Find Romantic Hotels in Great Barrington, MA

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Our top choices for Great Barrington romantic hotels

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (135 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is £149
includes taxes & fees
15 Feb - 16 Feb
Gedney Farm

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is £76
includes taxes & fees
22 Feb - 23 Feb
The Yankee, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,005 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is £84
includes taxes & fees
7 Mar - 8 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (855 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is £72
includes taxes & fees
8 Mar - 9 Mar
Berkshires Untold

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is £152
includes taxes & fees
10 Mar - 11 Mar
The Red Lion Inn

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (280 reviews)
"Great"
United States
Jorge
The price is £175
includes taxes & fees
16 Feb - 17 Feb
Interlaken Inn & Resort

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very good, (13 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is £133
includes taxes & fees
11 Feb - 12 Feb
The Millerton Inn

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is £115
includes taxes & fees
11 Feb - 12 Feb
Changing Times Boutique Country Lodging

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is £134
includes taxes & fees
16 Feb - 17 Feb
Blackberry River Inn

The Nest Hudson

The Nest Hudson
3.5 star property
Hudson
9.6 out of 10, Exceptional, (219 reviews)
"Great stay! Great location!"
Canada
Amanda
The Nest Hudson
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.

Find out more about Great Barrington

Great Barrington attractions for couples

Great Barrington, Massachusetts, is a charming town brimming with activities that cater to discerning travellers. Start your day with a visit to the Norman Rockwell Museum, where you can admire an extensive collection of the artist’s work and gain insight into his life. For those who enjoy the great outdoors, a hike up Monument Mountain offers spectacular views of the Berkshires, making it an energising experience for the whole family. Afterward, unwind at Lake Mansfield Park, where you can swim, kayak, or simply relax by the water's edge. Food enthusiasts will delight in dining at the renowned Prairie Whale, known for its farm-to-table menu featuring local ingredients. Lastly, indulge in a little retail therapy at the charming shops along Main Street, where you can discover unique crafts and artisanal goods. For a comfortable stay, consider the picturesque downtown area, which boasts boutique hotels like The Briarcliff Motel. Here, you'll find attentive service and a warm atmosphere that complements your exploration of this delightful town.

Find the best romantic hotels in Great Barrington

For couples seeking a romantic escape in Great Barrington, these charming hotels offer inviting atmospheres and delightful amenities to enhance your stay.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

  • Why it's great for a couples retreat: Ideal for a romantic getaway, the Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires boasts an impressive guest review rating of 9.4. Guests can indulge in a refreshing dip in the indoor pool or enjoy a complimentary breakfast together, setting the stage for a delightful day ahead. The surrounding mountains provide a picturesque backdrop, perfect for intimate hikes or peaceful strolls.
  • Other amenities: Additional amenities include free self-parking, a fitness centre for those who wish to stay active, and a snow tubing location nearby for a touch of adventure. The hotel also features inviting seating areas and a daily housekeeping service, ensuring a comfortable and stress-free stay. With easy access to the area's skiing and hiking opportunities, this hotel truly caters to couples looking to explore the natural beauty of the Berkshires together.
  • Nearby attractions: Housatonic River - 0.5 km, Housatonic River Walk - 2.1 km, Mahaiwe Performing Arts Center - 2.6 km

Holiday Inn Express Hotel & Suites Great Barrington by IHG

  • Why it's great for a couples retreat: The Holiday Inn Express Hotel & Suites offers a charming stay for couples with a review rating of 8.8. Guests can start their day with a complimentary breakfast before exploring the nearby mountains or enjoying a romantic swim in the indoor pool. The inviting atmosphere and thoughtful amenities make it a perfect choice for a romantic getaway.
  • Other amenities: This hotel also features air conditioning for comfort, along with a fitness facility for those wanting to stay active. Guests can enjoy separate living areas with sofa beds, along with suites that offer additional privacy. With easy access to local ski areas and hiking trails, couples can create memorable experiences in the great outdoors.
  • Nearby attractions: Housatonic River - 0.1 km, Housatonic River Walk - 2.9 km, Mahaiwe Performing Arts Center - 3.4 km

Monument Mountain Motel

  • Why it's great for a couples retreat: The Monument Mountain Motel is a charming option for couples seeking a cozy retreat, with a solid review rating of 8.8. Guests can enjoy the tranquility of the motel while being surrounded by nature, making it perfect for romance. The hotel offers daily housekeeping to keep the space comfortable and tidy, ensuring couples can focus on each other.
  • Other amenities: Additional features include free self-parking and air conditioning for a pleasant stay. Each room is equipped with a microwave for late-night snacks or breakfast in bed. The nearby ski areas add an adventurous element to your stay, allowing couples to indulge in winter sports or simply enjoy the stunning views together.
  • Nearby attractions: Housatonic River - 0.3 km, Housatonic River Walk - 2.1 km, Mahaiwe Performing Arts Center - 2.6 km

The Little Lion

  • Why it's great for a couples retreat: The Little Lion is a charming hotel that captures the essence of romance with its budget-friendly offerings and a review rating of 8.6. Guests can revel in the peaceful garden setting, creating an idyllic backdrop for romantic evenings. The hotel features premium bedding for a restful night's sleep and daily housekeeping, allowing couples to focus on each other during their stay.
  • Other amenities: Additional features include free self-parking and air conditioning for comfort. The hotel also offers easy access to nearby ski locations, perfect for adventurous couples. With cozy rooms equipped with microwaves, late-night snacks are just a moment away, making it a perfect choice for a warm and intimate getaway.
  • Nearby attractions: Housatonic River - 2.1 km, Schantz Galleries - 5.2 km

Top Great Barrington Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Great Barrington?
If you and your partner need a romantic holiday, we've got just the ticket. Our guests also love Great Barrington for its hiking, skiing and array of dining options. If you want to explore the area, you might head to Housatonic River Walk, Housatonic River or Mahaiwe Performing Arts Center. If you're interested in staying near a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Great Barrington?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in Great Barrington: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Great Barrington are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Great Barrington?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that Great Barrington has to offer. Couples looking for a little of everything will enjoy Great Barrington for its live music, theatre scene and restaurants. You might consider a visit to Housatonic River Walk, Housatonic River or Mahaiwe Performing Arts Center.
What's the best way to get to Great Barrington and around town during my romantic getaway?
This information about transportation options in Great Barrington might help your romantic trip get off to a smooth start: If you're looking to fly to Great Barrington, the closest major airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city centre. If you'd like to venture out around the area, consider renting a car to explore more sights.

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