TOP 20 Best Vacation getaway in Lenox, Massachusetts

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.

Canyon Ranch Lenox is a renowned institution located at 165 Kemble Street in Lenox, Massachusetts, United States. This institution offers a unique combination of health, lodging, and spa services for guests looking to improve their overall well-being. One of the special offers at Canyon Ranch Lenox is the Best Friends Bonus Offer, where guests can save on double occupancy and receive extra services. The institution also hosts events such as The Canyon Ranch Weight Loss Program, designed to help guests achieve long-term weight loss goals.

Lenox Town Beach is a charming park located at U.S. 20 in Lee, Massachusetts, United States. This beautiful beach offers a serene escape for visitors looking to relax and unwind in a picturesque setting. With its sandy shores and crystal-clear waters, Lenox Town Beach is the perfect spot for swimming, sunbathing, and enjoying the great outdoors. Whether you're looking to spend a leisurely day by the water or enjoy a picnic with family and friends, this park provides a peaceful and idyllic setting for all. Come visit Lenox Town Beach and experience the natural beauty and tranquility of this hidden gem in Lee, Massachusetts.

Howard Johnson by Wyndham Lenox is a charming lodging facility located at 462 Pittsfield Road in Lenox, Massachusetts. Situated in the beautiful Berkshires region, this hotel offers comfortable and affordable accommodations for travelers looking to explore the area. Guests can enjoy spacious rooms, complimentary breakfast, free Wi-Fi, and a seasonal outdoor pool. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Howard Johnson by Wyndham Lenox is the perfect choice for a relaxing getaway in Massachusetts.

Welcome to The Constance, The Whitlock, & The Dewey by The Lenox Collection, your premier lodging destination nestled in the heart of Lenox, Massachusetts. Located at 11 Old Stockbridge Road, our exquisite collection of inns offers a unique blend of historical charm, modern comfort, and serene surroundings, perfect for every traveler seeking a memorable escape in the Berkshires. The Dewey: Discover our most intimate inn, featuring 12 uniquely designed guestrooms that capture the essence of historical elegance amidst peaceful natural surroundings. Situated just north of downtown Lenox, The Dewey offers a harmonious balance of accessibility to local dining and shopping, and the tranquility of Pleasant Valley. Each room, surrounded by lush treetops, invites you to relax and rejuvenate in a beautifully preserved historic setting. Ideal for the discerning traveler, The Dewey promises a serene retreat.

Knights Inn Lenox is a charming lodging establishment located at 474 Pittsfield Road in Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and excellent service to ensure a pleasant stay for guests. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's attractions, including Tanglewood, Norman Rockwell Museum, and the beautiful landscapes of the region. With its affordable rates and welcoming atmosphere, Knights Inn Lenox is the perfect choice for travelers looking for a relaxing retreat in western Massachusetts.

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.

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.

The Mount, Edith Wharton's Home, located at 2 Plunkett Street, Lenox, MA 01240, is a captivating museum and tourist attraction dedicated to the life and legacy of the renowned American author, Edith Wharton. This beautifully preserved estate offers visitors a unique glimpse into the Gilded Age, showcasing the architectural and horticultural designs that Wharton herself meticulously planned. The Mount features a stunning main house, lush gardens, and picturesque grounds, all of which reflect Wharton's sophisticated taste and literary genius. Guests can explore the elegant rooms filled with period furnishings, admire the extensive library, and gain insight into Wharton's life through informative exhibits and guided tours. The estate also hosts a variety of cultural events, including literary discussions, garden tours, and art exhibitions, making it a vibrant cultural hub in the Berkshires. Whether you're a literature enthusiast, history buff, or simply looking for a serene and inspiring setting, The Mount offers a rich and engaging experience for all visitors.

Stonover Farm is a charming lodging institution located at 169 Under Mountain Road in Lenox, Massachusetts, United States. Surrounded by picturesque countryside, this tranquil farm offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The property features beautifully appointed rooms, a cozy fireplace, and stunning views of the rolling hills. Guests can enjoy a relaxing stay in this idyllic setting, with opportunities for hiking, biking, and exploring the nearby attractions. Whether you're seeking a romantic getaway or a peaceful weekend retreat, Stonover Farm provides a warm and welcoming atmosphere for a memorable stay.

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.

Miraval Berkshires Resort & Spa is a luxurious wellness retreat nestled in the picturesque town of Lenox, Massachusetts. Situated at 55 Lee Road, this institution offers a serene escape for those seeking relaxation and rejuvenation. With a focus on health and well-being, guests can indulge in a variety of spa treatments, fitness classes, and healthy dining options. The resort also provides luxurious lodging accommodations, including spacious rooms and suites with modern amenities. Whether you're looking to unwind with a massage, practice yoga in a peaceful setting, or simply enjoy the tranquil surroundings, Miraval Berkshires Resort & Spa is the perfect destination for a restorative getaway.

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.

Eastover Estate & Eco-Village is a serene retreat nestled in the heart of Lenox, Massachusetts. This unique institution offers a perfect blend of health, lodging, and spa services, making it an ideal destination for those seeking relaxation and rejuvenation. Situated at 430 East Street, Eastover Estate & Eco-Village provides a tranquil environment surrounded by nature, where guests can unwind and escape the hustle and bustle of everyday life. Whether you are looking to pamper yourself with a spa treatment, practice yoga in a peaceful setting, or simply enjoy a restful stay in luxurious accommodations, Eastover Estate & Eco-Village has something for everyone. Come experience the tranquility and wellness that this institution has to offer.

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.

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.

Sloane's Pool is a luxurious and exclusive institution located in the picturesque town of Lenox, Massachusetts, United States. Nestled in the heart of the Berkshires, this elegant establishment offers a serene and tranquil setting for guests to relax and unwind. With a stunning outdoor pool surrounded by lush gardens and breathtaking views of the mountains, Sloane's Pool is the perfect escape for those seeking a peaceful retreat. Whether you're looking to swim laps, soak up the sun, or simply enjoy the peaceful ambiance, Sloane's Pool is the ultimate destination for relaxation and rejuvenation.

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.

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.