A person snowboarding down a snowy slope.

Photo by Photo courtesy of Berkshire Visitors Bureau

The Berkshires Romantic Vacations

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  • Discover the most popular places to visit in The Berkshires

    A forested hillside with a clear path and a small building at the top.

    Jiminy Peak Mountain Resort

    Rating: 8.8/10 (311 reviews)

    Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.

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    A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

    Tanglewood Music Center

    Rating: 9.6/10 (457 reviews)

    Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.

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    A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

    Williams College

    Rating: 9.4/10 (534 reviews)

    Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.

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    A calm river surrounded by autumn foliage.

    Photo by Adnan Kakazai

    Norman Rockwell Museum

    Rating: 9.4/10 (347 reviews)

    This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.

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    A building with 'MASS MoCA' written on it, surrounded by greenery and hills.

    Photo by Caminante

    Massachusetts Museum of Contemporary Art

    Rating: 9.4/10 (246 reviews)

    This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.

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    Ski Butternut

    Rating: 9.0/10 (134 reviews)

    Ski Butternut offers 22 diverse trails across 110 acres of terrain suitable for all skill levels. Morning visits reward skiers with freshly groomed slopes and the satisfaction of first tracks.

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    National Shrine of the Divine Mercy

    Rating: 9.0/10 (83 reviews)

    This serene sanctuary in the Berkshire Mountains is a center for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.

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    Lee Premium Outlets

    Rating: 8.2/10 (265 reviews)

    You can find the perfect gifts to bring home at Lee Premium Outlets during your trip to Lee. Amble around the area's gardens or attend a sporting event.

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    Top Romantic The Berkshires Hotels

    Garden Gables

    A modern bedroom with a four-poster bed, a fireplace, and a large floral mural on the wall.
    • Address: 135 Main St, Lenox, MA, 01240, US
    • Location: 15.1 mi from The Berkshires
    • Star rating: 4/5
    • Guest rating: 10/10 (Exceptional, 2 reviews)
    • Price: $188 nightly, $210 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Romantic The Berkshires Hotels
    • Review: The property is in excellent condition and the room was as advertised. Very close to town. Please note, there is no staff on site so everything is self check-in and self service.

    The Yankee Inn

    Two Adirondack chairs facing a river with a forested hill in the background.
    • Address: 461 Pittsfield Rd, Lenox, MA, 01240, US
    • Location: 17.4 mi from The Berkshires
    • Star rating: 2.5/5
    • Guest rating: 9.2/10 (Wonderful, 1004 reviews)
    • Price: $126 nightly, $141 total, Dec 12 - Dec 13, Total with taxes and fees, for Top Romantic The Berkshires Hotels
    • Review: Everything about this place was wonderful! The location, the staff, the cleanliness. The only downsize was we booked this property because of the pool and it was under maintenance during my stay. A notice would have been nice :( Other than that, beautiful inn.

    The Black Swan Lee - Lenox, an Ascend Collection Hotel

    A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
    • Address: 435 Laurel St, Lee, MA, 01238, US
    • Location: 12.1 mi from The Berkshires
    • Star rating: 3/5
    • Guest rating: 9.2/10 (Wonderful, 1002 reviews)
    • Price: $106 nightly, $119 total, Dec 13 - Dec 14, Total with taxes and fees, for Top Romantic The Berkshires Hotels

    Berkshires Untold

    A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
    • Address: 194 Pittsfield Rd, Lenox, MA, 01240, US
    • Location: 16.4 mi from The Berkshires
    • Star rating: 3.5/5
    • Guest rating: 9/10 (Wonderful, 1074 reviews)
    • Price: $106 nightly, $119 total, Nov 17 - Nov 18, Total with taxes and fees, for Top Romantic The Berkshires Hotels

    The Cornell Inn, Lenox & The Berkshires

    A snow-covered outdoor area with a patio, seating, and a covered dining area.
    • Address: 203 Main St, Lenox, MA, 01240, US
    • Location: 15.3 mi from The Berkshires
    • Star rating: 3.5/5
    • Guest rating: 9.4/10 (Exceptional, 1000 reviews)
    • Price: $178 nightly, $198 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Romantic The Berkshires Hotels

    The Red Lion Inn

    A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
    • Address: 30 Main Street, Stockbridge, MA, 01262, US
    • Location: 11.5 mi from The Berkshires
    • Star rating: 3.5/5
    • Guest rating: 8.8/10 (Excellent, 1001 reviews)
    • Price: $197 nightly, $221 total, Nov 22 - Nov 23, Total with taxes and fees, for Top Romantic The Berkshires Hotels

    East Rock Inn

    A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
    • Address: 304 State Rd, Great Barrington, MA, 01230, US
    • Location: 9.9 mi from The Berkshires
    • Star rating: 2/5
    • Guest rating: 9.6/10 (Exceptional, 58 reviews)
    • Price: $115 nightly, $128 total, Dec 15 - Dec 16, Total with taxes and fees, for Top Romantic The Berkshires Hotels

    Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn."
    • Address: 2 Oak Street, West Stockbridge, MA, 01266, US
    • Location: 16.2 mi from The Berkshires
    • Star rating: 2.5/5
    • Guest rating: 9.6/10 (Exceptional, 483 reviews)
    • Price: $145 nightly, $159 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Romantic The Berkshires Hotels
    • Review: Great location for an October getaway. The room was more than comfortable.

    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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    How to find a romantic The Berkshires vacation

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

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    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?

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    How much is a trip for two to The Berkshires?

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    Can I book The Berkshires spa packages for couples?

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    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.

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