Waterfront vacation rentals in Berkshire County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Berkshire County

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

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Top guest favorite

Cottage in Otis

5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

Open for Summer 2025! 5 North Lake is a seasonal cottage situated yards from the shore. The property has panoramic views of the largest recreational body of water in Massachusetts: Otis Reservoir. Great for kayaking, fishing, swimming, boating or just relaxing and watching the sunset from the dock or deck. ** Our calendar is set to leave a day open after each rental to allow time to clean. If your preferred check in/out date isn’t available, message us and we’ll do our best to accommodate you!

Guest favorite

A two-level cottage is nestled among the trees, featuring a dark exterior. A private dock is visible along the water's edge, adorned with seating, while the surrounding nature reflects on the calm water, creating a serene atmosphere.

Cottage in Becket

4.94 out of 5 average rating, 197 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 • 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

Top guest favorite

A spacious deck features several lounge chairs and a table, inviting relaxation. A bright red umbrella provides shade. The tranquil lake extends in the background, with a private dock visible along the shoreline, framed by lush greenery.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

Two Adirondack chairs and a small side table are positioned on a grassy area, overlooking a serene lake. The water reflects the surrounding trees and hills, creating a peaceful atmosphere. The scene is complemented by gentle slopes of greenery in the background.

Home in Great Barrington

4.96 out of 5 average rating, 166 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Guest favorite

An open-plan living and dining area features large windows providing ample natural light. A dining table with floral-patterned chairs sits next to a cozy seating arrangement, which includes a light-colored sofa and a stylish armchair. A wooden mirror and decorative accents enhance the modern design.

Home in Becket

4.94 out of 5 average rating, 146 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

Guest favorite

Treehouse in New Marlborough

4.91 out of 5 average rating, 122 reviews

Double 3 Bedroom Tree House in the Berkshires

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

Guest favorite

A bright sitting area features a wooden daybed with a light-colored blanket. Two floral-patterned chairs accompany a small coffee table, complemented by a plant. Large glass doors open to a scenic view of the lake, and a nautical-themed chandelier illuminates the space.

Home in Otis

4.9 out of 5 average rating, 51 reviews

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Guest favorite

Home in Otis

4.96 out of 5 average rating, 108 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Superhost

A red cottage sits by the water's edge, surrounded by lush greenery. The sun deck with an umbrella overlooks the lake, and a small dock is visible nearby. A pathway leads from the cottage to the water, enhancing the serene lakeside setting.

Cottage in Egremont

4.97 out of 5 average rating, 37 reviews

Waterfront with Fun Lake Toys, Spotless!

Amenities: 3 bedroom, 1 bath (sleeps 5 max), waterfront cottage on Prospect Lake with a sun deck, bar, 2 kayaks, 2 canoes, 1 paddle board, fishing rods, 2 outdoor dining areas, dock with swim ladder and lighting, waterfront seating, fire pit, propane BBQ grill, central AC, washer/dryer, dishwasher, and more! Dogs are considered with a $150 per fee (per pet) as long as they are quiet, house trained and well behaved. (There is a strict on-leash policy.)

Top guest favorite

The light blue waterfront home features a large wrap-around porch with a yellow umbrella, overlooking a sandy beach area. Colorful chairs are arranged on the porch and along the shore, creating an inviting outdoor space for relaxation and gatherings.

Home in Otis

4.95 out of 5 average rating, 158 reviews

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

Guest favorite

A sliding glass door reveals a deck overlooking a serene landscape. A green plastic chair is positioned on the wooden deck. Rain droplets can be seen on the glass, hinting at a tranquil, cozy atmosphere inside the home.

Cottage in Lanesborough

4.84 out of 5 average rating, 278 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016) CURRENTLY BEING UPDATED and RENOVATED, (March and April 2025!) private cottage set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. For conditions message Jill.

Top guest favorite

A modern kitchen is equipped with stainless steel appliances, including a refrigerator and oven. White cabinetry offers ample storage. A central island features a sink and prep space, complemented by a set of kitchen utensils. Natural light enters through a nearby window.

Apartment in Williamstown

5 out of 5 average rating, 124 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.