Stockbridge Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Stockbridge

The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is 4.938.759 ₫ per night from 25 Jun to 26 Jun
4.938.759 ₫
6.684.128 ₫ total
25 Jun - 26 Jun
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"I had excellent stay at the Red Lion Inn"

Reviewed on 16 Jun 2025

The Red Lion Inn
Tanglewood Suites
Tanglewood Suites
2.5 out of 5
MA-102, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is 7.029.239 ₫ per night from 23 Jun to 24 Jun
7.029.239 ₫
7.029.239 ₫ total
23 Jun - 24 Jun
includes taxes & fees
Like a stay at granny’s house
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, ..."

Reviewed on 19 Feb 2024

Tanglewood Suites
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is 2.848.279 ₫ per night from 23 Jun to 24 Jun
2.848.279 ₫
3.181.528 ₫ total
23 Jun - 24 Jun
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Clean, quiet hotel in Great Barrington. Staff members were kind and attentive. Easy parking and check in / check out."

Reviewed on 17 Jun 2025

Quality Inn
See all 1,363 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?
You can grab a holiday package to this popular destination on Expedia. However, how much your holiday to Stockbridge costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Stockbridge?
If you're hoping to snag a cheap Stockbridge holiday package, consider travelling in January, February and March. You'll usually find lower prices on flights and hotels during these quieter months --- perfect for budget-conscious travellers.
How many days is enough for Stockbridge?
Usually, a handful of days is enough to explore the major sights during your Stockbridge holiday. But if you want to have time to kick back or go on day tours, consider extending your itinerary.
Is it worth booking a holiday package to Stockbridge?
Stockbridge is a good holiday destination with attractions like National Shrine of the Divine Mercy among the many things to keep you entertained. Whether you're travelling with the family or getting away with friends, a Stockbridge holiday promises fun for everyone.
How to find the best Stockbridge package deals?
Use Expedia's filter tool to help you find some terrific Stockbridge package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Stockbridge package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Stockbridge holiday as a package?
You can enjoy significant savings on your Stockbridge break by booking a customised holiday package. Click on the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Stockbridge?
Secure amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Stockbridge trip.
How to plan a trip to Stockbridge?

  1. Choose when to travel: Check your calendar and pack your bags. Your favourite time of year and the type of activities on offer will also help you decide when to escape to Stockbridge.
  2. Set your budget: Factor in expenses such as flights, meals and transportation when calculating how much to put aside for your trip to Stockbridge. Then, choose a hotel that works with your budget, whether that's an affordable stay or a lavish getaway.
  3. Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Stockbridge. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customised Stockbridge holiday package.

Popular places to visit

Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

Berkshire Botanical Garden

Explore the great outdoors at Berkshire Botanical Garden, a lovely green space in Stockbridge. While you're in the area, stroll along the lakeside.

Berkshire Botanical Garden

Berkshire Theatre Festival

You can enjoy a show at Berkshire Theatre Festival during your trip to Stockbridge. Wander the lakeside in this quaint area.

Berkshire Theatre Festival