Photo by Photo courtesy of Berkshire Visitors Bureau
Open Photo by Photo courtesy of Berkshire Visitors Bureau
The Berkshires Romantic Vacations
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Top Romantic vacation packages in The Berkshires
Price found within the past 48 hours. Click for updated prices.
- The Yankee Inn
Oct 10 - Oct 15The Yankee Inn + Flight
Lenox5 nights2.5 star property9.2/10 - Wonderful (1,000 reviews)"I would stay here again for sure. Nice clean room, generous breakfast, pool and hot tub, what’s not to like? Very convenient to Bousquet ski area. Restaurants nearby. Easy drive into either Lenox or Pittsfield."Reviewed July 28, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - EWR • Nonstop EWR - ATL • Nonstop - Berkshires Untold
Oct 15 - Oct 18Berkshires Untold + Flight
Lenox3 nights3.5 star property9.0/10 - Wonderful (1,029 reviews)"Rooms where rather small, but Adequate. The location was good. Mainly a typical hotel"Reviewed July 30, 2026Roundtrip • New York (NYC) - Albany (ALB)LGA - ALB • Nonstop ALB - LGA • Nonstop$815$672found 23 hours agoper traveler - Gateways Inn & Restaurant
Oct 15 - Oct 18Gateways Inn & Restaurant + Flight
Lenox3 nights3.0 star property8.0/10 - Very Good (201 reviews)"Good location, beautiful inn. We had a claw tub with hand held shower only. Breakfast was delicious and great choices. Roo. Temp easy to adjust. No USB plugs or convenient outlet near bed. TV was rather small on a dresser. Two nice chairs in room. Good space overall."Reviewed July 17, 2026Roundtrip • New York (NYC) - Albany (ALB)LGA - ALB • Nonstop ALB - LGA • Nonstop$1,002$858found 23 hours agoper traveler - The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Oct 15 - Oct 18The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood + Flight
Stockbridge3 nights4.5 star property9.2/10 - Wonderful (114 reviews)"Very lovely beautiful Room and property The outside pool was not available"Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - JFK • Nonstop EWR - ATL • Nonstop$1,052$908found 1 day agoper traveler - The Red Lion Inn
Oct 15 - Oct 18The Red Lion Inn + Flight
Stockbridge3 nights3.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Atlanta (ATL) - Albany (ALB)ATL - JFK • Nonstop EWR - ATL • Nonstop$860$761found 1 day agoper traveler
Discover the most popular places to visit in The Berkshires
Photo by Caminante
Open Photo by Caminante
Massachusetts Museum of Contemporary Art
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.
Photo by Caitlin Reese
Open Photo by Caitlin Reese
Mount Greylock
9.4/10 (180 reviews)
Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.
Top Romantic The Berkshires Hotels
9.2 out of 10, Wonderful, (1,000 reviews)
9.2/10
Wonderful
(1,000 reviews)
"First class staff and wonderful breakfast."
$154 nightly
The price is $172
$172 total
Aug 2 - Aug 3
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG2.5 star property
10.5 mi from The Berkshires
8.8 out of 10, Excellent, (796 reviews)
8.8/10
Excellent
(796 reviews)
"It’s very outdated and shower curtain did not work and room had musty smell"
$146 nightly
The price is $163
$163 total
Aug 30 - Aug 31
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires3.0 star property
10.5 mi from The Berkshires
9.4 out of 10, Exceptional, (799 reviews)
9.4/10
Exceptional
(799 reviews)
$195 nightly
The price is $217
$217 total
Aug 10 - Aug 11
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel3.0 star property
36.8 mi from The Berkshires
8.8 out of 10, Excellent, (1,002 reviews)
8.8/10
Excellent
(1,002 reviews)
$161 nightly
The price is $179
$179 total
Aug 23 - Aug 24
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
12.1 mi from The Berkshires
9.0 out of 10, Wonderful, (1,000 reviews)
9.0/10
Wonderful
(1,000 reviews)
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South2.5 star property
10.4 mi from The Berkshires
8.4 out of 10, Very Good, (1,001 reviews)
8.4/10
Very Good
(1,001 reviews)
$120 nightly
The price is $134
$134 total
Aug 24 - Aug 25
Total with taxes and fees
9.6 out of 10, Exceptional, (881 reviews)
9.6/10
Exceptional
(881 reviews)
$219 nightly
The price is $245
$245 total
Aug 2 - Aug 3
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires3.0 star property
16 mi from The Berkshires
9.2 out of 10, Wonderful, (643 reviews)
9.2/10
Wonderful
(643 reviews)
"Helpful staff, clean room and great facilities."
$212 nightly
The price is $236
$236 total
Aug 19 - Aug 20
Total with taxes and fees
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.
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.
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 $532. 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?