Stockbridge Vacations from $808

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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
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (403 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (791 reviews)
The Air Conditioning unit was waking me up every time it started up. Room 225. That is my only inconvenience. Everything else was wonderful.

Reviewed on Aug 1, 2025

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Lebanon (LEB)
9.4/10 Exceptional! (217 reviews)
Wonder stay. Clean and very comfortable

Reviewed on Jul 28, 2025

The Vesper

The Vesper

3 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
9.2/10 Wonderful! (24 reviews)
Charming quaint place with artistic decor. Care was taken with the breakfast - delicious, homemade and wonderful presentation. It felt very homey. Prompt response to my texts; excellent communication. Welcoming and friendly. I would definitely stay here again and recommend the Vesper highly.

Reviewed on Jul 17, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
7.2/10 Good! (1,001 reviews)
Views were spectacular

Reviewed on Jul 16, 2025

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Stockbridge Hotel Deals

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
$125 nightly
The price is $138 total per night from Aug 18 to Aug 19
$138 total
Aug 18 - Aug 19
Total includes taxes and fees
8/10 Very Good! (1,000 reviews)
"Great location."

Reviewed on Jul 31, 2025

Comfort Inn Rutland - Killington
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
$127 nightly
The price is $139 total per night from Aug 10 to Aug 11
$139 total
Aug 10 - Aug 11
Total includes taxes and fees
7/10 Good! (1,003 reviews)
"Excellent location! Staff were really friendly."

Reviewed on Jul 30, 2025

White River Inn and Suites
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (530 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
See all 2,075 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.

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Frequently asked questions

How much does a Stockbridge vacation package cost?
Offering great value package deals from $808 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.