Beachfront holiday rentals in Berkshire County

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Berkshire County

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

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Lake front retreat - Stylish Berkshire home

Experience total privacy at this beautiful mid-century home with 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly getaway offers exclusive lake frontage, complete with a dock & 4 kayaks for endless adventures! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Just 15 minutes from Downtown Lee, close to outlets, hiking trails, and Otis Ridge skiing!

WalkabilityBeachQuiet

4.92 out of 5 average rating, 182 reviews

Superhost

A covered porch area features two sturdy chairs positioned for comfort, overlooking the lawn and scenic pond. Green grass and picnic tables provide additional space for relaxation, while the landscape is framed by a wooden railing, enhancing the view of the calming water and surrounding nature.

Cabin in Plainfield

Camp on Windsor Pond- Berkshires

Relax at this peaceful 3 bedroom camp right on Windsor Pond. Camp has views of the beautiful pond where you can fish, swim, kayak/canoe in. The camp also comes with access to the private beach across the street. Located on the Berkshire and Hampshire county line you are 30 minutes or less away from places including Berkshire East, Zoar, Mt Greylock, Mass MoCA, and plenty of local ponds & state forests. Cell service is great for folks with AT&T. Service may be spotty for others. Wifi available

WalkabilityBeachDecor

4.71 out of 5 average rating, 102 reviews

Top guest favourite

A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.

Cottage in Hinsdale

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

BeachWalkabilityGetting around

4.99 out of 5 average rating, 170 reviews

Top guest favourite

The exterior of the home is illuminated at dusk, showcasing a multi-level structure with numerous large windows. The well-maintained lawn features stone pathways, and outdoor seating areas are visible. Surrounding trees offer a natural backdrop, enhancing the tranquil setting.

Home in Pittsfield

Lakefront home in the heart of the Berkshires

Lakefront, close to skiing, hiking, restaurants, Tanglewood and everything the Berkshire county has to offer. 4 bed/4 bath and additional sleeping area in lower level. Large open layout with two living areas overlooking the lake. Master bedroom with a wall of windows and amazing views, balcony. Three decks to enjoy the views and a patio with built in firepit for colder nights. Jiminy peak skiing 20 min, Tanglewood 20 min, Berkshire Museum 10 min, and lake, dock, and kayaks right outside.

ViewConditionValue

4.94 out of 5 average rating, 48 reviews

Guest favourite

A firepit area is surrounded by several light blue chairs, set on a pebbled ground. The calm lake reflects the trees and landscape, creating a serene outdoor space ideal for gathering and relaxation.

Cottage in Becket

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

WalkabilityBeachNearby

4.92 out of 5 average rating, 302 reviews

Guest favourite

Cottage in Becket

Cozy Cottage-Fall foliage on the Lake!

Relax in our rustic lake-front cottage for your next getaway in the Berkshires! Our small lake is perfect for kayaking, fishing, or just enjoying in any season. Come by in the Fall to soak in the stunning color reflecting off the lake. In the Winter, light up the fireplace after skiing nearby at Otis Ridge slope. Whether you want cook s'mores by the water, hike the Appalachian Trail, visit Berkshire towns, or just get away, we welcome you. Please Note-Animals not allowed.

BeachViewParking

4.79 out of 5 average rating, 63 reviews

Top guest favourite

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.

Flat in Otis

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.

ViewWalkabilityGetting around

4.96 out of 5 average rating, 137 reviews

Guest favourite

The interior space features a white armchair beside a decorative wooden stool and a black coffee table. A tall ladder leads to the lofted area, while a metal shelving unit displays a framed image of a cow and a plant. Exposed wooden beams complement the natural decor.

Home in Egremont

Modern and Stylish Country Lakeside Cottage

Direct view of and use of waterfront. One king bedroom, one bath, cook's kitchen with high end appliances. Banquette seating surrounded by banks of windows. Large living room with gas fireplace. Small loft area above living room with queen bed. Cathedral ceilings. Large bath en suite. Washer/Dryer. Patio and fire pit for marshmallows. Boat/swim in summer or ice fish/skate in winter. A perfect spot to enjoy the outdoors. Stone’s throw from Catamount and Butternut.

WalkabilityViewComfort

4.91 out of 5 average rating, 88 reviews

Home in Chester

The Brook House | Private Woodland Retreat

Escape to The Brook House, a private woodland retreat in the peaceful hills of western Massachusetts. Surrounded by woods and nature, this comfortable country home is perfect for a quiet getaway, family weekend, or base for exploring the Berkshires. Enjoy spacious living areas, a fully equipped kitchen, reliable Wi-Fi, self check-in and plenty of privacy. Hike, explore nearby towns, or simply slow down and enjoy the quiet of the Massachusetts Hilltowns.

CleanlinessComfortDecor

5.0 out of 5 average rating, 3 reviews

Guest favourite

A spacious bedroom features a queen bed dressed in patterned bedding. A warm area rug covers the hardwood floor. A cozy chair and a standing lamp are positioned beside the bed. Natural light filters through curtains, illuminating the room's simple decor.

Private room in Pittsfield

Pittsfield. Large queen bedroom, second floor.

This 2nd floor bedroom is in the host's and her dog's home. Besides a queen bed with a comfortably firm foam mattress, it has a work table, sitting area, double closet, and large dresser with mirror. Guests have kitchen privileges, welcome access to living room tv, deck overlooking gardens, and basement laundry room. A mile away is lovely Onota Lake. It's only a short drive to downtown Pittsfield. Nearby are many cultural & natural sites.

WalkabilityViewKitchen

4.96 out of 5 average rating, 51 reviews

A private entrance is showcased, featuring a mint green door with a decorative glass window. Steps lead up to the door, framed by rustic wooden walls and overhead light fixtures. The wooden deck is warmly illuminated, inviting access to the charming modern unit.

Barn in Stockbridge

LAKE COTTAGE -In the Berkshire/ walk to Tanglewood

BRAND NEW! Very charming modern one-bedroom unit created within historic 1860 barn. All modern conveniences --lightening-fast internet/WIFI/cable TV/central A/C/washer/dryer and efficient kitchen. Furnished with mid-century classic pieces. Discounts for longer term stays. Private entrance with yard for outside dining. Within walking distance to Tanglewood concerts and Stockbridge Bowl. Views of conservation-protected open field.

WalkabilityAccuracyDecor

4.58 out of 5 average rating, 12 reviews

Top guest favourite

A spacious wooden deck features two comfortable Adirondack chairs facing the tranquil lake. Lush trees surround the area, providing shade and a natural setting, while the calm water glimmers through the foliage.

Home in Tolland

Lakefront Retreat at Porcupine Place

Welcome to Porcupine Place, a serene retreat nestled in the private lake community of Wildwood, a gated lake community in the foothills of the Berkshires. Immerse yourself in nature or embark on exciting adventures with your loved ones. Whether it's hiking scenic trails, cruising on the lake, or simply soaking in the breathtaking landscape, Porcupine Place is your perfect lakeside getaway.

ViewBeachSleep quality

5.0 out of 5 average rating, 49 reviews