Stockbridge Holidays

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Top hotels in Stockbridge

The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is S$319 per night from 13 Aug to 14 Aug
S$319
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Live the front porch and dining room. We were first assigned a room in the Steven’s bldg. it was completely not up to standards. Musty smell , far from hotel and old dirty furniture. I complained to the front desk and was upgraded to a nicer building. Staff very cooperative. The pool was cloudy and ..."

Reviewed on 13 Jul, 2025

The Red Lion Inn
Tanglewood Suites

Tanglewood Suites

2.5 out of 5
MA-102, Stockbridge, MA
The price is S$345 per night from 17 Jul to 18 Jul
S$345
17 Jul - 18 Jul
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
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
The price is S$676 per night from 21 Jul to 22 Jul
S$676
21 Jul - 22 Jul
includes taxes & fees
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on 27 Jul, 2024

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
See all 1,367 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.