Stockbridge Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.

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
7.2/10 Good! (1,000 reviews)
Great place to stay. Highly recommended.
"This was a wonderful stay. Everyone, from front desk check in, to bartender, to Starbucks barista were warm, inviting, friendly, and helpful. The room was spotless. Appointed as advertised, and well cared for each day. I was pleasantly surprised and impressed overall."

Reviewed on May 19, 2024

Get rates
Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square
Comfort Inn Trolley Square
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,001 reviews)
"No USB"

Reviewed on Apr. 29, 2024

Get rates
Comfort Inn Trolley Square
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
9.2/10 Wonderful! (441 reviews)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."

Reviewed on May 3, 2024

Get rates
Woodstock Inn & Resort
See all 1,912 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Stockbridge vacation package cost?
Handcraft your Stockbridge package from as little as . Pick from any combination of flights, hotels and rental cars to build the getaway you’ve been dreaming about for ages. Remember to add on one or two experiences!
How do I get a cheap travel package to Stockbridge?
Bundle your hotel and flight bookings, throw in extras such as activities, and save with a Stockbridge vacation package. You won’t just pick up exciting discounts on your escape — you’ll have loads of choice at your fingertips too. When you book through Expedia, you can choose from more than 550 air carriers and 1,000,000 hotels all over the world. Your next affordable adventure begins right here, right now!
What are the top hotels in Stockbridge?
If it’s comfort and convenience you’re searching for, you can’t go past Cozy, Charming Vermont Chalet Close To 5 Major Ski Areas. Spend your nights kicking back here and your days discovering Stockbridge’s most well-known attractions.
How far in advance should I book my Stockbridge vacation?
To bag discount prices, book early. Airlines generally release flight tickets, along with some of the lowest fares, nearly 12 months in advance. Hotels, car rental and activities should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway in Stockbridge, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia Stockbridge travel package include?
With Expedia, you can select any combination of hotels, car rentals and flights to create your perfect Stockbridge package. Once you’ve made your booking, you can add on the fun things like tours and experiences. Remember — the more you bundle, the more you stand to save!
What should I know before booking a Stockbridge travel package?
So many places to travel to, so many things to see. With a travel package, you’ll be able to cross more of them off your list. Combine your hotels, flights and rental cars and make big savings.
Can I choose my airline with a Stockbridge Expedia vacation package?
The choice is all yours! We offer more than 550 airlines across the globe, so you can tailor your Stockbridge vacation according to your budget and travel needs.
If I'm not able to travel, can I cancel my Stockbridge vacation package?
Because we know life can be unpredictable, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you’ve booked your Stockbridge vacation package in the last 24 hours, you may be able to cancel or change it free of charge. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.