The Berkshires Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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4 Night Romantic vacations in The Berkshires
Jiminy Peak Mountain Resort
Reviewed on May 23, 2026
Vacation Village in the Berkshires
Reviewed on May 31, 2026
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.
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 $551. 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.
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
"Shaker Inn is a comfortable cozy inn in the village of West Stockbridge. Check in was easy, room was comfortable, clean, grounds were well-maintained and lovely. Village of West Stockbridge was only a couple of blocks away. We were able to walk to restaurant for dinner. Staff were easily available ..."
Reviewed on Jun 1, 2026
Vacation Village in the Berkshires
"Great place just listed again for four more nights"
Reviewed on Jun 3, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Couples like: onsite spa services, bar, winery tours
"Hi, for the most part, my stay was fantastic. The staff were excellent. Breakfast was awesome! The Restaurant and Bar were great! My one negative comment is about the lack of hot water in the morning for me to take a shower. Very disappointing. I am coming back there the next 2 weeks and I hope that ..."
Reviewed on Jun 4, 2026
