TOP 30 Best Relaxing getaway in Pittsfield, 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.

Berkshire Yankee Suites is a charming lodging establishment located at 20 West Housatonic Street in the picturesque city of Pittsfield, Massachusetts. Our suites offer a cozy and comfortable stay for travelers looking to explore the beautiful Berkshire region. Each suite is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. Our convenient location allows guests easy access to local attractions, dining options, and outdoor activities. Whether you are visiting for business or pleasure, Berkshire Yankee Suites is the perfect home away from home in the heart of the Berkshires.

Hotel on North is a charming and sophisticated institution located in the heart of Pittsfield, Massachusetts. Situated at 297 North Street, this unique establishment offers a combination of luxurious lodging, a vibrant bar, and a lively night club all under one roof. Guests can enjoy stylish accommodations, delicious cocktails, and exciting entertainment all in one convenient location. Whether you're looking for a relaxing retreat or a fun night out, Hotel on North has something for everyone. Experience the best of Pittsfield at this one-of-a-kind destination.

Berkshire Mountain Lodge is a charming lodging institution located at 8 Dan Fox Drive in Pittsfield, Massachusetts. Situated in the beautiful Berkshires region, the lodge offers a perfect blend of cultural attractions, historical sites, and natural beauty. Guests can explore nearby attractions such as The Mount, the former estate of American author Edith Wharton, and Tanglewood, the summer home of the Boston Symphony Orchestra. Berkshire Mountain Lodge is a family-friendly vacation destination that offers a variety of amenities and activities for guests of all ages. The resort has received numerous awards, including the RCI Gold Crown Status, Tripadvisor's Travelers' Choice Award, and the Hotels.com Loved by Guests Award, all of which recognize the exceptional service and hospitality provided by the lodge.

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.

Bonnie Brae Campground is a picturesque retreat nestled in the heart of Pittsfield, Massachusetts. Located at 108 Broadway Street, this charming campground offers a peaceful escape for nature lovers and outdoor enthusiasts. With spacious campsites, cozy lodging options, and beautiful park amenities, Bonnie Brae Campground is the perfect destination for a weekend getaway or extended vacation. Whether you prefer hiking through the lush forests, fishing in the nearby lakes, or simply relaxing by the campfire, this campground has something for everyone. Come experience the beauty and tranquility of Bonnie Brae Campground in Pittsfield, Massachusetts.

Located in the picturesque town of Pittsfield, Massachusetts, the Best Western Plus Berkshire Hills Inn & Suites offers comfortable and modern lodging for travelers looking to explore the beautiful Berkshires region. Situated at 1350 West Housatonic Street, this hotel provides guests with a convenient location near popular attractions such as Tanglewood, Hancock Shaker Village, and the Norman Rockwell Museum. The hotel features spacious rooms and suites equipped with amenities such as free Wi-Fi, flat-screen TVs, and mini fridges. Guests can also enjoy a complimentary hot breakfast, a fitness center, and an indoor pool. Whether visiting for business or leisure, the Best Western Plus Berkshire Hills Inn & Suites provides a welcoming and relaxing atmosphere for all guests.

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.

Berkshire Travel Group is a premier travel agency located at 1450 East Street in Pittsfield, Massachusetts, United States. With a team of experienced travel experts, we provide personalized service and tailored travel packages to meet the unique needs of our clients. Whether you're looking to plan a relaxing beach getaway, an adventurous hiking trip, or a luxurious cruise vacation, we are here to help make your travel dreams a reality. Contact us today to start planning your next unforgettable journey with Berkshire Travel Group.

Welcome to Berkshire Knapsackers, your ultimate destination for outdoor adventure and relaxation located at 11 Churchill Street, Pittsfield, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape for nature enthusiasts and families alike. Explore our lush trails, perfect for hiking and bird watching, or enjoy a leisurely picnic amidst the stunning natural beauty. Whether you're seeking a peaceful retreat or an active day out, Berkshire Knapsackers provides a picturesque setting to reconnect with nature. Visit us today and discover the tranquility and charm of our beloved park.

Welcome to Berkshire Mobile Home Park, your serene getaway nestled in the heart of the picturesque Berkshires. Conveniently located at 413 Pittsfield Road in Lenox, Massachusetts, our park offers a peaceful retreat for those seeking a unique lodging experience. Whether you're visiting for a weekend escape or an extended stay, you'll find comfort and convenience in our well-maintained facilities. Berkshire Mobile Home Park is not just an RV park; it's a community. We offer spacious lots with full hookups, ensuring you have everything you need for a comfortable stay. Our park is surrounded by the natural beauty of the Berkshires, providing a perfect backdrop for outdoor enthusiasts and nature lovers. Explore nearby hiking trails, enjoy the vibrant local culture, or simply relax and take in the tranquil surroundings.

Welcome to Allen Heights Park, your serene escape nestled in the heart of Pittsfield, Massachusetts. Located at 150 Windsor Avenue, our charming park offers a perfect blend of natural beauty and recreational facilities, making it an ideal destination for families, nature enthusiasts, and anyone seeking a peaceful retreat. At Allen Heights Park, you'll find beautifully landscaped grounds, lush greenery, and tranquil walking paths that invite you to unwind and connect with nature. Our well-maintained playground provides a fun and safe environment for children to explore and enjoy, while the open fields are perfect for picnics, casual sports, or simply soaking up the sun.

Welcome to Camp Arrow Wood, your premier destination for outdoor adventure and relaxation in the heart of the Berkshires! Nestled at 195 Cloverdale Street, Pittsfield, Massachusetts, our camp offers a serene escape from the hustle and bustle of everyday life. Whether you're seeking a weekend getaway, a summer retreat, or a place to connect with nature, Camp Arrow Wood is the perfect spot. Our beautiful grounds boast a variety of amenities and activities for all ages. Explore our extensive hiking trails, enjoy a leisurely paddle on our scenic lake, or challenge yourself with our ropes course and climbing wall. For those looking to unwind, our tranquil setting provides the ideal backdrop for meditation, yoga, or simply soaking in the natural beauty.

The Heart of the Berkshires Motel is a charming lodging option located at 970 West Housatonic Street in Pittsfield, Massachusetts. Situated in the heart of the picturesque Berkshires region, this motel offers cozy and comfortable accommodations for travelers looking to explore the natural beauty and cultural attractions of the area. With a convenient location and friendly staff, the Heart of the Berkshires Motel is the perfect place to relax and unwind during your visit to the United States.

Welcome to Lake Onota Village, your serene retreat nestled in the heart of the Berkshires at Lakewood Drive, Pittsfield, Massachusetts. Our beautiful location offers a unique blend of lodging and RV park facilities, making it the perfect destination for nature lovers and adventure seekers alike. Surrounded by the scenic beauty of Lake Onota, our village provides a tranquil setting for relaxation and exploration. At Lake Onota Village, we pride ourselves on offering comfortable accommodations that cater to a variety of preferences. Whether you're traveling in your RV or looking for a cozy cabin stay, our well-equipped facilities ensure a memorable and enjoyable experience. Our spacious RV park features modern amenities, including full hookups, clean restrooms, and picnic areas, all designed to enhance your stay.

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.

The Berkshire Inn is a charming lodging establishment located at 150 West Housatonic Street in the picturesque town of Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's many attractions, including cultural venues, outdoor activities, and charming shops and restaurants. Whether visiting for business or pleasure, the Berkshire Inn is the perfect home away from home for travelers seeking a relaxing and enjoyable experience in the beautiful Berkshires region.

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.

Burbank Park is a picturesque outdoor oasis located at 256 Lakeway Drive in Pittsfield, Massachusetts, United States. This charming park offers visitors a serene escape from the hustle and bustle of everyday life, with beautiful green spaces, walking trails, and stunning views of the surrounding landscape. Whether you're looking to enjoy a leisurely stroll, have a picnic with family and friends, or simply relax and unwind in nature, Burbank Park is the perfect destination. With its tranquil atmosphere and natural beauty, this park is a beloved community gem that provides a peaceful retreat for all who visit.

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.

Berkshire Trips is a premier travel agency located at 212 Fenn Street in Pittsfield, Massachusetts. We specialize in creating unforgettable experiences in the picturesque Berkshire region of the United States. Our knowledgeable and friendly staff are dedicated to providing top-notch customer service and helping you plan the perfect getaway. Whether you're looking for a relaxing weekend retreat, an adventure-filled outdoor excursion, or a cultural exploration of the area's rich history and arts scene, Berkshire Trips has you covered. Contact us today to start planning your next unforgettable journey in the beautiful Berkshires.

Welcome to MP & Beefy Crane Park, your tranquil oasis nestled in the heart of Pittsfield, Massachusetts. Conveniently located at 100 Dartmouth Street, our park offers a serene escape from the hustle and bustle of everyday life. Whether you're looking to enjoy a leisurely stroll, a family picnic, or simply relax amidst nature, MP & Beefy Crane Park provides the perfect setting. Our beautifully landscaped grounds are ideal for outdoor activities, community gatherings, and personal reflection. Come and explore the peaceful atmosphere and natural beauty that make MP & Beefy Crane Park a cherished destination for locals and visitors alike. We look forward to welcoming you to our little slice of paradise in Pittsfield!

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.

Welcome to Allendale Pines MHC, your premier destination for comfortable and convenient lodging in the heart of the Berkshires. Nestled at 245 Cheshire Road in Pittsfield, Massachusetts, our RV park offers a serene and picturesque setting, perfect for both short visits and extended stays. Whether you're traveling in an RV or seeking a peaceful getaway, Allendale Pines provides a welcoming environment with modern amenities to meet all your needs. Our park features spacious sites equipped with full hookups, ensuring a hassle-free experience for all our guests. Enjoy the tranquility of our beautifully landscaped grounds, complete with walking paths and picnic areas that allow you to immerse yourself in nature. Conveniently located near local attractions, dining, and shopping, Allendale Pines MHC serves as an ideal base for exploring the vibrant culture and scenic beauty of the Berkshires.

Berkshire Community College Property is a beautiful park located in Pittsfield, Massachusetts, United States. This serene and picturesque institution offers a peaceful retreat for students and visitors alike. The park features lush greenery, walking paths, and outdoor seating areas, making it the perfect place to relax and unwind. Whether you're looking to study outdoors, enjoy a picnic with friends, or simply soak up the natural beauty of the Berkshires, Berkshire Community College Property is the ideal destination. Come and experience the tranquility and charm of this lovely park in the heart of Pittsfield.

The Central Downtown Inn & Suites is a charming lodging option located at 20 West Housatonic Street in the heart of Pittsfield, Massachusetts. Our cozy inn offers comfortable accommodations and modern amenities for both leisure and business travelers. Conveniently situated in the bustling downtown area, guests can easily access local attractions, shops, and restaurants. Whether you are visiting for a weekend getaway or an extended stay, The Central Downtown Inn & Suites provides a relaxing and welcoming atmosphere for all guests.

Fly Tringo is a premier travel agency located at 443 Crane Avenue in Pittsfield, Massachusetts. Our team of experienced travel experts are dedicated to providing exceptional service and personalized travel solutions to our clients. Whether you're planning a family vacation, romantic getaway, or business trip, Fly Tringo has you covered. From booking flights and accommodations to organizing tours and activities, we handle all the details so you can relax and enjoy your journey. Contact us today to start planning your next adventure!

Anywhere Anyway Travel is a premier travel agency located on First Street in Pittsfield, Massachusetts. Our experienced team of travel experts is dedicated to helping you plan the perfect getaway, no matter where you want to go or how you want to get there. From booking flights and accommodations to organizing tours and excursions, we can handle all the details so you can relax and enjoy your trip. Let Anywhere Anyway Travel turn your travel dreams into reality.

Welcome to R&S Traveler's, your trusted travel agency located at 43 Adam Street, Pittsfield, Massachusetts. We are dedicated to crafting personalized travel experiences that cater to your unique needs, emotions, passions, and budget. Our team of experienced advisors is committed to knowing you and ensuring your travel dreams come true. At R&S Traveler's, we understand that every traveler is different, which is why our advisors work closely with you to build vacations tailored just for you. We strive to find the best value for your budget, offering exclusive upgrades, added amenities, and excursions that perfectly match your personality.