Top 5 Romantic Getaways in Berkshires, MA

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Couples looking to indulge in a romantic getaway should look no further than Berkshires, Massachusetts. Whether you come during weekdays or weekends, spring, summer, or any other season, you’ll have plenty of options. Mount Greylock State Reservation is a popular romantic attraction here. Camping, snowmobiling, or other activities can allow you to reconnect with nature. For religious couples, the nearby National Shrine of The Divine Mercy offers healing mass services and a peaceful atmosphere. In Berkshires, you won’t be short of romantic destinations. Read on to learn more about the best romantic getaways in Berkshires!

1 Lenox

Image of Lenox

Are you ready for an adventure? In just 17 minutes by car, you can travel from the Berkshires to the charming town of Lenox, covering a distance of 10.3 miles (16.58 kilometers). Once in Lenox, prepare to be amazed by the stunning Ventfort Hall Mansion and Gilded Age Museum. The architectural beauty will leave you breathless. Don’t miss the opportunity to take a self-guided tour between 10am and 3pm. If you’re feeling brave, I highly recommend the ghost tour of Ventfort Hall, but make sure to check the official website for available dates. For a romantic experience, take a leisurely stroll through the groomed trails of Kennedy Park. The picturesque views of the mountains and hardwood forest are simply enchanting.

Additional Information
  • Name: Lenox
  • Rating: 3.0/5
  • Address: 3 Foxhollow Drive 6.22 km from Norman Rockwell Museum
  • Services:
    • Parking
    • Tennis court
    • Sauna
    • Fitness centre
    • 3 Golf course (within km)
    • Garden
    • Terrace
    • Non-smoking rooms
    • Parking
    • Meeting/banquet facilities
    • 24 -hour front desk
    • Fitness centre
    • Non-smoking rooms
    • Business centre
    • Skiing
    • Free parking
    • Entire guesthouse
    • 2 Beds
    • 4 Guests
    • 1 Bedroom
    • 1 Bathroom
  • Reviews:
    • Amenities & Room | i loved the kitchen area complete with a modern farmer's sink and smeg fridge
    • Cleanliness | clean & homey
    • Host | jared was a responsive host
    • Location | jared's place is super cute

2 Stockbridge

Image of Stockbridge

Just 15 minutes away from Berkshires lies Stockbridge, the perfect destination for a romantic getaway. Couples can begin their day at the Berkshire Botanical Garden with the Pond Garden and Foster Rock Garden, two favorites among visitors. Admission to the Anna and Frederick Henry Leonhardt Galleries is free with the Garden ticket, where visitors can view regional and international art pieces. Naumkeag is also a must-see, with its Gilded Age style mansion and stunning gardens.

Additional Information
  • Name: Stockbridge
  • Rating: 4.0/5
  • Address: Stockbridge
  • Services:
    • Parking
    • Restaurant
    • Pets allowed
    • Meeting/banquet facilities
    • Bar
    • 24 -hour front desk
    • Fitness centre
    • 3 Golf course (within km)
    • ENTIRE HOME
    • 4 Beds
    • 6 Guests
    • 3 Bedrooms
    • 2 Bathrooms
    • Entire villa
    • 8 Beds
    • 12 Guests
    • 6 Bedrooms
    • 7 Bathrooms
  • Reviews:
    • Amenities & Room | outside there was a lovely deck with an umbrella table swing grill and lounge chairs
    • Cleanliness | this place is huge and very clean
    • Host | the best hospitality we've ever had from an airbnb host
    • Location | great skiing close by

3 Lee

Image of Lee

If you and your other half are looking for a quick adventure, the Berkshires to Lee is only a 10-minute drive away at 6 miles (9.66 kilometers). October Mountain State Forest is an ideal spot with trails perfect for hikers of any level, whether you choose to go early in the morning to watch the sunrise or later for a beautiful sunset. Don’t forget to check out Lee Premium Outlets and browse through the stylish collections from Tommy Hilfiger, Kate Spade, and Coach.

Additional Information
  • Name: Lee
  • Rating: 3.0/5
  • Address: 615 Laurel Street 7.38 km from Norman Rockwell Museum
  • Services:
    • Parking
    • Bar
    • 3 Golf course (within km)
    • Garden
    • Terrace
    • Non-smoking rooms
    • Fishing
    • Facilities for disabled guests
    • Parking
    • Restaurant
    • Pets allowed
    • Room service
    • Meeting/banquet facilities
    • Bar
    • 24 -hour front desk
    • Fitness centre
    • Treehouse
    • 2 Beds
    • 4 Guests
    • 2 Bedrooms
    • 1 Bathroom
  • Reviews:
    • Amenities & Room | the gardens are superb and the beds couches and chairs were super comfy
    • Cleanliness | charm and character comfort and cleanliness
    • Host | the hosts are friendly and nice
    • Location | another bonus is that it's close to town restaurants a grocery store and the highway

4 North Adams

Image of North Adams

Embark on a romantic journey with the most important person in your life – only an hour’s drive away from Berkshires to North Adams! Spend some quality time together exploring Natural Bridge State Park, where you’ll find a beautiful arch, natural bridge and a white marble dam. Get creative and enjoy contemporary art and performing arts at MASS MoCA. Don’t forget to explore the long-term exhibitions such as Jenny Holzer Benches and Joe Manning’s Look at North Adams!

Additional Information
  • Name: North Adams
  • Rating: 3.0/5
  • Address: 40 Main Street 49.23 km from Norman Rockwell Museum
  • Services:
    • Parking
    • Restaurant
    • Pets allowed
    • 24 -hour front desk
    • Fitness centre
    • Non-smoking rooms
    • Business centre
    • Laundry
    • Parking
    • Pets allowed
    • Room service
    • Meeting/banquet facilities
    • Bar
    • 24 -hour front desk
    • 3 Golf course (within km)
    • Garden
    • ENTIRE HOME
    • 4 Beds
    • 6 Guests
    • 3 Bedrooms
    • 1 Bathrooms
  • Reviews:
    • Amenities & Room | the beds and pillows are super comfortable and there's a view of mt
    • Cleanliness | clean and comfortable
    • Host | shana is an amazing host and offers immediate responses and thoughtful touches throughout our stay
    • Location | easy walk to massmoca

5 Pittsfield

Image of Pittsfield

Pittsfield, located in the Berkshires, is less than a 30-minute journey away. Nature enthusiasts may find Pittsfield State Forest appealing, as it offers a tranquil setting for activities like horseback riding and mountain biking. For a more romantic outing, The Berkshire Museum is worth considering. This museum provides insights into various subjects, such as natural history and science, and features popular exhibitions like Animals of the World in Miniature and the Aquarium and Reptile Room.

Additional Information
  • Name: Pittsfield
  • Rating: 4.0/5
  • Address: 1 West Street 19.0 km from Norman Rockwell Museum
  • Services:
    • Restaurant
    • Pets allowed
    • Meeting/banquet facilities
    • Bar
    • 24 -hour front desk
    • Tennis court
    • Fitness centre
    • 3 Golf course (within km)
    • Parking
    • Restaurant
    • Pets allowed
    • Meeting/banquet facilities
    • 24 -hour front desk
    • Fitness centre
    • Business centre
    • Laundry
    • ENTIRE RENTAL UNIT
    • 1 Bed
    • 2 Guests
    • 1 Bedroom
    • 1 Bathroom
  • Reviews:
    • Amenities & Room | it was cozy and a minutes walk to great coffee and breakfast
    • Cleanliness | nice and clean
    • Host | duane and sheila are also wonderful hosts
    • Location | close to many restaurants (walking distance) as well as centrally located for area attractions and day trips

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