Vacation rentals in Hawley

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Top-rated vacation rentals in Hawley

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

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Top guest favorite
A two-story wooden house features a rustic facade with cedar shingles and a green metal roof. Large windows allow natural light into the interior. A wooden deck is accessible from the ground level, with chairs positioned on the grass nearby and a basketball hoop attached to the exterior.
Home in Charlemont
4.96 out of 5 average rating, 79 reviews

Tall Pines Rental | Pet Friendly | Fire Pit | Yard

Private, Pet-Friendly Charlemont getaway on 3 wooded acres with Pelham Brook in the backyard. • 15 minutes to Berkshire East Mountain Resort and Zoar Outdoor-ziplining, rafting, mountain biking & Mountain Coaster • Sleeps 7 | 3 bedrooms | 2 full baths * No pet fees, bring them along! • Large yard with fire pit and fire globe • Pool table, full sized screened in porch • Fully equipped kitchen & A/C We love it here, enjoy! There are numerous hiking trails, fishing, and Mt. Negus in the backyard.

Top guest favorite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Apartment in Charlemont
5.0 out of 5 average rating, 200 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

Guest favorite
An open-concept living and dining area is featured, with a wooden dining table surrounded by white chairs. A decorative area rug lies underneath. The adjacent living room is visible, showcasing a brown sofa, two armchairs, and various decorative wall art, all in a soothing color palette.
Apartment in Charlemont
4.86 out of 5 average rating, 121 reviews

Spacious apartment close to skiing and rafting

Located in the village of Charlemont, just one mile away from one of the region's favorite ski/mountain biking resorts, Berkshire East, is this charming apartment. Located on the second floor of the Wells Country Store, which was built in 1845 is a spacious, completely renovated, two-bedroom apartment. Come here for your country getaway and use this space as your launching pad for outdoor adventures. Hiking, fishing, white water rafting, skiing and so much more are right outside your door.

Guest favorite
The exterior of the cabin showcases a welcoming wooden facade with a metal roof. A stone pathway leads to a front porch with seating and flower planters. Surrounding greenery includes grass and trees, complementing the tranquil rural setting.
Home in Hawley
4.94 out of 5 average rating, 34 reviews

Berkshire Basecamp: Hike, Bike, Raft & Relax!

Welcome to our cozy retreat nestled in the picturesque Berkshires, where relaxation meets adventure! Perfectly situated near prime mountain biking trails, orchards, breweries, white water rafting and hiking! Our property features a scenic meadow and historic trees, with local wildlife including hummingbirds, ravens, blue jays, and rabbits. Perfectly situated just 9 minutes from Berkshire East Mountain Resort. The cabin combines rustic charm with modern comforts, ensuring a relaxing stay.

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

Guest favorite
A light blue two-story house is positioned along a road, featuring a covered front porch with white railings and red doors. Lush greenery frames the property, while distant mountains create a scenic backdrop.
Home in Charlemont
4.98 out of 5 average rating, 108 reviews

Red Door River House

1 min from Berkshire East Ski Mt and Thunder Mt and the Crazy Horse Bar, Across Street from Zoar Outdoor. Walk to cold river cafe and liquor store, Close to crabapple whitewater rafting. On River for Tubing, kayaking, canoeing right to and from the house. Close to Shelburne fall’s& Bridge Of Flowers outdoor rec: skiing, fishing, rafting, kayaking, zip lining and mountain biking, hiking, 5 bed + sofa bed. 4 bedrooms ,2 kings, two queens and one room- full bed. 1 full bath.1/2 bath.

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
The exterior of the rustic wooden house is shown, framed by natural greenery and landscaped shrubs. A bright orange umbrella is positioned over a deck, providing shade above a dining area. Large windows reflect the surroundings, illustrating a connection to nature.
Home in Hawley
4.94 out of 5 average rating, 16 reviews

Relaxing Mountaintop Retreat

Sitting atop the former Chickley Alps, this magical home is nestled between a XC Ski resort and conservation land. The many decks overlook the 50 acre property, which piqued the interest of acclaimed children's author, Eric Carle to build an inspiring retreat in the 1970s. Gather in the studio, where you may find some remnants of his artistic process splattered around the room. With 4 bedrooms, 2.5 baths, a workspace, and 3 distinct gathering spaces, there is room for all.

Top guest favorite
Guest suite in Charlemont
5.0 out of 5 average rating, 58 reviews

The Corner of Main and South St. 2 bedroom Suite.

This property is located just a half mile from Berkshire East Ski Resort in the scenic town of Charlemont, situated at the foothills of the Berkshires. Just a 10-minute drive to Shelburne Falls, you'll find the amazing Bridge of Flowers and Glacial Potholes. In the opposite direction, you'll find North Adams and Williamstown, home of MCLA, Williams College, Mass Moca, and Natural Bridge State Park. Both towns have trail access to Massachusett's tallest mountain, Mt.Greylock.

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.

Superhost
A charming blue house with a gable roof stands amid tall trees, surrounded by greenery. A spacious front deck invites relaxation, while large windows provide natural light to the interior. The quiet, wooded setting enhances a serene atmosphere for guests.
Home in Hawley
4.77 out of 5 average rating, 48 reviews

Flights End-Country Home with Babbling Brook, Pond

Cozy 3 Bedroom house, known as Flight's End, is for rent by night (two night minimum), weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. Many hiking trails and outdoor activities within driving distance. First floor is handicap accessible via ramp. Pets welcome but there is an additional fee of $50.

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 Hawley vacation rentals