
Holiday rentals in Hawley
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Top-rated holiday rentals in Hawley
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Tall Pines Rental | Pet Friendly | Fire Pit | Yard
Private, Pet-Friendly Charlemont getaway on 3 wooded acres with Pelham Brook in the backyard. • 10 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.
4.96 out of 5 average rating, 80 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 !
5.0 out of 5 average rating, 201 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.
4.86 out of 5 average rating, 123 reviews
Berkshire Mountain Top Chalet
Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.
4.93 out of 5 average rating, 193 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.
4.94 out of 5 average rating, 34 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
4.97 out of 5 average rating, 150 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.
4.98 out of 5 average rating, 109 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.
4.97 out of 5 average rating, 109 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.
4.94 out of 5 average rating, 16 reviews
Sunny, light filled loft in 1873 Colonial
Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!
4.97 out of 5 average rating, 310 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.
4.96 out of 5 average rating, 227 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.
4.78 out of 5 average rating, 49 reviewsPopular amenities for Hawley holiday rentals
Other great holiday rentals in Hawley

Stone Ridge Cottage
4.98 out of 5 average rating, 46 reviews
The Corner of Main and South St. 2 bedroom Suite.
5.0 out of 5 average rating, 60 reviews
Pondside Retreat - Entire House
4.88 out of 5 average rating, 16 reviews
Peaceful Lakeside Cabin
4.96 out of 5 average rating, 27 reviews
5BR Berkshire Home Mins To The Mountain & River
4.9 out of 5 average rating, 20 reviews
The Greylock Cabin
4.99 out of 5 average rating, 87 reviews
The Stone House
5.0 out of 5 average rating, 20 reviews
The Barn
5.0 out of 5 average rating, 21 reviewsDestinations to explore
- New York Holiday rentals
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- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Hudson Chatham Winery
- Ski Sundown
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- New York State Museum





