Beachfront holiday rentals in Berkshire County

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Top-rated beachfront rentals in Berkshire County

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

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Cabin in Plainfield

4.63 out of 5 average rating, 70 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

Guest favourite

Cottage in Becket

4.82 out of 5 average rating, 57 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.

Top guest favourite

Cottage in Hinsdale

4.99 out of 5 average rating, 157 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.

Guest favourite

Home in Otis

4.97 out of 5 average rating, 34 reviews

Big Pond Hideaway

Tucked deep in the woods at the end of a winding dirt road, Big Pond Hideaway is a peaceful retreat steps from Big Pond, a 300-acre lake for fishing, swimming, and kayaking. Updated throughout, the home is bright and airy with lake views. A fully equipped kitchen makes cooking easy. As the sun sets, grill on the deck, gather around the fire pit under the stars, or sip a cocktail on the dock. Whether paddling or soaking in the quiet, memories await. Escape the noise. Find your hideaway.

Superhost

Home in Becket

4.93 out of 5 average rating, 156 reviews

Lake front retreat - Stylish Berkshire home

Absolute privacy! Escape to this beautifully renovated mid-century home w/ 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly retreat offers exclusive lake frontage complete w/ a dock & 4 kayaks for endless fun! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Located just 20 mins from Downtown Lee, outlets, hikes, & Otis Ridge skiing

Home in Pittsfield

4.93 out of 5 average rating, 41 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.

Guest favourite

Cottage in Becket

4.93 out of 5 average rating, 229 reviews

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

Guest favourite

Home in Becket

4.94 out of 5 average rating, 34 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!

Guest favourite

Flat in Otis

4.95 out of 5 average rating, 108 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.

Barn in Stockbridge

4.58 out of 5 average rating, 12 reviews

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.

Top guest favourite

Flat in Williamstown

5 out of 5 average rating, 135 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.

Home in Otis

4.58 out of 5 average rating, 24 reviews

Lake house in the heart of the Berkshires

Enjoy a beautiful, serene getaway nestled in the heart of the Berkshires. Waking up steps to a clean, clear, spring fed lake, this is the perfect vacation spot for all seasons. This lakefront paradise is 30 minutes from the Kripalu center for Yoga and Health, Tanglewood music festival and Butternut skiing. We're only a short 15 minutes from the Jacob's Pillow Dance Center and Otis Ridge ski area.