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Beachfront vacation 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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Home in Monterey

5 out of 5 average rating, 3 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

Renovated Modern Ski chalet 7min from Butternut ski resort, 15 min from catamount ski resort, 5BR 4Bath 2LR Lake Garfield w Hot tub, near Great Barrington. Fronting Lake Garfield 5 min walk from public beach lake access and a variety of activities in the Berkshires, the house can comfortably accommodate up to 14 people. 5 Bedrooms, 4 full Bathrooms, 2 LRs, Dining Room and Front & Rear Decks. Year-round Hot Tub and Solo smokeless Fire Pit, BBQ & Picnic table, deck furniture. Pets =$400 per pet

Cottage in Becket

4.94 out of 5 average rating, 171 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

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 • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • 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

Home in Becket

4.93 out of 5 average rating, 138 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

Cabin in Plainfield

4.66 out of 5 average rating, 58 reviews

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

Cottage in Becket

4.81 out of 5 average rating, 52 reviews

Cozy Cottage 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 the nearby hills or sledding the Knox Trail. 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.

Cottage in Hinsdale

4.99 out of 5 average rating, 152 reviews

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.

Home in Becket

4.95 out of 5 average rating, 59 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

Escape the hustle and unwind at this unique, tranquil octagonal retreat in the Berkshires. Set on 14 acres of private woodland, the stylish main house comfortably sleeps 3-4, while the charming bunkhouse accommodates an additional 4-5 guests. Enjoy a red cedar barrel sauna, outdoor shower, and exclusive access to Center Pond Beach, offering the perfect setting to relax and unplug. 10 minutes to Jacobs Pillow Dance, 20 minutes to top-notch theaters and restaurants, 30 minutes to ski resorts.

Home in Becket

4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

House is right on the lake! Step into the water or the dock from the private flat yard! Enjoy the amazing lake view from the patio or the glass sunroom! Located in the heart of the Berkshires - 10 mins from Jacob's Ladder, 20 mins from Lee Outlets, and 30 mins from the Norman Rockwell Museum or Tanglewood. Enjoy farm-to-table restaurants in the area, or make home-cooked meals using the well-equipped kitchen. House is surrounded with trees and perfect for a quiet and relaxing getaway!

Rental unit in Otis

4.95 out of 5 average rating, 88 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.

Home in Otis

4.96 out of 5 average rating, 28 reviews

Big Pond Hideaway

Truly off the beaten path at the end of a winding dirt road, Big Pond Hideaway is a quiet and secluded lakefront retreat tucked away in the woods, less than 100 steps from beautiful Big Pond, a 300 acre fish filled lake. Recently renovated with lots of windows and views of the lake, it is stylish, bright and open with an updated kitchen & appliances, gas stove, grill, wood stove, outdoor shower and plenty of outdoor seating on the decks or around the patio fire-pit.

Home in Egremont

4.93 out of 5 average rating, 72 reviews

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.

Rental unit in Williamstown

5 out of 5 average rating, 114 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

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Popular amenities for Berkshire County beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Home in Becket

4.95 out of 5 average rating, 59 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

Cabin in Plainfield

4.66 out of 5 average rating, 58 reviews

Camp on Windsor Pond- Berkshires

Rental unit in Otis

4.95 out of 5 average rating, 88 reviews

Enjoy every season the Berkshires have to offer.

Home in Monterey

4.8 out of 5 average rating, 66 reviews

Rustic 3bd Lake Front Country Cottage

Home in Egremont

4.93 out of 5 average rating, 72 reviews

Modern and Stylish Country Lakeside Cottage

Home in Monterey

5 out of 5 average rating, 3 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

Private beachfront home rentals

Home in Becket

4.93 out of 5 average rating, 138 reviews

Lake front retreat - Stylish Berkshire home

Barn in Stockbridge

4.58 out of 5 average rating, 12 reviews

LAKE COTTAGE -In the Berkshire/ walk to Tanglewood

Cottage in Becket

4.81 out of 5 average rating, 52 reviews

Cozy Cottage on the Lake

Home in Egremont

4.93 out of 5 average rating, 72 reviews

Modern and Stylish Country Lakeside Cottage

Cottage in Hinsdale

4.99 out of 5 average rating, 152 reviews

Cozy Cottage in the Berkshires

Home in Tolland

5 out of 5 average rating, 24 reviews

Lakefront Retreat at Porcupine Place

Home in Becket

4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

Home in Becket

4.95 out of 5 average rating, 59 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

Luxury beachfront home rentals

Home in Pittsfield

4.93 out of 5 average rating, 40 reviews

Lakefront home in the heart of the Berkshires

Home in Becket

4.93 out of 5 average rating, 138 reviews

Lake front retreat - Stylish Berkshire home

Home in Monterey

5 out of 5 average rating, 3 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

Home in Otis

4.58 out of 5 average rating, 24 reviews

Lake house in the heart of the Berkshires

Destinations to explore