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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Guest favourite

Home in Becket

4.93 out of 5 average rating, 118 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.

16–23 Jan

€ 370 per night

Guest favourite

Home in Becket

4.96 out of 5 average rating, 50 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

Take a break from the hustle at this unique and tranquil getaway in the Berkshires. This stylish octagonal home boasts a main house which sleeps 3-4 and a bunk house which sleeps an additional 4-5 guests. With 14 acres of beautiful private woods to explore, a red cedar barrel sauna, outdoor shower and access to center pond beach, our guests can relax, unplug and unwind. 10 minutes to Jacobs Pillow Dance, 20 minutes to amazing theater and restaurants, 30 minutes to the Berkshires best skiing.

20–27 May

€ 335 per night

Guest favourite

Cottage in Hinsdale

4.99 out of 5 average rating, 141 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.

14–21 Dec

€ 264 per night

Cottage in Becket

4.78 out of 5 average rating, 40 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.

6–13 Nov

€ 396 per night

Guest favourite

Home in Pittsfield

4.91 out of 5 average rating, 35 reviews

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.

12–19 May

€ 755 per night

Guest favourite

Home in Becket

4.88 out of 5 average rating, 17 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!

10–17 Nov

€ 262 per night

Guest favourite

Flat in Otis

4.98 out of 5 average rating, 60 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.

27 Nov – 4 Dec

€ 179 per night

Guest favourite

Home in Otis

5.0 out of 5 average rating, 26 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.

2–9 Aug

€ 641 per night

Guest favourite

Cottage in Becket

4.95 out of 5 average rating, 129 reviews

Cozy lakeside cottage

Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.

25 Sep – 2 Oct

€ 352 per night

Guest favourite

Home in Egremont

4.93 out of 5 average rating, 55 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.

1–8 Jun

€ 270 per night

Guest favourite

Flat in Williamstown

5.0 out of 5 average rating, 69 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.

1–8 Feb

€ 202 per night

Guest favourite

Home in Lee

5.0 out of 5 average rating, 6 reviews

Modern Retreat on Goose Pond

A modern 3-bedroom, 2-bathroom idyllic getaway surrounded by the Berkshires’ lush forests, mountain vistas and culture. Located on pristine Lower Goose Pond, the house is steps from the beach, shared tennis court, kayak launch and less than a mile hike to the Appalachian Trail. Drive 10-15 minutes to restaurants, shops, Tanglewood, Jacob’s Pillow, Shakespeare and Company and other Berkshire cultural attractions.

15–22 Feb

€ 501 per night