Title: The Berkshires Romantic Vacations 2026 | Expedia.com

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# The Berkshires Romantic Vacations

## Book a Romantic Hotel + Flight or Car together to unlock savings

Photo by Photo courtesy of Berkshire Visitors Bureau

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## How to find a romantic The Berkshires vacation

####  How can I find the best The Berkshires vacation packages for couples? 

 To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing. 

####  How can I find cheap The Berkshires romantic packages for two? 

 For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of . 

####  How can I plan a great romantic trip to The Berkshires? 

 Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two. 

####  How much is a trip for two to The Berkshires? 

 Put a price on love with stunning deals for duos starting at just . Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply. 

####  Can I book The Berkshires spa packages for couples? 

 Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match. 

####  What’s the best time of year for a romantic vacation in The Berkshires? 

 Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience. 

####  How can I book romantic weekend getaway packages in The Berkshires? 

 To book a loved-up break in The Berkshires, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation). 

####  Can I book a romantic trip to The Berkshires with free cancellation and/or flexible dates? 

 The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options. 

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

 If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection? 

## Top Romantic The Berkshires Hotels

![Shaker Mill Inn](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Shaker Mill Inn

2 Oak Street West Stockbridge MA

- 37 min drive from Jiminy Peak Mountain Resort

Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...

9.6/10 Exceptional! (415 reviews)

Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key).

Reviewed on Jan 13, 2026

[](https://expedia.com/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information)

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

- 13 min walk from Jiminy Peak Mountain Resort

A garden and in-room fireplaces await at this romantic condo, which also offers a terrace and an outdoor pool.

8.6/10 Excellent! (2,227 reviews)

Spacious 2 bed 2 bath!

Reviewed on Feb 3, 2026

[](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

- 18 min drive from Jiminy Peak Mountain Resort

A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.

8/10 Very Good! (1,001 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

generally good

Reviewed on Jan 19, 2026

[](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

[See all 1,088 properties in The Berkshires](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6047665)

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.

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## More Vacation Ideas

[Flights to The Berkshires

](https://expedia.com/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[

The Berkshires Hotels

](https://expedia.com/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[

Vacation Rentals in The Berkshires

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Car Rentals in The Berkshires

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

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