Vacation rentals in Chapel Falls

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Top-rated vacation rentals in Chapel Falls

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A historic farmhouse is set amidst lush greenery, with a well-maintained garden featuring colorful flowers. A sign invites visitors, while a vintage cart enhances the rustic charm. The surrounding landscape offers distant views of rolling hills under a partly cloudy sky.
Farm stay in Williamsburg
4.99 out of 5 average rating, 151 reviews

Charming, updated , 3 bedroom farmhouse farm stay

Enjoy a tranquil stay on a small market farm. Winter is coming and we are midway between Berkshire East Ski Resort and the nightlife of Northampton. Plenty of great local cross country and snow shoe trails as well as snow mobile circuits and destinations. Dog-sledding! Enjoy beautiful evening skies while sitting around the fire pit. Mingle with the goats and ducks (duck eggs usually available) . Conveniently located to Northampton, Amherst, the 5 colleges, restaurants and family activity.

Top guest favorite
Guesthouse in Cummington
4.99 out of 5 average rating, 220 reviews

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Top guest favorite
An expansive view of rolling hills and distant mountains is visible through a treeline, with a foreground of manicured green grass and apple trees. The cabin's wooden structure is partially seen on the right, enhancing the connection to nature.
Cabin in Williamsburg
4.97 out of 5 average rating, 131 reviews

Mountain Retreat close to Northampton & Amherst!

Come have this mountain top home situated on 150 secluded acres in beautiful historic Williamsburg all to yourselves!! If you want privacy within 10-20 minutes from Northampton, Hadley, and Amherst, then this cabin is perfect. Within walking distance, you will have access to trail systems for either your hiking or biking endeavors. You can stay and enjoy the peaceful nature of our home, sit on the massive deck while you gaze upon breathtaking views of the Pioneer Valley, or venture out.

Guest favorite
A wooden deck extends from the back of the house, overlooking a fire pit surrounded by several adirondack chairs. Vibrant fall foliage complements the tranquil setting, with a winding path leading to the house, where large windows invite natural light.
Chalet in Charlemont
4.97 out of 5 average rating, 149 reviews

Ski, Raft & Relax | Lodge w/ Pool Table & Fire Pit

On your journey to The Lodge on Warner Hill, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located 10 minutes from Berkshire East and the Deerfield River

Top guest favorite
A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.
Apartment in Northampton
4.97 out of 5 average rating, 490 reviews

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

Top guest favorite
The living room features a high, vaulted ceiling with large, triangular windows allowing ample natural light. A brick fireplace serves as a focal point, surrounded by a wooden mantel and decorative plants. A dining table sits nearby, and hardwood flooring is complemented by colorful area rugs.
Farm stay in Ashfield
5.0 out of 5 average rating, 153 reviews

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

Guest favorite
A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.
Home in Ashfield
4.97 out of 5 average rating, 106 reviews

An 18th century farmhouse

Built in 1785 this antique Cape was carefully restored to its original design about 20 years ago. The house is set on a quiet road in the middle of fields, woods, gardens, and hiking trails. it is secluded with easy access to the natural world. The rooms are book-lined and filled with family objects. It is close to Berkshire East for skiing and snowboarding in the winter and whitewater rafting and swimming in the summer. Mass MoCA and the Clark Museum are within an easy drive.

Top guest favorite
A well-maintained home is situated on a gentle slope, featuring a neatly landscaped front yard with flowering plants and shrubs. An American flag is displayed by the entrance, and a gravel driveway leads to the garage below, surrounded by lush greenery.
Home in Amherst
5.0 out of 5 average rating, 181 reviews

The Suprenant House

Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.

Top guest favorite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Apartment in Conway
4.96 out of 5 average rating, 223 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Top guest favorite
A row of trees with vibrant autumn leaves stands against a clear blue sky. The sunlight filters through the branches, creating a warm glow, while long shadows stretch across a field blanketed in fallen leaves.
Farm stay in Ashfield
4.98 out of 5 average rating, 105 reviews

Blue House Farm and Gardens

Your lovely peaceful Studio shares a wall with our 1794 farmhouse but has its own entrance, porch and privacy. Enjoy the tranquility of our land but still be only 2.4 miles from the center of Ashfield, 30 minutes from Northampton and Old Deerfield, less than 20 minutes to Berkshire East Mountain Resort, 30 minutes to Notchview for cross country skiing and snowshoeing, and 45 minutes to Mass. MOCA.

Top guest favorite
The charming exterior of the 18th-century farmhouse features yellow clapboard siding and a classic red front door. Symmetrical windows line the facade, surrounded by a manicured lawn and the shade of nearby trees.
Farm stay in Whately
5.0 out of 5 average rating, 38 reviews

Beautiful 18th Century Farmhouse

Enjoy the beauty of a bygone era while staying in this 18th-century farmhouse, located on the historic Quonquont Farm property, a working farm and orchard. The building has been lovingly restored with custom raised paneling and antique details, and is beautifully decorated with period furniture. The house overlooks a quiet, maple-lined street in a peaceful and secluded area just minutes from 91.

Top guest favorite
A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.
Cabin in Plainfield
4.92 out of 5 average rating, 258 reviews

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

Popular amenities for Chapel Falls vacation rentals