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

A firepit area is surrounded by several light blue chairs, set on a pebbled ground. The calm lake reflects the trees and landscape, creating a serene outdoor space ideal for gathering and relaxation.

Cottage in Becket

4.94 out of 5 average rating, 209 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

The exterior of the lakefront home is displayed, featuring a two-story structure surrounded by greenery. A well-maintained lawn and rock garden enhance the inviting landscape. A shed is visible to the right, adding practical space to the property.

Home in Pittsfield

4.97 out of 5 average rating, 117 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!

Top guest favorite

A scenic view is captured from a deck, showcasing a calm pond reflecting vibrant autumn foliage. A rustic vase of flowers is placed on a railing, while the sky displays a gradient of soft pinks and purples as the sun sets behind the hills.

Place to stay in Leeds

4.98 out of 5 average rating, 141 reviews

The Ice House on Mill Pond

Escape to this picturesque setting nestled along the Catskill Creek, with private deck and awe-inspiring views of the pond, cliffs and rapids. Whether seeking a serene romantic getaway or a chance to recharge, this unique spot provides a harmonious blend of comfort and nature. Immerse in the soothing flow of nature and indulge in some of the best offerings in the Hudson Valley. Inside, the house is clean and cozy, providing the ideal haven to unwind and reconnect with your surroundings.

Top guest favorite

A serene view of a stream surrounded by trees that display autumn foliage in warm hues. A deck area with comfortable chairs is visible by the water, providing a peaceful spot for relaxation amidst the natural landscape.

Chalet in Dover

4.97 out of 5 average rating, 116 reviews

Mountain Chalet: Private Brook - Hot Tub - Firepit

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 114 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Guest favorite

The kitchen area features a light countertop with modern cabinetry and a stylish backsplash. A coffee maker, dish drying rack, and sink are visible. Organized jars hold various kitchen supplies, creating a functional and tidy space for meal preparation.

Camper/RV in Westhampton

4.89 out of 5 average rating, 169 reviews

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Guest favorite

A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.

Cottage in Lanesborough

4.84 out of 5 average rating, 279 reviews

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is 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. Sleeps 6. Ther are two full and one 1/2 baths.

Guest favorite

The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.

Cabin in Newfane

4.99 out of 5 average rating, 277 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Guest favorite

A charming cabin exterior features a wooden porch with a yellow door. Stone pathways lead to the entrance, surrounded by landscaped greenery. Natural lighting highlights the rich wood beams and inviting seating area, while vibrant foliage of the forest provides a serene backdrop.

Cabin in East Nassau

4.99 out of 5 average rating, 104 reviews

Artistic Blue Cabin with private creek and forest

Our wood cabin is located in a secluded area on 5 acres of forest and a creek flowing through the property that you see from every room. Newly renovated, our cabin is finished with refined colonial details and decorated with furniture from all over the world. Enjoy a morning coffee with a view of the creek by the wood burning stove or take a hike through our 5 acres of backyard forest. This property is the perfect escape.

Top guest favorite

A spacious bedroom features a large window with a view of the lush greenery outside. The bed is adorned with a mix of pillows and a colorful area rug rests on the floor, enhancing the room's serene atmosphere.

Cabin in Lee

4.91 out of 5 average rating, 123 reviews

Secluded Berkshire cabin with scenic views

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!

Guest favorite

A cozy seating area is illuminated by natural light from two windows, featuring a blue couch and an orange chair. A decorative rug with a circular pattern anchors the space, while a trunk serves as a coffee table. A plant adds a touch of greenery.

Cottage in Lanesborough

4.93 out of 5 average rating, 145 reviews

The Sail Loft

Cozy, private house from 1850, located in the heart of the Berkshires. On a quiet street across from a pond, the cottage has access to the Ashuwillticook rail trail. Relax on the private back porch, or in the large bath tub. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer. Close to several downhill and cross country ski spots, hiking trails and Tanglewood!

Superhost

A vibrant red yurt is nestled among the trees, surrounded by autumn foliage. A wooden platform supports the yurt, while a vehicle is parked nearby. A light plume of smoke is seen rising from the woodstove, indicating warmth inside.

Yurt in Stephentown

4.9 out of 5 average rating, 126 reviews

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!