TOP 30 Best Romantic getaways in berkshires in Lenox, Massachusetts

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

Courtyard by Marriott Lenox Berkshires is a charming lodging option located at 70 Pittsfield Road in Lenox, Massachusetts, United States. Situated in the beautiful Berkshires region, this hotel offers modern amenities and comfortable accommodations for guests looking to explore the area's cultural attractions, outdoor activities, and scenic landscapes. With spacious rooms, a fitness center, indoor pool, and on-site dining options, Courtyard by Marriott Lenox Berkshires is the perfect choice for travelers seeking a relaxing and convenient stay in this picturesque New England town.

The Black Swan Lee - Lenox, Ascend Hotel Collection is a charming lodging institution located at 435 Laurel Street in Lee, Massachusetts, United States. This unique hotel offers a cozy and inviting atmosphere for guests to relax and unwind during their stay. With comfortable accommodations and top-notch amenities, The Black Swan Lee is the perfect choice for travelers looking for a memorable experience in the heart of the Berkshires. Whether you are visiting for business or pleasure, this hotel is sure to exceed your expectations with its exceptional service and convenient location. Book your stay at The Black Swan Lee - Lenox, Ascend Hotel Collection for a truly unforgettable experience.

Life House, Berkshires is a charming lodging located at 194 Pittsfield Road in Lenox, Massachusetts. Nestled in the picturesque Berkshires region, this institution offers a peaceful and serene retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a welcoming atmosphere for visitors to relax and unwind. With its convenient location and warm hospitality, Life House, Berkshires is the perfect destination for a memorable getaway in the heart of the Berkshires.

The Chesapeake Inn of Lenox is a charming lodging establishment located at 210 West Street in the picturesque town of Lenox, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. With its convenient location near historic sites, cultural attractions, and outdoor activities, the Chesapeake Inn of Lenox is the perfect destination for a peaceful getaway or romantic retreat. Experience the beauty and hospitality of Lenox at this charming inn.

Berkshire Inns is a charming lodging institution located at 461 Pittsfield Road in Lenox, Massachusetts, United States. Offering comfortable and cozy accommodations, Berkshire Inns provides a peaceful retreat for guests looking to explore the beautiful Berkshires region. With its convenient location and welcoming atmosphere, Berkshire Inns is the perfect choice for travelers seeking a relaxing stay in the heart of New England.

1-A Lenox Bed & Breakfast is a charming lodging located at 31 Delafield Drive in Lenox, Massachusetts. This cozy bed and breakfast offers a comfortable and welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. The beautifully decorated rooms feature modern amenities and luxurious touches to ensure a memorable stay. Guests can enjoy a delicious homemade breakfast each morning and take advantage of the convenient location near local attractions, shops, and restaurants. Whether you are visiting for a romantic getaway or a weekend escape, 1-A Lenox Bed & Breakfast is the perfect choice for your stay in Lenox.

33 Main offers a luxurious lodging experience curated by renowned designer Annie Selke. Located in the charming town of Lenox, Massachusetts, this upscale accommodation combines modern amenities with classic New England charm. Each room is elegantly decorated with Selke's signature style, creating a cozy and inviting atmosphere for guests to relax and unwind. With its prime location on Main Street, guests can easily explore the local shops, restaurants, and cultural attractions that Lenox has to offer. Whether you're visiting for a romantic getaway or a weekend retreat, 33 Main promises a memorable and indulgent stay in the heart of the Berkshires.

Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.

Welcome to Brook Farm Inn, a charming lodging establishment located at 15 Hawthorne Street in Lenox, Massachusetts. Our Victorian Inn offers 15 guest rooms, including a carriage house with three luxury accommodations, perfect for a relaxing getaway in the beautiful Berkshires. Surrounded by trees and award-winning gardens, our inn provides a serene and secluded atmosphere, while still being just a short walk from historic Lenox village. Built in 1882 and furnished with antiques, our elegant inn features a library filled with poetry, history, and literature, where guests can enjoy the soothing sounds of classical music. Each room at Brook Farm Inn includes a full plated breakfast, providing a perfect start to the day before exploring all that the Berkshires have to offer. From skiing and hiking to theater and antiquing, there is something for everyone to enjoy in the area.

The Cornell Inn is a charming lodging establishment located at 203 Main Street in Lenox, Massachusetts, United States. This historic inn offers cozy accommodations, friendly service, and a convenient location in the heart of the Berkshires. Guests can relax in comfortable rooms, enjoy a delicious breakfast, and explore the nearby shops, restaurants, and attractions. Whether you're visiting for a romantic getaway, a family vacation, or a business trip, the Cornell Inn is the perfect place to stay in Lenox.

Wheatleigh is a luxurious lodging institution located on Hawthorne Road in Lenox, Massachusetts, United States. This grand estate offers a unique and elegant experience for guests looking to immerse themselves in opulence and sophistication. With its stunning architecture, lush gardens, and impeccable service, Wheatleigh provides a truly unforgettable stay for those seeking a refined retreat in the heart of the Berkshires. Whether you are looking for a romantic getaway, a peaceful escape, or a lavish event venue, Wheatleigh promises to exceed your expectations and create lasting memories.

The Constance is a charming lodging located at 11 Old Stockbridge Road in Lenox, Massachusetts. This historic institution offers cozy accommodations in a picturesque setting, perfect for a relaxing getaway in the heart of the Berkshires. Guests can enjoy comfortable rooms, beautiful gardens, and personalized service during their stay. Whether you're looking for a weekend retreat or a longer vacation, The Constance is the perfect choice for a memorable experience in this idyllic New England town.

Welcome to Stevens Glen Trail Head, a serene and picturesque park located in the heart of the Berkshires at Lenox Road, West Stockbridge, Massachusetts. Nestled in the lush greenery of Richmond, MA, our park offers a tranquil escape for nature lovers and outdoor enthusiasts. Stevens Glen Trail Head is renowned for its breathtaking landscapes, featuring well-maintained trails that wind through dense forests, alongside babbling brooks, and past stunning waterfalls. Whether you're a seasoned hiker or just looking for a peaceful walk in nature, our trails cater to all skill levels, providing a perfect opportunity to reconnect with the great outdoors.

Blantyre is a luxurious lodging institution located at 16 Blantyre Road in the picturesque town of Lenox, Massachusetts, United States. This historic property offers elegant accommodations, impeccable service, and stunning views of the surrounding Berkshire Mountains. Guests can enjoy fine dining, relaxing spa treatments, and a variety of outdoor activities on the expansive grounds. Blantyre is the perfect destination for a romantic getaway, a special occasion, or a relaxing retreat in a beautiful New England setting.

Yankee Inn, Trademark Collection by Wyndham is a charming lodging establishment located at 461 Pittsfield Road in Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and top-notch amenities, making it the perfect place to relax and unwind during your stay in the beautiful Berkshires. With its convenient location and warm hospitality, Yankee Inn is the ideal choice for travelers looking for a memorable and enjoyable experience in Lenox.

Whistler's Inn is a charming lodging establishment located at 5 Greenwood Street in the picturesque town of Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and personalized service to make guests feel right at home. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Whistler's Inn is the perfect choice for travelers looking to experience the beauty and culture of the Berkshires. Whether you're visiting for a romantic getaway or a family vacation, Whistler's Inn provides a peaceful retreat in the heart of Lenox.

The Ponds at Foxhollow is a secluded resort located in the heart of the Berkshire Mountains at 3 Fox Hollow Drive, Lenox, Massachusetts. The resort offers one and two bedroom condominiums for timesharing or rental purposes, each with a master bedroom, fully equipped kitchen, living area with a double sleeper sofa, and a deck overlooking a picturesque pond. The property spans 223 acres, perfect for hiking in the warmer months and cross country skiing in the winter. The resort also offers outdoor activity equipment and canoes for guests to use. With breathtaking mountain views and a variety of recreational and cultural activities nearby, The Ponds at Foxhollow is the perfect destination for a relaxing getaway. Please note that the hot tub is temporarily out of service, but a new one is on the way.

Located at 10 Richmond Mountain Road in Lenox, Massachusetts, the Apple Tree Inn is a charming lodging option that serves as the perfect retreat for those looking to nurture their creativity. Surrounded by the natural beauty of the Berkshires, this institution offers a peaceful escape from the ordinary where guests can unlock new ideas and inspiration. The inn features a picturesque 1885 Victorian main house with 13 rooms that blend historic charm with modern amenities such as Frette linens. Additionally, there is a rustic Lodge with 21 rooms that provide a cozy and tranquil setting overlooking the lush green forests and rolling hills of the Berkshires.

Winthrop Estate is a luxurious lodging institution located at 101 Yokun Avenue in the charming town of Lenox, Massachusetts, United States. Nestled in the heart of the Berkshires, this historic estate offers guests a unique and unforgettable experience. The elegant accommodations, stunning gardens, and impeccable service make Winthrop Estate the perfect destination for a romantic getaway, family vacation, or special event. With its rich history and picturesque surroundings, Winthrop Estate truly embodies the essence of New England charm and hospitality.

Welcome to Seranak Cottage, a charming retreat nestled in the heart of Lenox, Massachusetts. Located at the picturesque address of Lenox, Massachusetts 01240, our cottage offers a serene escape for those seeking tranquility and comfort in the beautiful Berkshires. Seranak Cottage is steeped in history and surrounded by natural beauty, providing an ideal setting for relaxation and rejuvenation. Whether you're planning a romantic getaway, a family vacation, or a solo retreat, our cottage promises a cozy and inviting atmosphere.

Welcome to MeadowView, your serene escape nestled in the heart of the Berkshires at 112 Lee Road, Lenox, Massachusetts. Our charming establishment offers a peaceful retreat surrounded by the natural beauty of New England. Whether you're seeking a weekend getaway, a family vacation, or a venue for a special event, MeadowView provides a perfect blend of comfort and elegance. At MeadowView, we pride ourselves on delivering exceptional hospitality and personalized service. Our cozy accommodations are thoughtfully designed to ensure a relaxing stay, with amenities that cater to both leisure and business travelers. Enjoy a stroll through our beautifully landscaped gardens, unwind on our spacious terrace, or explore the nearby attractions that make Lenox a cultural and recreational hub.

Wagon Wheel Inn is a charming lodging located at 484 Pittsfield Road in Lenox, Massachusetts. Nestled in the heart of the beautiful Berkshire Mountains, this cozy inn offers comfortable accommodations and a warm, welcoming atmosphere. Guests can relax in well-appointed rooms, enjoy a delicious complimentary breakfast, and take advantage of convenient amenities such as free Wi-Fi and onsite parking. Whether you're visiting for a weekend getaway or a longer stay, Wagon Wheel Inn is the perfect home base for exploring all that Lenox has to offer.

Located in the charming town of Lenox, Massachusetts, the Eastgate Inn Bed & Breakfast offers a cozy and welcoming atmosphere for travelers looking for a peaceful retreat. Situated at 207 West Street, this quaint lodging establishment provides comfortable accommodations with a personal touch. Guests can enjoy a delicious homemade breakfast each morning before exploring the nearby attractions such as Tanglewood, The Mount, and the shops and restaurants of Lenox. Whether you are visiting for a romantic getaway or a relaxing vacation, the Eastgate Inn Bed & Breakfast is the perfect place to stay in the heart of the Berkshires.

Walker House is a historic institution located at 64 Walker Street in the charming town of Lenox, Massachusetts. This elegant building offers a unique blend of traditional charm and modern amenities, making it the perfect destination for visitors looking to experience the beauty of the Berkshires. With its picturesque surroundings and convenient location, Walker House is the ideal spot for a relaxing getaway or a special event. Immerse yourself in the rich history and warm hospitality of this iconic institution during your stay in Lenox.

26 Church Street is a charming lodging institution located in the heart of Lenox, Massachusetts. Situated at the address 26 Church Street, this cozy establishment offers a warm and inviting atmosphere for guests looking to experience the beauty of the Berkshires. With comfortable accommodations and a convenient location near local attractions, 26 Church Street is the perfect choice for a relaxing getaway in this picturesque New England town. Whether you're exploring the nearby shops and restaurants or simply unwinding in your well-appointed room, you'll feel right at home at this lovely inn.

Sage & Sparrow at Wheatleigh Hotel is an elegant dining establishment located at 11 Hawthorne Road in Lenox, Massachusetts. This renowned restaurant offers a sophisticated and intimate atmosphere, perfect for special occasions or romantic dinners. With a menu that features locally sourced ingredients and expertly crafted dishes, guests can indulge in a culinary experience that is both refined and innovative. Whether you are looking for a gourmet meal or a relaxing evening with drinks and appetizers, Sage & Sparrow at Wheatleigh Hotel is sure to impress with its impeccable service and exquisite cuisine.

Welcome to Great Barrington Resort House, your serene getaway nestled in the picturesque landscapes of Lenox, Massachusetts. Located at the heart of the Berkshires, our resort offers a perfect blend of luxury, comfort, and natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled vacation, our resort is the ideal destination. At Great Barrington Resort House, we pride ourselves on providing exceptional hospitality and personalized service. Our elegantly designed rooms and suites offer breathtaking views and modern amenities to ensure a relaxing stay. Enjoy gourmet dining at our on-site restaurant, unwind at our spa, or take a dip in our heated pool.