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Holiday rentals with lake access in Pittsfield

Find and book unique lake access rentals on Airbnb

Quick stats about holiday rentals with lake access in Pittsfield

  • Total holiday rentals

    Explore 30 holiday rentals in Pittsfield

  • Nightly prices starting at

    Pittsfield holiday rentals start at $112 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Pittsfield holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Pittsfield rentals

  • 5 Average rating

    Pittsfield stays are highly rated by guests—averaging 5 out of 5!

Top-Rated Accommodation with Lake Access in Pittsfield

Guests agree: These options for accommodation with lake access are highly rated for location, cleanliness and more.

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Superhost
Home in Becket

Lake front retreat - Stylish Berkshire home

Experience total privacy at this beautiful mid-century home with 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly getaway offers exclusive lake frontage, complete with a dock & 4 kayaks for endless adventures! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Just 15 minutes from Downtown Lee, close to outlets, hiking trails, and Otis Ridge skiing!

Outdoor spacesNearbyKitchen

4.92 out of 5 average rating, 181 reviews
Top Guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

NearbyOutdoor spacesComfort

4.97 out of 5 average rating, 109 reviews
Top Guest favourite
A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.
Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

NearbyOutdoor spacesCheckout

4.95 out of 5 average rating, 320 reviews
Top Guest favourite
A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.
Cottage in Hinsdale

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.

NearbyViewDecor

4.99 out of 5 average rating, 169 reviews
Guest favourite
A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.
Home in Lee

Berkshire Vacation Home in Lee

Our spacious home is situated in a secluded neighborhood in Lee, MA (Berkshire County) and has 5 bedrooms & 2.5 baths. There is a fully equipped open concept kitchen/dining room and 2 living rooms with TVs and gas fireplaces. There is central air/heat, and a sun room that leads out to a deck overlooking our in-ground pool. Tanglewood, Antimony brewery, Balderdash winery, Hilltop Orchards, Laurel Lake, Highlawn Farm, outlets, golf, and Lenox & Stockbridge are all within a 20 minute drive.

NearbyOutdoor spacesBackyard

4.93 out of 5 average rating, 106 reviews
Guest favourite
A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.
Home in Canaan

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

NearbyOutdoor spacesBarbecue

4.91 out of 5 average rating, 187 reviews
Top Guest favourite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

ViewNearbyBathroom

5.0 out of 5 average rating, 119 reviews
Top Guest favourite
Apartment in North Adams

The MoCA-Cabana: 2 bd + Sauna

Welcome to the MoCA-Cabana at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just guest houses, Chase Hill is an experience: gardens, fire pits, sauna, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates often available beyond what the calendar shows—don’t hesitate to contact us!

NearbyOutdoor spacesBathroom

4.99 out of 5 average rating, 153 reviews
Guest favourite
An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.
Barn in East Chatham

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. A private outdoor sauna will be ready for all stays beginning October 1, 2026. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

NearbyOutdoor spacesBackyard

4.96 out of 5 average rating, 114 reviews
Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

ViewOutdoor spacesBarbecue

4.88 out of 5 average rating, 123 reviews
Top Guest favourite
A hammock is suspended between two large trees, offering a serene spot to relax by the water. Below, colorful kayaks rest on the grassy shore, framing the edge of Glass Lake, which reflects the surrounding greenery and blue sky.
Home in Averill Park

Lake House in Averill Park, NY

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Booking guest must be at least 25 years old.

ViewOutdoor spacesCleanliness

4.97 out of 5 average rating, 202 reviews
Guest favourite
Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

NearbyViewQuiet

4.94 out of 5 average rating, 135 reviews

Popular amenities for Pittsfield lake access rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Lake access house rentals

Top Guest favourite
The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.
Home in Otis

Idyllic family retreat - spacious lake home,

NearbyOutdoor spacesBackyard

4.95 out of 5 average rating, 175 reviews
Superhost
Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

Outdoor spacesViewCheck-in

4.89 out of 5 average rating, 152 reviews
Top Guest favourite
A bright and airy kitchen features a round wooden dining table surrounded by blue chairs. Natural light streams through large windows, illuminating the space and highlighting a vase of fresh flowers on the table. White cabinetry and light hardwood flooring create a cohesive, clean look.
Home in Monterey

Charming cottage w/ gorgeous views.

Outdoor spacesNearbyKitchen

4.93 out of 5 average rating, 373 reviews
Top Guest favourite
Home in Great Barrington

Modern Victorian- Walk to Town

Outdoor spacesNearbyKitchen

4.97 out of 5 average rating, 142 reviews
Top Guest favourite
The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.
Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Outdoor spacesNearbyLayout

4.99 out of 5 average rating, 120 reviews
Top Guest favourite
Home in Athens

Lake House close to Skiing & Indoor Hot Tub

Outdoor spacesNearbySleep quality

4.96 out of 5 average rating, 113 reviews
Guest favourite
A charming house is set within a wooded area, with autumn foliage creating a colorful backdrop. The exterior features a stone fireplace and expansive windows, offering glimpses of the serene environment. Nearby, a fire pit with seating is positioned on the green lawn.
Home in Becket

Beautiful, quiet and cozy home in Becket!

NearbyViewGetting around

4.93 out of 5 average rating, 159 reviews
Top Guest favourite
Home in Monterey

Beautiful family home, Hike, Fireplace, Sleeps 12

Outdoor spacesNearbyAccuracy

4.96 out of 5 average rating, 237 reviews

Lake access apartment rentals

Top Guest favourite
The exterior view of a spacious two-story home is presented, featuring a wraparound porch supported by white columns. Large windows illuminate the façade, while vibrant greenery from surrounding trees and gardens enhances the tranquil atmosphere.
Apartment in Great Barrington

Private En Suite in Beautiful Victorian

NearbyOutdoor spacesLong stay

4.95 out of 5 average rating, 429 reviews
Top Guest favourite
A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.
Apartment in Otis

Enjoy every season the Berkshires have to offer.

ViewOutdoor spacesBathroom

4.96 out of 5 average rating, 134 reviews
Top Guest favourite
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

Hudson River Beach House

NearbyOutdoor spacesLayout

4.99 out of 5 average rating, 168 reviews
Guest favourite
A welcoming living area is highlighted by natural light streaming in through large windows. A comfortable sectional sofa is paired with two patterned chairs and a round woven coffee table, creating an inviting space for relaxation. A television is positioned on an elegant media console.
Apartment in Craryville

Captain's Quarters at Mickey's Marina

ViewOutdoor spacesParks

4.91 out of 5 average rating, 179 reviews
Top Guest favourite
An open layout kitchen and living area is highlighted by exposed brick walls and hardwood flooring. A modern kitchen is equipped with stainless steel appliances, while a comfortable brown leather sofa is accompanied by a coffee table. Natural light enters through a window centered in the room.
Apartment in Hudson

Hip Warren Street Apartment

ViewNearbyHiking

5.0 out of 5 average rating, 124 reviews
Guest favourite
A cozy living area features a dark sofa adorned with colorful throw pillows. Natural light enters through a window, illuminating the space. A coffee table rests in front, complemented by a comfortable side chair and ottoman. Wall décor includes vintage items, enhancing the inviting atmosphere.
Apartment in Wilmington

Globetrotter Retreat - Minutes to the Mountain

Outdoor spacesViewCleanliness

4.89 out of 5 average rating, 339 reviews
Top Guest favourite
A well-lit sitting area features a cozy couch adorned with colorful cushions. A wooden coffee table sits in front of the couch, accompanied by a decorative bowl. Light wood flooring complements the beige and blue walls, while an entrance door is visible in the background.
Apartment in Clifton Park

A Place to Relax

NearbyQuietCleanliness

4.91 out of 5 average rating, 543 reviews
Top Guest favourite
A bright sunroom features large windows that allow natural light to illuminate the space. A gray and white patterned rug lies on the floor, complementing a cozy seating area with yellow cushions. A green dining table with chairs and potted plants add a touch of color.
Apartment in Great Barrington

Zen River Studio

ViewOutdoor spacesSleep quality

4.93 out of 5 average rating, 43 reviews

Lake access cottage rentals

Top Guest favourite
A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.
Cottage in Southwick

Lake Views from Deck Fire Pit & Hot Tub 4 Kayaks

Outdoor spacesViewDecor

4.98 out of 5 average rating, 168 reviews
Guest favourite
A tranquil outdoor scene showcases several wooden Adirondack chairs arranged around a fire pit, facing a calm body of water. The surrounding trees exhibit vibrant autumn colors, reflecting beautifully in the water, creating a serene natural atmosphere.
Cottage in Hudson

Hudson area waterfront-fish, kayak, farm visits!

NearbyViewAir conditioning

4.84 out of 5 average rating, 155 reviews
Top Guest favourite
An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.
Cottage in Livingston

Waterlily Lakehouse - Modern+Waterfront+Retreat

Outdoor spacesViewTV

4.97 out of 5 average rating, 147 reviews
Guest favourite
A spacious deck overlooks the lake, featuring a glass dining table surrounded by yellow chairs. A lounge chair is positioned nearby. A bright yellow umbrella provides shade, and trees frame the scene, accentuating the sunset sky in the background.
Cottage in Craryville

Oriole Cottage@Copake Lake: 4 Kayaks, 1 Canoe

ViewOutdoor spacesAmenities

4.82 out of 5 average rating, 136 reviews
Top Guest favourite
A modern living area is present, featuring a light-colored sofa accompanied by two side tables. A decorative lamp is positioned next to the sofa, enhancing the inviting ambiance. The open floor plan reveals a view of the kitchen in the background, creating a cohesive living space.
Cottage in Pittsfield

Charming Lakeview Cottage in the Berkshires

Outdoor spacesViewWalkability

5.0 out of 5 average rating, 16 reviews
Top Guest favourite
A waterside deck is shown, featuring a round table with a vase of flowers and several chairs. Relaxing seating options are visible, alongside a shaded area provided by a striped awning. The lake and distant mountains create a serene backdrop.
Cottage in Lanesborough

Pontoosuc Lakeshore

Outdoor spacesViewCheck-in

4.97 out of 5 average rating, 32 reviews
Guest favourite
Cottage in Pittsfield

Pine & Paddle | Pond Access • Kayaks

ViewNearbyPets

4.91 out of 5 average rating, 22 reviews
Guest favourite
Cottage in Otis

The lake house

NearbyViewParks

4.96 out of 5 average rating, 52 reviews

When is the best time to visit Pittsfield?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$321 AUD$292 AUD$269 AUD$456 AUD$491 AUD$463 AUD$285 AUD$347 AUD$296 AUD$369 AUD$282 AUD$491 AUD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

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