Stockbridge Vacations from $628

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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 Vermont Inn

The Vermont Inn

3 out of 5
Price was $778, price is now $628 per person
$628
per person
Feb 19 - Feb 22
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (412 reviews)
Great experiment. Very accommodating stuff and environment.

Reviewed on Nov 29, 2025

Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Price was $935, price is now $694 per person
$694
per person
Feb 18 - Feb 22
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Lebanon (LEB)
9.6/10 Exceptional! (886 reviews)
The perfect location for visiting my son at Dartmouth! He was able to walk over for breaks during classes and even chose to spend a few nights. The hotel is inviting and comfortable, the staff welcoming. Highly recommend!

Reviewed on Jan 17, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,823, price is now $1,353 per person
$1,353
per person
Feb 19 - Feb 22
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $896, price is now $700 per person
$700
per person
Feb 18 - Feb 22
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
It is an accommodation with the most beautiful view. It is very convenient because there is a shop in front of the accommodation.

Reviewed on Jan 17, 2026

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,664, price is now $2,121 per person
$2,121
per person
Feb 18 - Feb 22
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 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
$113 nightly
The price is $124 total per night from Feb 8 to Feb 9
$124 total
Feb 8 - Feb 9
Total with taxes and fees
6.8/10 (1,001 reviews)
Great hotel! Beautiful area

Reviewed on Jan 12, 2026

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
$171 nightly
The price is $189 total per night from Jan 28 to Jan 29
$189 total
Jan 28 - Jan 29
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Solid accommodations.

Reviewed on Jan 12, 2026

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 Jan 20 to Jan 21
$288 total
Jan 20 - Jan 21
Total with taxes and fees
9.2/10 Wonderful! (980 reviews)
Check in service Breakfast

Reviewed on Jan 14, 2026

The Mountain Inn at Killington
See all 2,132 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 $628 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.