The Berkshires Romantic Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau
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How to find romantic The Berkshires holiday packages on Expedia?

How can I book a romantic getaway in The Berkshires?

Find your dream romantic The Berkshires getaway on Expedia. From secluded hideaways to blissful spa treatments and charming country escapes, we’ve got it all. Just activate our “romantic” filters to uncover your ideal couple’s retreat in The Berkshires.

How can I find cheap The Berkshires romantic holidays?

Unveil the perfect and budget-friendly romantic getaways in The Berkshires with Expedia. Our filters unlock countless options, ensuring a heart-pounding experience. Set budget filters to match your spending limits and sort by price to prioritise the most affordable options in your search results.

How can I select a romantic couple’s package for The Berkshires?

In your search, you can apply search filters for The Berkshires trip packages and sort your results to see the romantic getaway options first. With those standards, you could find amazing romantic holiday options in The Berkshires, from winter getaways to secluded country or budget beach holidays with your loved one.

How can I find excellent romantic The Berkshires holiday deals?

Plan your ultimate couple’s getaway in The Berkshires with our user-friendly search tools. Opt for a hotel suite with a view worth sharing on Instagram. Cruise with the top down and feel the warm breeze in your hair with a luxury car hire. Decide on a romantic couple’s spa treatment, a beachfront candle-lit dinner, or a glamorous night out on the town.

How can I find last-minute romantic holiday deals to The Berkshires using Expedia?

For last-minute romantic holiday package deals in The Berkshires, enter your travel dates into the search and discover available deals. Customise your search with filters, covering amenities, price, star rating, and more to find your ideal romantic package for couples.

How can I find pet-friendly romantic getaway packages in The Berkshires?

Refine your search with the “pet-friendly” filter to discover top pet-welcoming hotels and resorts in The Berkshires. Experience a couple’s treatment, bask in beautiful surroundings, and revel in a pampering romantic getaway, knowing your pet is either by your side or well cared for in doggy day care.

How can I find great weekend couple’s holiday packages The Berkshires?

Escape the weekly grind with fantastic couple’s weekend getaways in The Berkshires. Enter your location and date preferences in your Expedia search and let us reveal hidden gems to leave you refreshed and love-struck for the week ahead.

Where can I find the most luxurious couple’s holiday packages in The Berkshires?

Discover the ultimate luxury romantic packages in The Berkshires with ease. Use the site’s or app’s search function to explore a range of lavish options, as well as to refine your choices by star rating and price.

Why should book I my romantic The Berkshires holiday with Expedia?

Choose from our latest incredible deals or customise your trip in just a few clicks, with simple search and filter functions that make finding your next romantic The Berkshires getaway easy. Plus, booking a package with Expedia could save you money, too, making a The Berkshires holiday for couples all the more attractive.

Top Romantic The Berkshires Hotels

Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
  • 25 min walk from Tanglewood Music Center
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...
9.6/10 Exceptional! (389 reviews)
"Well appointed room w lots of amenities. Good parking, friendly staff, easy check-in :)"

Reviewed on 29 Jul. 2025

Shaker Mill Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 35 min drive from Tanglewood Music Center
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,912 reviews)
"My husband and I stayed here for the last section of our vacation. The property was excellent-very clean & very quiet. Only thing was all parking was on gravel and on an angle so hard to find a safe spot for our motorcycle."

Reviewed on 29 Jul. 2025

Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
  • 16 min drive from Tanglewood Music Center
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (838 reviews)
"Convenient for our trip"

Reviewed on 27 Jul. 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.