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Cottage holiday rentals in Western Massachusetts

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Top-rated cottage rentals in Western Massachusetts

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Top Guest favourite
A jetted swim spa is positioned on a deck overlooking Lake Garda at sunset. The water's surface reflects soft hues of orange and pink, with serene trees framing the view. The spa displays an illuminated edge, enhancing the tranquil atmosphere of the lakeside setting.
Cottage in Burlington
4.99 out of 5 average rating, 160 reviews

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

Top Guest favourite
A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 232 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top Guest favourite
Cottage in Becket
4.95 out of 5 average rating, 302 reviews

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. Approved pet = approved Pet Agreement.

Guest favourite
A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.
Cottage in Becket
4.9 out of 5 average rating, 124 reviews

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Top Guest favourite
A wooden rocking chair sits on a quaint porch, next to vibrant flower pots filled with blooming plants. Green grasses and a hint of autumn foliage create a serene outdoor setting, inviting relaxation and peaceful moments.
Cottage in New Lebanon
4.94 out of 5 average rating, 209 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

Guest favourite
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
4.93 out of 5 average rating, 258 reviews

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

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 (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • 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

Guest favourite
The exterior of a charming yellow cottage is visible, featuring dark green shutters and a welcoming porch with decorative elements. A well-kept garden with colorful flowers and greenery surrounds the cottage, while a gravel pathway leads to the entrance under a partly cloudy blue sky.
Cottage in Monroe
4.89 out of 5 average rating, 167 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Top Guest favourite
A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.
Cottage in Jamaica
4.84 out of 5 average rating, 593 reviews

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK

Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

Top Guest favourite
A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.
Cottage in Great Barrington
4.94 out of 5 average rating, 179 reviews

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Top Guest favourite
A charming blue cottage with a wooden fence is showcased, featuring an American flag mounted on the front. The entrance includes a door framed by two windows, and a rustic fence leads to the path, surrounded by autumn leaves and forest greenery.
Cottage in Williamstown
4.9 out of 5 average rating, 201 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs at $100 per dog. My cottage sits on 13 privately owned acres. Partially fenced in 3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Top Guest favourite
A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.
Cottage in Great Barrington
4.93 out of 5 average rating, 324 reviews

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

Guest favourite
A grill is positioned on the deck, with a serene view of Tully Pond at sunrise. The calm water reflects the warm colors of the sky, surrounded by trees and distant mountains.
Cottage in Orange
4.93 out of 5 average rating, 284 reviews

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a designed vacation home with breathtaking views of Tully Mountain. This 4-season Cottage has real salvaged barn wood walls; up-cycled maple floors and one-of-a kind scratch built furniture and lighting fixtures. The deconstructed architecture leaves exposed the electrical conduit and copper plumbing pipes, making the cottage feel alive and organic.

Popular amenities for Western Massachusetts cottage rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top Guest favourite
A charming single-story house is set against a partly cloudy sky. The exterior features light-colored siding and a welcoming front porch with steps leading up. A manicured lawn with green shrubbery surrounds the home, and a two-car garage is visible to the left.
Cottage in Kingston
4.94 out of 5 average rating, 64 reviews

Charming Cottage in Kingston - License #002740

Guest favourite
A spacious living area features a cozy leather sectional sofa adorned with decorative pillows. A round coffee table sits in front, and a dining table for four is visible nearby. Natural light filters through the window blinds, complemented by warm overhead lighting.
Cottage in Saratoga Springs
4.97 out of 5 average rating, 147 reviews

The King's Cottage- HOT TUB and Pet Friendly!

Guest favourite
A charming cottage is enveloped in fresh snow, with soft yellow lights glowing from its windows. The white exterior contrasts with the snow-covered landscape, while trees and bushes, dusted with snow, create a peaceful winter setting.
Cottage in Litchfield
4.87 out of 5 average rating, 391 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

Top Guest favourite
A cozy cottage is positioned amidst a lush field of wildflowers, with vibrant greenery surrounding it. The blue exterior of the cottage complements the clear blue sky and mountains in the background, creating a serene and inviting environment.
Cottage in Pownal
4.98 out of 5 average rating, 60 reviews

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem
4.99 out of 5 average rating, 142 reviews

Cozy Cottage |Quintessential CT | Pet Friendly

Guest favourite
A spacious family room features a vaulted ceiling with wooden beams. Seating includes a sectional sofa and two lounge chairs. A large smart TV is mounted above a minimalist fireplace. Natural light floods in from the expansive glass doors leading to a balcony.
Cottage in Wardsboro
4.97 out of 5 average rating, 100 reviews

Modern Cottage between Stratton and Mount Snow VT

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
4.99 out of 5 average rating, 141 reviews

Peaceful Snowy Lake Views from Private Hot Tub

Guest favourite
The jacuzzi hot tub is set on an outdoor deck, with water gently bubbling. Soft towels are neatly stacked nearby. In the background, a large tree provides shade, while vibrant foliage signals the transition of seasons in the surrounding landscape.
Cottage in Greenville
4.92 out of 5 average rating, 248 reviews

Historic farmhouse escape on 14 scenic acres

Pet-friendly cottage rentals

Top Guest favourite
A two-story lodge is nestled among tall trees, with a babbling brook flowing in the foreground. The exterior is a rich brown wood, complemented by green foliage and rocks near the water. A small balcony is visible on the second floor, enhancing the picturesque setting.
Cottage in Austerlitz
4.95 out of 5 average rating, 113 reviews

Harvey Mountain Lodge by State Forest

Top Guest favourite
A pass-through window features a wooden countertop, displaying decorative items and a candle. A vibrant blue refrigerator and various kitchen appliances are visible in the background. The space is brightened by natural light, creating a cheerful ambiance.
Cottage in Catskill
4.96 out of 5 average rating, 313 reviews

1930's Cottage charm fireplace, close to skiing

Superhost
An open living space features vibrant green walls and large windows that invite natural light. A comfortable couch and a wooden coffee table are positioned on polished hardwood flooring. In the back, a dining area with a wooden bar and chairs is visible, offering views of the surrounding greenery.
Cottage in Catskill
4.93 out of 5 average rating, 136 reviews

Evergreen Escape - Woodsy Artistic Retreat

Top Guest favourite
A cozy living space features a modern gas fireplace centrally placed against a white brick wall. Two stylish chairs with black woven seats are positioned beside the fireplace, while a natural wood table adds warmth. A patterned rug enhances the inviting atmosphere of the room.
Cottage in Red Hook
4.99 out of 5 average rating, 102 reviews

Creekside Cottage | The Fitz House Red Hook NY

Guest favourite
A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.
Cottage in Rhinebeck
4.93 out of 5 average rating, 327 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Guest favourite
A modern black cottage is presented, set against a backdrop of tall trees and natural stone landscaping. A gravel driveway leads up to the entrance, where steps ascend to a covered porch. A dog is seen on the grassy area nearby.
Cottage in Cornwall
4.92 out of 5 average rating, 187 reviews

Newly Built Cottage in Housatonic Valley

Guest favourite
An open living area features a dining table surrounded by wooden chairs. A comfortable sofa sits near a coffee table, with an air conditioning unit and a television mounted on the wall. Wooden beams adorn the ceiling, contributing to a cozy atmosphere.
Cottage in Bernardston
4.87 out of 5 average rating, 344 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Guest favourite
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
4.85 out of 5 average rating, 290 reviews

Wildlife Lakeside Cottage; views/wildlife

Private cottage rentals

Top Guest favourite
A charming wooden house is surrounded by a snowy landscape, showcasing a large deck and steps leading to the entrance. Snow-covered trees and a clear blue sky enhance the serene setting. The structure features multiple levels, presenting a cozy, inviting exterior.
Cottage in Newfane
4.91 out of 5 average rating, 277 reviews

Ridgeview: Cozy Cottage with a View

Top Guest favourite
The image showcases a peaceful lakeside setting with a cottage and a screened gazebo near the water. The area features lush trees and a well-maintained lawn leading to the private beach area on the lake. A clear blue sky is visible overhead.
Cottage in Killingly
4.94 out of 5 average rating, 463 reviews

Lake front cottage

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
4.99 out of 5 average rating, 164 reviews

Cozy Cottage in the Berkshires

Guest favourite
A serene lakefront home is nestled among tall trees, featuring a welcoming porch that overlooks the water. The exterior is painted in soft yellow, set against a backdrop of lush greenery. Nearby structures showcase a variety of architectural styles along the lakeshore.
Cottage in Shutesbury
4.92 out of 5 average rating, 237 reviews

Lake Wyola House Shutesbury Massachusetts

Top Guest favourite
A charming small home is presented, featuring a welcoming front porch with steps leading to the entrance. Lush green grass surrounds the house, accentuated by colorful flowering shrubs. Tall trees provide shade, while a gravel driveway provides access to parking.
Cottage in Williamstown
4.99 out of 5 average rating, 128 reviews

Charming Williamstown Cottage

Guest favourite
The exterior of the Little Yellow Cottage features a charming yellow facade with white trim. A round window and a cupola add character to the roof. Surrounding greenery provides a natural setting, while a small white statue of a goat sits in front of the entrance steps.
Cottage in Highland
4.89 out of 5 average rating, 678 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Top Guest favourite
Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.
Cottage in Newfane
4.99 out of 5 average rating, 269 reviews

Cozy Vermont Antique Sugar House with Fireplace

Top Guest favourite
A living area features hardwood floors and a cozy ambiance. A vintage-style cabinet holds a television, while a lamp softly illuminates a decorative wall art piece. A comfortable chair is positioned nearby, with a large open shelving unit displaying books and decorative items.
Cottage in Amherst
4.93 out of 5 average rating, 177 reviews

Beautifully Restored Cottage Studio

Destinations to explore