Title: TOP Romantic Hotels in Great Barrington, MA for 2025 - Great Barrington Romantic Getaways | Expedia.co.uk [Great Barrington Travel Guide](https://expedia.co.uk/Great-Barrington.dx110336)[Hotels in Great Barrington](https://expedia.co.uk/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)[Holiday Rentals in Great Barrington](https://expedia.co.uk/Great-Barrington-Holiday-Rentals.d110336.Travel-Guide-HolidayRentals)[Flights to Great Barrington](https://expedia.co.uk/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights)[Great Barrington Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Great-Barrington.d110336.Car-Hire-Guide)[Great Barrington Holidays](https://expedia.co.uk/Great-Barrington.d110336.Holidays-City-Breaks) ![Great Barrington which includes cbd](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105630-Great-Barrington.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Great Barrington, MA ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Great Barrington Romantic Hotels Tonight [17 Sept - 18 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=110336&startDate=2025-09-17&endDate=2025-09-18&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Sept - 19 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=110336&startDate=2025-09-18&endDate=2025-09-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Sept - 21 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=110336&startDate=2025-09-19&endDate=2025-09-21&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=110336&startDate=2025-09-26&endDate=2025-09-28&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Great Barrington Romantic Hotels ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (722) "We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise " £104 includes taxes & fees 18 Sept - 19 Sept [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (877) "Our stay was very pleasant " £89 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1004) "Good location, lovely grounds, we enjoyed the pool" £97 includes taxes & fees 1 Oct - 2 Oct [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/6d6c1dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, garden views ](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/720e4e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually furnished, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/3c75b29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/985aaf3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gedney Farm Great Barrington 9.2/10 Wonderful (129) "Great property" [](https://www.expedia.co.uk/Great-Barrington-Hotels-Gedney-Farm.h41178000.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Street view](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/bd69c93a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Ground Floor (Main Building) | Premium bedding, in-room safe, desk, soundproofing](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/db6c98da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Lakeside | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/6575d812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Interlaken Inn & Resort Lakeville 8.2/10 Very good (264) "The staff is courteous and accommodating especially the restaurant staff." £189 includes taxes & fees 21 Sept - 22 Sept [](https://www.expedia.co.uk/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1004) "great place have stayed several times, and hope to return." £192 includes taxes & fees 8 Oct - 9 Oct [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/4e933c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9becd207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (259) "Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. " £168 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/7aa060b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Birchwood Suite | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ded30af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Deluxe King | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ed603c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/65e7ad44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dewey Lenox 8.6/10 Excellent (324) "Great spot. Lots of history. " £149 includes taxes & fees 24 Sept - 25 Sept [](https://www.expedia.co.uk/Lenox-Hotels-The-Dewey.h5202927.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed (Dewey Carriage House Inn) | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/468cf971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/f4d43d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Constance by the Lenox Collection Lenox 8.6/10 Excellent (543) "Great place , love it, will return" £117 includes taxes & fees 22 Sept - 23 Sept [](https://www.expedia.co.uk/Lenox-Hotels-Rookwood-Inn.h4945461.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/17dab433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/3ff5efd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/bc78d43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1200000/1197600/1197581/5fa6f6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whistler's Inn Bed & Breakfast Lenox 7.8/10 Good (492) "This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires." £119 includes taxes & fees 18 Sept - 19 Sept [](https://www.expedia.co.uk/Lenox-Hotels-Whistlers-Inn-Bed-Breakfast.h1197581.Hotel-Information) 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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-10-01&endDate=2025-10-02®ionId=110336&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## 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](https://www.expedia.co.uk/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) - **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](https://www.expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) - **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](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) - **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](https://www.expedia.co.uk/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) - **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 ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "great place have stayed several times, and hope to return." [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![The Old Inn On The Green](//images.trvl-media.com/lodging/10000000/9720000/9716100/9716050/90de0046_y.jpg) ### The Old Inn On The Green 10/10 Excellent "Wonderful 19th century inn! We had a spacious corner room with pullout sofa. We enjoyed sitting out on the beautiful balcony. Comfortable, relaxing, quiet stay. As long as you are not expecting a modern, chain-brand property, and have a car, you will enjoy this place! Note, The Old Inn is almost 2 miles from the delicious breakfast spot and about a 16 minute drive to Great Barrington, which is the closest town. There is no lobby or front desk (or tv or coffee maker, etc in room) as one would find in a typical hotel. So if you are looking to wake up and grab a coffee in the lobby or walk across the street to a coffee shop, you’ll need to rethink your game plan. That said, this was a fabulous, relaxing stay in the countryside. Really enjoyed. " [](https://expedia.co.uk/Great-Barrington-Hotels-The-Old-Inn-On-The-Green.h9716050.Hotel-Information) ## 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. 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