Berkshires is the perfect destination for couples looking to indulge in a romantic getaway, be it on the weekdays or during the weekends. One of the most well-known romantic attractions in Berkshires is Mount Greylock State Reservation. Whether you come during spring, summer or any other season, you will have plenty of things to see and do. You can try camping and snowmobiling with abundant opportunities to reconnect with nature here. More religious couples can pay a visit to the nearby National Shrine of The Divine Mercy. You can participate in a healing mass and absorb a peaceful atmosphere at the church. Berkshires also provides an array of wonderful yet romantic destinations to choose from. Scroll down to learn more about the best romantic getaways in Berkshires, Massachusetts.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to couple-friendly amenities and activities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 27, 2025.
1. Lenox (from USD 226)
To get from Berkshires to Lenox, it takes just about 17 minutes by car to cover the distance of 10.3 miles (16.58 kilometers). In this beautiful town, you and your partner can stop by Ventfort Hall Mansion and Gilded Age Museum. The beauty of the building itself can take your breath away. You can take a self-guided tour that is available between 10am and 3pm. If you like to get spooky, taking a ghost tour of Ventfort Hall is highly recommended. The ghost tours are only available on certain dates, so be sure to check out the official website.
Another romantic thing to do in Lenox is have a leisurely stroll on the groomed trails of Kennedy Park. Here, you can admire beautiful views of the mountain and hardwood forest.
The Yankee, Trademark Collection by Wyndham
Address: 461 Pittsfield Road
14.02 km (8.8 mi) from Norman Rockwell Museum
The Ponds at Foxhollow
Address: 3 Foxhollow Drive
6.22 km (3.9 mi) from Norman Rockwell Museum
Lenox, Massachusetts, United States
8.54 km (5.4 mi) from Norman Rockwell MuseumSuperhost
Accommodates: 4
Top guest reviews
Host:
jared was a responsive hostjared was so responsive to my questions and was around when i arrivedcheck in was easy and the host was really helpfuljared was a very attentive and kind host and we really enjoyed our stayas always jared was a gracious and attentive hostLocation:
jared's place is super cutegreat location for visiting massmocathe location is absolutely stunning and perfect distance to great berkshires destinationsthis is a great central location base for roaming around the berkshireslocation is so convenient to everything you would care to doCleanliness:
clean & homeyeverything was clean bright and well equippedclean spacious peaceful and tastefully decoratedthe place is beautifully designed and very cleanit was a fantastic place to stay very clean and very spaciousRead more reviewsAmenities & Room:
i loved the kitchen area complete with a modern farmer's sink and smeg fridgefurnishings are very high quality (nothing flimsy) and comfortable as wellperfect for a couple lots of room to spread out
2. Stockbridge (from USD 4679)
Delicious dining options, though some find the restaurant a bit outdated for fine dining.
Reasonable rates with occasional increases, especially in summertime Berkshires.
Conveniently situated in the heart of Stockbridge, close to Tanglewood and local attractions.
Charming historic ambience, antique elevator, cozy porches, and a warm outdoor pool.
Located around 8.5 miles (13.68 kilometers) away from Berkshires, Stockbridge can be reached within a quick 15-minute drive. It is a beautiful town perfect for a romantic time with your significant other.
Couples may start their day in the town by visiting Berkshire Botanical Garden. The contemplative Pond Garden and Foster Rock Garden are among visitors’ favorites. The garden also comes with art exhibits. You can enter The Anna and Frederick Henry Leonhardt Galleries for free, as the ticket is already included with the Garden admission. Here, you can indulge in an artsy time as you marvel at pieces of artwork from both regional and international artists. It is also worth stopping by Naumkeag. Be captivated by the beauty of the mansion’s Gilded Age style and charming gardens.
The Red Lion Inn
Address: 30 Main Street
2.08 km (1.3 mi) from Norman Rockwell Museum
Stockbridge, Massachusetts, United States
1.82 km (1.2 mi) from Norman Rockwell MuseumAccommodates: 12
Top guest reviews
Host:
the hosts are exceptional and very responsivegreat and hospitable hostsgeorge and caitlin were wonderful hostsbeautiful home with accommodating hostsgeorge is a fantastic hostLocation:
the location is convenient to shopping and great restaurantsabsolutely beautiful house in a great locationwalking distance to shops and restaurants near lots of berkshire attractions; yet set back overlooking river and hillsthe location is perfect walk to twin and 10 mins to gb or lenoxwhat an amazing location for a large group to get together for a vacationCleanliness:
the house was just as we expected--large clean and cozythe rooms were very clean and there was so much space to spread outRead more reviewsAmenities & Room:
the dining room has the largest and most stunning table i’ve ever seeneach room of the house is filled with fun character giving the ultimate berkshire experiencetaggart house is a wonderful space it is luxurious and comfortable
Stockbridge, Massachusetts, United States
1.01 km (0.7 mi) from Norman Rockwell MuseumAccommodates: 6
Top guest reviews
Host:
the best hospitality we've ever had from an airbnb hostgreat host and great placethe owner did care to make things righthost dan was the bestdan was a very gracious hostLocation:
great skiing close bystockbridge is a super cute town and very close byit's location is perfectly central to anyplace we wanted to goclose to hikes skiing and museums we had a fantastic time exploring the surrounding areastockbridge (the location of this home in particular) is perfectCleanliness:
this place is huge and very cleanthe house was very clean and he is very accommodating and attentive to your needsthe house was so cozy completely renovated perfectly clean and just like the photoswe accepted his gracious offer and were delighted to find a clean cozy beautifully-appointed house upon arrivalRead more reviewsAmenities & Room:
outside there was a lovely deck with an umbrella table swing grill and lounge chairsvery nice spacious and comfortable place in the berkshires recently remodeled with great amenitiesthis is a wonderful light- filled comfortable and well stocked home in a beautiful setting
3. Lee (from USD 842)
Tasty Indian dinner in on-site restaurant, good variety of continental breakfast items.
Reasonable rates, especially for lakefront location.
Conveniently located near Lenox and Stockbridge, beautiful lake views, close to outlet.
On-site Indian restaurant, daily room service, EV charging in parking lot.
The distance from Berkshires to Lee is about a 10-minute drive as it covers a distance of 6 miles. (9.66 kilometers). For this reason, you can still visit Lee easily with your other half.
October Mountain State Forest is an excellent place to visit if you both are adventurers. The trails are suitable for hikers of any level. You can go early during sunrise or if you want to catch the sunset, you can come later. While in Lee, you may also want to stop by Lee Premium Outlets. Get as stylish as you can be with collections from Tommy Hilfiger, Kate Spade and Coach, among others.
The Black Swan Lee - Lenox, Ascend Hotel Collection
Address: 435 Laurel St
7.28 km (4.6 mi) from Norman Rockwell Museum
Lakehouse Inn
Address: 615 Laurel St.
7.38 km (4.6 mi) from Norman Rockwell Museum
Tyringham, Massachusetts, United States
10.65 km (6.7 mi) from Norman Rockwell MuseumAccommodates: 4
Top guest reviews
Host:
the hosts are friendly and nicethe host was excellent quick communicationcheck in was so easy amd the hosts are great people and super helpfulhe was very friendly and accommodatingvery responsive when we needed a little helpLocation:
another bonus is that it's close to town restaurants a grocery store and the highwayi loved this place and josh and shaun were great we will definitely visit againa charming place to stay in the berkshiresthe property is unique beautiful and quietwhat a wonderful placeCleanliness:
charm and character comfort and cleanlinessthe unit was impeccably clean and decorated beautifullyamazing stay absolutely beautiful so clean and quietit was clean comfy cozy had plentiful amenitiesit was minimal and very clean and an easy experienceRead more reviewsAmenities & Room:
the gardens are superb and the beds couches and chairs were super comfyfully equipped kitchen generous newish bathroom and comfortable beds/beddingwe had an amazing stay at the gingerbread house tower it was adorable very thoughtfully decorated and super cozyspacious comfortable living room and nice dining area
You might be interested in these Airbnbs!
4. North Adams (from USD 676)
Several nearby dining options, although the hotel's own restaurant needs improvement.
Reasonable pricing for spacious, clean rooms with mountain views.
Close to Main Street, city hall, and walking distance to restaurants, art museum, and stores.
Convenient location near MASSMoCA, free parking, and modern lobby with coffee service.
Are you ready to embark on the most romantic journey? Travel from Berkshires to North Adams. With just about an hour’s drive, you can explore the beautiful city of North Adams with the most important person in your life.
Take a walk at Natural Bridge State Park and discover an iconic arch along with a natural bridge and a white marble dam. Couples also have an opportunity to explore contemporary art and enjoy performing arts at MASS MoCA. Long-term exhibitions at the museum include Jenny Holzer Benches and Joe Manning: Look at North Adams.
Hotel Downstreet, an Ascend Collection Hotel
Address: 40 Main Street
49.23 km (30.6 mi) from Norman Rockwell Museum
The Porches Inn at Mass MoCA
Address: 231 River Street.
49.54 km (30.8 mi) from Norman Rockwell Museum
North Adams, Massachusetts, United States
50.08 km (31.2 mi) from Norman Rockwell MuseumAccommodates: 6
Top guest reviews
Host:
shana is an amazing host and offers immediate responses and thoughtful touches throughout our stayshana is very responsive and a great hostshana was very thoughtful and responsiveshana was very responsive and pleasantshana was the ideal host and we can't wait to come back to visitLocation:
easy walk to massmocagreat location great spaceswhat a great vacation spot such a great location close to town close to mass moca near to groceriesthis is a great place in a great locationyou could walk into town right near main street with cute shops although some still closedCleanliness:
clean and comfortablegreat communication; beautiful very stylish sparkling clean with every amenitylovely place clean quiet nicely-appointedbeautifully decorated house spotlessly clean very comfortablea clean and cozy homeRead more reviewsAmenities & Room:
the beds and pillows are super comfortable and there's a view of mtthe house is very welcoming with an open kitchen and fun double staircase
5. Pittsfield (from USD 85)
It takes less than 30 minutes to reach Pittsfield from Berkshires. If you are a nature lover, you might want to check out Pittsfield State Forest. It is a serene and popular destination for horseback riding and mountain biking, among other outdoor activities.
For a more indulgent experience with your beloved partner, you can consider heading to The Berkshire Museum. Here, you can gain insights into many things, including natural history and science. Two popular exhibitions at the museum are Animals of the World in Miniature and the Aquarium and Reptile Room.
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Address: 1 West Street
19.0 km (11.9 mi) from Norman Rockwell Museum
Hilton Garden Inn Lenox Pittsfield
Address: 1032 South Street
14.55 km (9.1 mi) from Norman Rockwell Museum
Pittsfield, Massachusetts, United States
19.95 km (12.4 mi) from Norman Rockwell MuseumAccommodates: 2
Top guest reviews
Host:
duane and sheila are also wonderful hostsduane and sheila were great hosts and were wonderful to chat withduane and sheila were great hostsduane and sheila are great hoststhe hosts are accessible if needed and were willing to help as neededLocation:
close to many restaurants (walking distance) as well as centrally located for area attractions and day tripseasy walk to good places to eat in pittsfieldwe had a lovely stay and would absolutely choose their place againperfectly renovated flat in the rear of a house very closed to the main streeta great place to stayCleanliness:
nice and cleanthe apartment was clean quiet and comfortablecomfortable and clean place with everything you needan extremely clean and quiet space for relaxationsqueaky clean newly renovated space lots of roomRead more reviewsAmenities & Room:
it was cozy and a minutes walk to great coffee and breakfastour stay at duane’s place was great the apartment was a perfect size for two people
Enjoy an intimate vacation with your partner in Berkshires
As you can see, Berkshires is a great place for a romantic getaway. The nice thing is that while you are visiting all the above romantic destinations, there are plenty of accommodation options that you can choose from. So, what are you waiting for? It is time to start planning an itinerary and book your favorite places to stay.
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