Stockbridge Vacations from $578

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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.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $678, price is now $578 per person
$578
per person
Jun 26 - Jun 29
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
I’ve stayed here with my two daughters multiple times and it’s always incredible.

Reviewed on May 17, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $836, price is now $639 per person
$639
per person
Jun 26 - Jun 29
found 10 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.4/10 Exceptional! (926 reviews)
The condo was spacious and well equipped. The continental breakfast was convenient. The views of the lake are breathtaking. The staff was friendly and helpful. The restaurant was pretty good and we loved the live music.

Reviewed on May 17, 2026

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $871, price is now $687 per person
$687
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Lebanon (LEB)
9.4/10 Exceptional! (443 reviews)
Very clean hotel and helpful staff Didn’t love the ice maker in the freezer in the room would have preferred a hallway ice maker.

Reviewed on May 18, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $969, price is now $800 per person
$800
per person
Jun 27 - Jul 1
found 10 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
8.8/10 Excellent! (926 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants

Reviewed on May 12, 2026

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,121, price is now $957 per person
$957
per person
Jul 26 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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
$122 nightly
The price is $134 total per night from May 25 to May 26
$134 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (1,001 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
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
$133 nightly
The price is $146 total per night from May 28 to May 29
$146 total
May 28 - May 29
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"bosy cream and mouthwash would be nice..there used to be lemon water in the lobby. ty"

Reviewed on May 18, 2026

Comfort Inn Rutland - Killington
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $118 total per night from May 21 to May 22
$118 total
May 21 - May 22
Total with taxes and fees
9.4/10 Exceptional! (1,192 reviews)
"Older motel style place that has been nicely redone. Very clean and sleek. Rooms are large and well appointed. Breakfast good. Plenty of choices"

Reviewed on May 19, 2026

Align Inn Vermont
See all 2,166 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 $578 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.