Stockbridge Vacations from $430

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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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $535, price is now $430 per person
$430
per person
Apr 1 - Apr 3
found 3 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
The staff was by the staff I mean the one person I saw who checked me. The property is very dated There were mattresses in the stairwell in a very interesting clientele that seemed to linger in the hallways and around the building at all hours of the night The room was fine Nothing to write home about. What was disappointing was the $350 a night that this place charged Granted it was during Leaf season which I was unaware of when made the reservation but in general the facility was tired

Reviewed on Dec 30, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $2,230, price is now $1,570 per person
$1,570
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 out of 5
Price was $1,110, price is now $859 per person
$859
per person
Feb 23 - Feb 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
9/10 Wonderful! (93 reviews)
Wonderful staff, fabulous food, lovely setting! We had a wonderful stay at the Inn over the holidays! Daughter and I had a Spa treatment as well. I also lost a hat on property, the housekeeping staff found it and the Inn mailed it back! 10/10 would recommend!

Reviewed on Jan 7, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,835, price is now $1,440 per person
$1,440
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
No reviews
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,427, price is now $1,128 per person
$1,128
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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 (1,003 reviews)
We always stay here and it’s always great.

Reviewed on Jan 5, 2026

White River Inn and Suites
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
$140 nightly
The price is $154 total per night from Feb 1 to Feb 2
$154 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
Check-in was quick and easy.

Reviewed on Jan 5, 2026

Comfort Inn Rutland - Killington
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 21 to Jan 22
$189 total
Jan 21 - Jan 22
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Amenities are great!

Reviewed on Dec 29, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 2,119 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 $430 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.