Vacation rentals with beach access in Stockbridge

Find and book unique beach access rentals on Airbnb

Quick stats about vacation rentals with beach access in Stockbridge

  • Total vacation rentals

    Explore 10 vacation rentals in Stockbridge

  • Nightly prices starting at

    Stockbridge vacation rentals start at €128 per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Stockbridge vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Stockbridge rentals

  • 4.9 Average rating

    Stockbridge stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Stockbridge's top spots, include Norman Rockwell Museum, Naumkeag, and Berkshire Botanical Garden

Top-rated beach access rentals in Stockbridge

Guests agree: these beach access rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.
Cottage in Becket
4.95 out of 5 average rating, 319 reviews

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Guest favorite
Cabin in East Nassau
4.97 out of 5 average rating, 103 reviews

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

Top guest favorite
Home in Monterey
4.89 out of 5 average rating, 121 reviews

Berkshires Retreat w Magic View! Beach/Swim 1 mi!

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

Top guest favorite
The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.
Home in Canaan
4.99 out of 5 average rating, 118 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

Top guest favorite
A serene riverside view is framed by a bare tree, showcasing a flowing river and charming buildings along its banks. Soft natural light filters through the clouds, highlighting the peaceful landscape.
Guest suite in South Lee
4.98 out of 5 average rating, 103 reviews

Rooms on the River/free parking and WIFI

Enjoy the entire first floor in a circa 1830 house located on the Housatonic River. The apartment offers a new bath, a dining area, and a galley kitchen with a single induction cooktop, a full-sized refrigerator, oven, and microwave. We have a coffee station, and varied electrical appliances too. Convenient to Berkshires’ cultural attractions on a noted fly fishing section of the river, near golfing, hiking, kayaking, biking, and shopping. Three miles to the local grocery store & shopping.

Superhost
A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.
Home in Lee
4.93 out of 5 average rating, 104 reviews

Berkshire Vacation Home in Lee

Our spacious home is situated in a secluded neighborhood in Lee, MA (Berkshire County) and has 5 bedrooms & 2.5 baths. There is a fully equipped open concept kitchen/dining room and 2 living rooms with TVs and gas fireplaces. There is central air/heat, and a sun room that leads out to a deck overlooking our in-ground pool. Tanglewood, Antimony brewery, Balderdash winery, Hilltop Orchards, Laurel Lake, Highlawn Farm, outlets, golf, and Lenox & Stockbridge are all within a 20 minute drive.

Guest favorite
Cabin in Stockbridge
4.89 out of 5 average rating, 251 reviews

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood walls & fantastic interior design. Unwind in the reading nook, relax in the en suite bedroom with skylight, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9 minute walk or 2 minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood minutes away.

Top guest favorite
A spacious bedroom features a large bed adorned with light bedding and a folded blanket. A shelf holds decorative items alongside a serene figure. Natural light enters through sliding glass doors, leading to an outdoor patio area. A standing fan is placed nearby.
Guest suite in Great Barrington
4.99 out of 5 average rating, 136 reviews

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

Top guest favorite
A spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.
Cabin in Monterey
4.94 out of 5 average rating, 309 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

Guest favorite
Home in West Stockbridge
4.86 out of 5 average rating, 126 reviews

Peaceful Stockbridge Cabin in the Woods

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

Top guest favorite
A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.
Apartment in Otis
4.96 out of 5 average rating, 130 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Guest favorite
Home in Becket
4.94 out of 5 average rating, 132 reviews

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Popular amenities for Stockbridge beach access rentals