Guesthouse vacation rentals in Berkshire County

Black Bear Bungalow, Minutes from Tanglewood

This private guest house with full kitchen, living area and large bedroom with Luxurious Queen bed and plenty of storage only 10 miles to Ski Resorts. Sheffield, Mass. is only 5 miles to Great Barrington with wonderful shops, restaurants and grocery stores. You will have a FULL SIZE kitchen in this wonderful guest house. The first level has a full size kitchen, living area with recliners and TV, large bath and laundry. Upstairs is a large bedroom with queen bed. This is a 2 person guest home.

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Warm Luxury | Steam Sauna, Heated Floors, Ritz Bed

Winter Wellness Escape in the Berkshires | Treat yourself to a cozy, luxury retreat in the heart of the Berkshires—your private spa sanctuary with a steam sauna, radiant heated floors, and the iconic Ritz-Carlton bed. Perfect for romantic getaways, creative recharge trips, or restorative winter weekends. Welcome to Mt. Williams Retreat, a designer guest cottage just two blocks from Williams. Featured in Insider Home, this refined escape blends wellness, design, and comfort in every detail.

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

The Carriage House: Spotless, Charming 2 Bedroom

The 1820 Carriage House is in the heart of the beautiful Berkshires. Williamstown and Mass MoCA are up the road, Lenox is to the south, and Mount Greylock is around the corner. It's a fully equipped 950 square foot cottage, light, airy, charming and immaculate, conveniently located in Lanesborough. With seven rooms, two stories, a comfy queen and full-sized bed, full kitchen, washer/dryer and off-street parking, your Berkshire visit will be as comfortable as it is memorable.

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.

The Blue Jay Cottage

Come stay at our cozy Blue Jay Cottage. Everything you need to feel comfortable and at home. It is an idyllic setting for your next romantic getaway or your home base while you explore the local area and enjoy all that the Berkshires have to offer. The cottage features a completely renovated kitchen with new appliances, free in unit washer and dryer, a spacious private back deck with a tranquil view of the garden. Free off street parking.

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

The Little House: A Cozy Cottage Guest House

Cozy cottage guest house nestled in the countryside. This tiny house is perfect for a couple or the solo traveler looking to escape into the tranquility of the beautiful Berkshires. Close to all of the modern conveniences and yet tucked away, we are minutes from the Appalachian Trail, on a historic property that once hosted Mark Twain for two summers. Kick back and relax in this calm, clean, stylish space.

Country Cabin

Lovely private country setting, air conditioner. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. The space is for 2 adults but I'm flexible, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.