Find Romantic Hotels in Great Barrington, MA

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Our top choices for Great Barrington romantic hotels

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (277 reviews)
"The property is very nice, well stocked amenities. Cozy and warm and perfect for a long weekend getaway. "
United States
Jonathan H.
The price is £156
includes taxes & fees
13 May - 14 May
Berkshire Village Carriage House - Super Private!!

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is £147
includes taxes & fees
13 May - 14 May
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (105 reviews)
"Everything was lovely! The host was welcoming, the cottage was adorable. Amenities were great (fire was on when we got there, warming blankets on the bed). So cozy! Perfect place to snuggle up during the coldest weekend of the year. We'd definitely stay again. "
United States
Jennifer H.
The price is £186
includes taxes & fees
18 May - 19 May
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is £253
includes taxes & fees
13 May - 14 May
rural, serene + sophisticated space

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is £327
includes taxes & fees
17 May - 18 May
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is £1,074
includes taxes & fees
14 May - 15 May
A Country Lodge Straight Out of the Pages of a Great Novel
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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