Stockbridge Vacations from $698

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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.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $908, price is now $698 per person
$698
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
No reviews
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Save 100% on your flight
Price was $1,341, price is now $888 per person
$888
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (93 reviews)
Will definitely be back!!

Reviewed on Apr 5, 2026

Chateau Rooms

Chateau Rooms

4.5 out of 5
Save 100% on your flight
Price was $3,095, price is now $2,322 per person
$2,322
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (66 reviews)
Such a beautiful time, So clean, and cozy. Such a beautiful, peaceful, and romantic place. Very enchanting, and the owner is so kind, and caring. Def cant wait to go back again.

Reviewed on Jan 4, 2026

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $977, price is now $789 per person
$789
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
6.6/10 (1,015 reviews)
The hotel was reasonably well maintianed and had a decent breakfast bar.

Reviewed on May 24, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,210, price is now $1,009 per person
$1,009
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
10/10 Exceptional! (113 reviews)
Convenient location with food, brewery, & park nearby. Close to Burlington yet away from the crowds. Breakfast buffet was varied and very good. Common areas have a chill vibe. Host was welcoming. Place was super clean. Bed was comfortable. Would like to visit again with more time to explore the area.

Reviewed on May 9, 2026

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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
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $161 total per night from May 28 to May 29
$161 total
May 28 - May 29
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Place is beautiful well kept rooms are clean nice sized. My only “complaint” was hot tub area which is fabulous opens at 10am, and we were leaving that day at 9. But that was a very minor inconvenience I will be back next year for sure!"

Reviewed on May 15, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$119 nightly
The price is $131 total per night from May 28 to May 29
$131 total
May 28 - May 29
Total with taxes and fees
9.4/10 Exceptional! (1,198 reviews)
"The room was very clean and well upkept. Breakfast was great, The only complaint we had was that we took our showers with cold water as there was no hot water. When we spoke to the front desk the answer was, "oh you could of used the shower in the pool room". It seems as though we should of received ..."

Reviewed on May 26, 2026

Align Inn Vermont
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
$135 nightly
The price is $149 total per night from Jun 21 to Jun 22
$149 total
Jun 21 - Jun 22
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
"Free parking, clean room."

Reviewed on May 25, 2026

Comfort Inn Rutland - Killington
See all 2,159 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 $698 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.