Pet-friendly vacation rentals in Lenox

4.95 out of 5 average rating, 309 reviews

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.

4.97 out of 5 average rating, 156 reviews

An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.

Cabin in Saugerties

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

5 out of 5 average rating, 200 reviews

A cozy sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.

Guesthouse in Cummington

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

4.95 out of 5 average rating, 246 reviews

A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.

Home in Catskill

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

4.93 out of 5 average rating, 198 reviews

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

Berkshires/Pet Friendly/Tanglewood/Private Ranch

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail Rides /Horse activities available by appt!

4.95 out of 5 average rating, 485 reviews

A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.

Home in Germantown

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

4.98 out of 5 average rating, 175 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

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.

5 out of 5 average rating, 102 reviews

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.

4.99 out of 5 average rating, 160 reviews

A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.

Cabin in Round Top

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Tiny home in New Marlborough

4.94 out of 5 average rating, 168 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

4.95 out of 5 average rating, 144 reviews

The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.

Apartment in Lenox

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

4.96 out of 5 average rating, 114 reviews

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

Popular amenities for Lenox pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 114 reviews

Nerd Preservation Sanctuary

4.98 out of 5 average rating, 127 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

4.98 out of 5 average rating, 129 reviews

The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.

Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

4.99 out of 5 average rating, 123 reviews

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

Home in Great Barrington

Private Home in The Berkshires (New Hot Tub!)

4.87 out of 5 average rating, 135 reviews

A bright living room features a blue sectional sofa adorned with a mustard-colored throw pillow. A wooden coffee table is set in front, with a patterned rug beneath. Large windows invite natural light, while artworks and plants contribute to the welcoming space.

Home in Amenia

The Wheelhaus—Restored Home in Hamlet of Amenia

Superhost

A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.

Home in Cheshire

4.86 out of 5 average rating, 225 reviews

19th c. Barn in The Berkshires

4.86 out of 5 average rating, 108 reviews

A charming exterior view of the home shows a modest structure with a gray shingle facade and green windows. A wooden deck extends toward a seating area, while a pathway of stepping stones leads through the yard. Lush greenery is visible in the background.

Home in Clarksburg

New & Cozy~Near MoCa~Deck~River

4.93 out of 5 average rating, 106 reviews

Lakeside Retreat | Dock, Kayaks & Fire Pit

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 165 reviews

A modern tiny house is surrounded by the serene landscape of Columbia County. Bare trees and evergreen shrubs frame the structure, while the soft grass adds a natural touch. Large windows allow natural light to illuminate the interior, enhancing the connection to the outdoors.

Tiny home in Ghent

Country Getaway Tiny House in woods w/Pool/Sauna

4.93 out of 5 average rating, 569 reviews

A charming property is illuminated with colorful lights during the evening. The spacious deck is adorned with festive decorations, and a Christmas tree can be seen through large windows. The surrounding area is dark, emphasizing the warm glow of the lights.

Bungalow in Easthampton

The Creation Station

4.84 out of 5 average rating, 120 reviews

Apartment in Burlington

Charming apartment with breathtaking view!

5 out of 5 average rating, 105 reviews

A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.

Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

4.89 out of 5 average rating, 203 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

Cottage in West Sand Lake

The living area features a green couch and a wooden coffee table, complemented by a comfortable rocking chair. A flat-screen TV is positioned on a media console. Natural light filters through large windows framed by sheer curtains, illuminating the vaulted knotty pine ceiling.

4.99 out of 5 average rating, 119 reviews

Cozy Cottage with pool and walk to lake

4.94 out of 5 average rating, 161 reviews

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

4.96 out of 5 average rating, 380 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

Private, pet-friendly home rentals

4.96 out of 5 average rating, 24 reviews

A wooden cabin nestled among green trees showcases a welcoming entrance with steps leading up to a spacious deck. Natural light fills the facade, accentuating the structure's earthy tones and inviting presence amidst the surrounding forest.

Cabin in Spencertown

Wake Up in the Woods, A Summer Reset Upstate

5 out of 5 average rating, 13 reviews

The exterior of the cottage features light grey siding and a charming front door adorned with seasonal wreaths. Large windows invite natural light, while the surrounding snow-covered landscape highlights the tranquility of the setting. A garage is visible on the side of the property.

Home in Lenox

The Lenox Cottage

5 out of 5 average rating, 6 reviews

Home in Lee

Stylish Berkshires Retreat

5 out of 5 average rating, 56 reviews

An outdoor area features a wooden barrel sauna alongside a modern hot tub. The hot tub's white surface contrasts with the natural wood of the sauna, set against a backdrop of lush green trees and a wooden fence, creating a serene environment for relaxation.

Home in Great Barrington

Sauna + Hot Tub Escape | Private & Pet Friendly

5 out of 5 average rating, 51 reviews

Two eco homes are situated in a tranquil forest setting, softly illuminated by warm exterior lights at dusk. Wooden decks extend from the homes, providing a connection to the surrounding green space. Trees frame the scene, enhancing the natural ambiance.

Cabin in Ancram

2bed farm stay as seen in Dezeen, architects cabin

Superhost

Cabin in Lenox

5 out of 5 average rating, 3 reviews

Timpani Corners | Private Pond • AC

4.96 out of 5 average rating, 56 reviews

A wooden Adirondack chair is positioned in a shadowy corner of a cabin, overlooking an expansive view of rolling hills adorned in autumn foliage. Bright oranges and yellows frame the distant mountains under a clear blue sky.

Cabin in Becket

Entire Private Log Cabin in the Berkshires