Waterfront vacation rentals in Pittsfield

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Pittsfield

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Valatie

4.99 out of 5 average rating, 141 reviews

Kinderhook Lake Retreat-kayaks/SUP/central air

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the bays, coves and creeks -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 106 reviews

Berkshire Pontoosuc Lake- Modern and Updated

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!

Superhost

Cottage in Hudson

4.84 out of 5 average rating, 128 reviews

Peaceful waterfront getaway near Hudson, NY

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, Chatham, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount inside an hour. Cozy wood burning stove as well as outdoor fire pit. Minimum 3 day stay.

Guest favorite

Home in Athens

4.93 out of 5 average rating, 114 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Superhost

Cottage in Red Hook

4.9 out of 5 average rating, 201 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you. BE SURE TO SEE OUR OTHER 2 BEDROOM COTTAGE ON THE LAKE - LILY PAD - IF YOUR DATES ARE NOT AVAILABLE.

Guest favorite

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 Hillsdale

5 out of 5 average rating, 47 reviews

Lakefront close to ski & shopping

Check us out in IG @copake lake. You will love this relaxing getaway, only 2 hours north of NYC with stunning, unobstructed, year-round Copake Lake views. Dine alfresco on the upper deck or screened porch after a day of paddleboarding, swimming, boating and relaxing. Cozy up with a wood-burning fire in either the living room or tv room after skiing or snowshoeing. Take in the Hudson Valley fall foliage and explore local farms, restaurants and shopping.

Guest favorite

Home in Otis

4.97 out of 5 average rating, 104 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.

Guest favorite

Home in Egremont

4.97 out of 5 average rating, 31 reviews

Perfect Leaf Peeping Waterfront Cottage!

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.)

Guest favorite

Rental unit in Williamstown

5 out of 5 average rating, 113 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.

Guest favorite

Home in Copake

4.96 out of 5 average rating, 191 reviews

Lakefront +views +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.

Guest favorite

Home in Niverville

5 out of 5 average rating, 7 reviews

Cozy Lakeside Retreat

This peaceful, lakeside cottage is the perfect relaxing retreat for a small group looking to recharge upstate. Watch the sunrise over the lake before heading out for a morning kayak Or enjoy cocktails on the dock in the evening before heading out to explore the local towns for dinner out. This home provides the perfect place to relax and explore the bounty of the Hudson Valley.