Stockbridge Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Stockbridge

Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
The price is 3.410.095 ₫ per night from 29 Jun to 30 Jun
3.410.095 ₫
3.751.105 ₫ total
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Great staff, good location a short walk from the historic center. A bit expensive."

Reviewed on 21 Jun 2025

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is 11.210.199 ₫ per night from 6 Jul to 7 Jul
11.210.199 ₫
13.480.983 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on 20 Jun 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 3.276.995 ₫ per night from 29 Jun to 30 Jun
3.276.995 ₫
3.604.695 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"Great service"

Reviewed on 22 Jun 2025

Comfort Inn Rutland - Killington
See all 2,082 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 holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Stockbridge costs! Our packages simplify travel planning and maximise 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 holiday 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 holiday 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 personalise 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Stockbridge holiday as a package?
Expedia holiday 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 customised Stockbridge holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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 accommodation, 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 holiday package that brings all your bookings together.