total
Dec 14 - Dec 15
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
Clean room and bathroom. Alex at the desk was very helpful and nice.

Reviewed on Dec 5, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$261 nightly
The price is $288 total per night from Dec 14 to Dec 15
$288 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (956 reviews)
We had a great weekend stay. Staff was great. We had a nice clean room, the continental breakfast had a great selection and the restaurant was really nice, food was delicious and so very convenient. We really enjoyed sitting by the fire in the lounge type room. And although we didnt bring our dog ...

Reviewed on Dec 5, 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 $714 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.