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Pet-friendly vacation rentals in Lenox

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Lenox

  • Total vacation rentals

    Explore 50 vacation rentals in Lenox

  • Nightly prices starting at

    Lenox vacation rentals start at $190 per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Lenox vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lenox rentals

  • 4.9 Average rating

    Lenox stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Lenox

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in East Nassau
4.97 out of 5 average rating, 107 reviews

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!

Outdoor spacesPetsBackyard

Top guest favorite
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
4.95 out of 5 average rating, 320 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. $29. pet fee = approved Pet Agreement.

WalkabilityOutdoor spacesHiking

Guest favorite
An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.
Home in Stockbridge
4.95 out of 5 average rating, 188 reviews

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

WalkabilityPetsBathroom

Guest favorite
A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.
Home in Pittsfield
4.97 out of 5 average rating, 157 reviews

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

Outdoor spacesPetsLaundry

Guest favorite
A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.
Guesthouse in Great Barrington
4.95 out of 5 average rating, 174 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

PetsWalkabilityAccuracy

Guest favorite
A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.
Guesthouse in Stockbridge
4.91 out of 5 average rating, 174 reviews

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

WalkabilityPetsLaundry

Top guest favorite
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
5.0 out of 5 average rating, 116 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.

Outdoor spacesWalkabilityGetting around

Guest favorite
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
4.96 out of 5 average rating, 112 reviews

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.

PetsOutdoor spacesIndoor spaces

Guest favorite
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
4.95 out of 5 average rating, 152 reviews

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.

PetsWalkabilitySkiing

Guest favorite
Home in Becket
4.94 out of 5 average rating, 134 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

PetsWalkabilityCheck-in

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
4.92 out of 5 average rating, 145 reviews

Comfy cabin with scenic 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!

WalkabilityOutdoor spacesParks

Top guest favorite
A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.
Home in Lee
4.97 out of 5 average rating, 141 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

PetsOutdoor spacesHeating

Popular amenities for Lenox pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favorite
A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.
Home in Pittsfield
4.87 out of 5 average rating, 330 reviews

Dancing Horse Lodge

PetsWalkabilityIndoor spaces

Guest favorite
A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.
Home in Lee
4.88 out of 5 average rating, 108 reviews

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Outdoor spacesPetsAccuracy

Guest favorite
An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.
Home in Pittsfield
4.93 out of 5 average rating, 134 reviews

Net Zero home with rustic Berkshire charm

Outdoor spacesWalkabilitySkiing

Superhost
Home in Hudson
4.91 out of 5 average rating, 149 reviews

Designer Home, Hot Tub, Private Yard, & Projector

Outdoor spacesWalkabilityCheckout

Guest favorite
A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.
Home in Stockbridge
4.89 out of 5 average rating, 126 reviews

Rabbit Run in the heart of Stockbridge Village

WalkabilityPetsGrill

Top guest favorite
A charming two-story red house is surrounded by lush greenery and colorful flowering plants. Sturdy steps lead up to the entrance, framed by vibrant shrubs and hydrangeas, creating a welcoming outdoor area that blends naturally with the landscape.
Home in New Lebanon
4.99 out of 5 average rating, 386 reviews

The old sawmill from 1771

WalkabilityOutdoor spacesView

Top guest favorite
A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.
Home in Catskill
4.97 out of 5 average rating, 231 reviews

Cheerful Catskill Village Cottage

WalkabilityOutdoor spacesParking

Guest favorite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield
4.93 out of 5 average rating, 108 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

PetsOutdoor spacesFamily

Pet-friendly home rentals with a pool

Top guest favorite
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
4.95 out of 5 average rating, 170 reviews

Cozy cottage with pool, walking distance to lake

WalkabilityPetsHospitality

Top guest favorite
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
4.98 out of 5 average rating, 134 reviews

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Outdoor spacesPetsCondition

Top guest favorite
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
4.96 out of 5 average rating, 133 reviews

Enjoy every season the Berkshires have to offer.

WalkabilityPetsBiking

Top guest favorite
A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.
Home in Coxsackie
4.98 out of 5 average rating, 108 reviews

Hudson River estate guest cottage

Outdoor spacesPetsGetting around

Top guest favorite
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
5.0 out of 5 average rating, 111 reviews

The Copake Cabin - A rustic-modern retreat.

PetsOutdoor spacesCheckout

Top guest favorite
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
4.96 out of 5 average rating, 396 reviews

Modern Upstate Cabin, near Rhinebeck NY

Outdoor spacesPetsParks

Top guest favorite
A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.
Home in Williamstown
4.9 out of 5 average rating, 239 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Outdoor spacesPetsAir conditioning

Top guest favorite
Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.
Home in Athens
4.95 out of 5 average rating, 194 reviews

Private lakefront home, hot tub & resort amenities

PetsOutdoor spacesLaundry

Private, pet-friendly home rentals

Guest favorite
A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.
Apartment in Stockbridge
4.92 out of 5 average rating, 102 reviews

Stockbridge private apartment

PetsOutdoor spacesQuiet

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
4.85 out of 5 average rating, 300 reviews

Wildlife Lakeside Cottage; views/wildlife

WalkabilityOutdoor spacesBackyard

Top guest favorite
Guesthouse in North Adams
5.0 out of 5 average rating, 336 reviews

Netherwood - North Adams Guest House with Views

Outdoor spacesWalkabilityAmenities

Top guest favorite
A chalet-style home is situated on a forested property, with a spacious deck extending from the front. Large windows reflect the surrounding greenery, showcasing a modern aesthetic against a backdrop of autumn foliage. Rock formations and scattered leaves cover the ground.
Chalet in Peru
4.93 out of 5 average rating, 311 reviews

Swiss Chalet Style Timberframe Home in Berkshires

Outdoor spacesWalkabilityBackyard

Top guest favorite
Guesthouse in Cummington
4.99 out of 5 average rating, 221 reviews

Cozy Hilltown Cottage

Outdoor spacesWalkabilityIndoor spaces

Guest favorite
The cabin is nestled in a wooded area, surrounded by lush greenery. A large deck extends from the front of the home, with firewood stacked neatly beside it. The architecture features an A-frame design, blending harmoniously with the natural landscape.
Chalet in Lenox
4.87 out of 5 average rating, 46 reviews

Modern Chalet Near Tanglewood & Downtown Lenox

WalkabilityOutdoor spacesHospitality

Guest favorite
A bright living room features a comfortable white sofa and a plush armchair beside a coffee table on a patterned rug. Large windows allow natural light to illuminate the space, while a television is positioned against a wooden accent wall. A potted plant adds a touch of greenery.
Home in Lee
4.89 out of 5 average rating, 54 reviews

Spacious Central Berkshires Home for Groups

Outdoor spacesWalkabilityDecor

Top guest favorite
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
4.95 out of 5 average rating, 20 reviews

The Lenox Cottage

WalkabilityPetsSleep quality

When is the best time to visit Lenox?

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Avg. price$246$229$236$237$276$297$304$273$196$225$198$294
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