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.

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Guest favorite

Home in Catskill

4.96 out of 5 average rating, 137 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access. We provide kayaks, SUP & complimentary tours of the Hudson by boat! Enjoy your private sauna & steam shower indoors and hot tub on lower deck - all for your exclusive use. Fish right off the property. Enjoy dinner in the Gazebo suspended over the Hudson. The area serves up plenty-Saugerties, Woodstock, Hudson, Hunter, Catskill. Honestly you'll not want to leave.

Guest favorite

Guesthouse in Germantown

4.94 out of 5 average rating, 313 reviews

The Studio at Pear Farm

Sophisticated large studio has gorgeous light and Catskill Mountain Views Formally an artist studio, it has undergone an elegant renovation. The luxurious bathroom features premium tile and a glass walled shower The kitchen is new, nicely equipped and has a full sized refrigerator. Enjoy outdoor grilling and dining on the private deck. The studio is located on 65 pristine acres fronting directly on the Hudson River. 5 minutes to Germantown. 10 minutes to Tivoli, Hudson or Bard College.

Guest favorite

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.

Superhost

Cottage in Florida

4.83 out of 5 average rating, 105 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

ENJOY A MOUNTAIN ADVENTURE!We got new doors & mattresses!!! You will fall in love with this magic cottage nestled within 2 acres of old growth forest. Breathe in the fresh air enjoying the mountain vistas & sipping some hot cocoa or a glass of wine. Relax by the pellet stove or gaze at the stars by the fire pit while you hear the water run from the stream across. Enjoy the Berkshire East Ski, the famous hairpin turn, national forests, MASS MoCA, Mt. Greylock and many outdoor adventures nearby.

Guest favorite

Cabin in Freehold

4.96 out of 5 average rating, 162 reviews

Tiny Home A-Frame with Hot Tub & Creek

Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our brand new home has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to WFH.

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Guest favorite

Home in Huntington

4.9 out of 5 average rating, 111 reviews

Private house on the River

Get away from it all at this very private house on the Westfield River. Walk in and feel right at home in this comfortable 2 bedroom ranch. It has a large back porch with outdoor seating and table that is 50 steps from the river. We supply everything you need, from the sheets and towels to your basic cooking needs. All you need to do is the bring the food. This house is perfect for families, with a large yard, indoor and outdoor toys, tire swing, floats, pack & play and high chair.

Guest favorite

Home in Kingston

4.98 out of 5 average rating, 219 reviews

DeMew House in Historic Kingston

PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive, newly renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Guest favorite

Bungalow in Cairo

4.99 out of 5 average rating, 313 reviews

Swim just feet from your door, 20 min to Hudson

Modern Scandinavia-style riverfront home on 8 acres w tons of privacy. 20 min from Hudson. Sit on your porch for coffee/drinks/dinner filled w sounds of a rushing river, or walk across the river into your own private swimming pond! Perfect for a nature retreat, hiking, swimming, fishing, skiing, the solo parent escape to recharge, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Hate has no home here-all are welcome.

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 133 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.

Guest favorite

Cabin in Lee

4.9 out of 5 average rating, 102 reviews

Spring sale! Cabin with views in the Berkshires

The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!

Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 252 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016), 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.