Stockbridge Trips (flight + hotel)

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Top hotels in Stockbridge

Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is P6,928 per night from Jun 22 to Jun 23
P6,928
P7,621 total
Jun 22 - Jun 23
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The staff were very friendly , well informed and helpful"

Reviewed on Jun 20, 2025

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is P24,643 per night from Jul 6 to Jul 7
P24,643
P29,635 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on Jun 20, 2025

Woodstock Inn & Resort
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
The price is P7,496 per night from Jun 23 to Jun 24
P7,496
P8,246 total
Jun 23 - Jun 24
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Quiet and comfortable"

Reviewed on Jun 16, 2025

Comfort Inn Rutland - Killington
See all 2,087 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.

Frequently asked questions

How much does a Stockbridge vacation package cost?
Offering great value package deals 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?
The off-season is the best time to head to Stockbridge if you're on a budget. Another tip for scoring cheap Stockbridge vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Stockbridge?
The ideal length for your Stockbridge vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to check out all the major attractions and explore some hidden treasures along the way.
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.
How to plan a trip to Stockbridge?

  1. Pick your travel dates: The things you'd like to do in Stockbridge and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: On top of the price of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Stockbridge.
  3. Decide how many days away: Start by listing all the sights and activities you'd like to get to in Stockbridge. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Stockbridge vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.