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Pet-friendly vacation rentals in Lenox

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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 $271 CAD 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 and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Lenox vacation rentals include wifi 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 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.

4.95 out of 5 average rating, 323 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!

4.97 out of 5 average rating, 112 reviews
Guest favourite
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

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

4.93 out of 5 average rating, 139 reviews
Guest favourite
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

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.

4.95 out of 5 average rating, 193 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 Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. 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. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

4.96 out of 5 average rating, 114 reviews
Guest favourite
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

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!

4.97 out of 5 average rating, 157 reviews
Guest favourite
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

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more! Find us on social media: @stonebridgecabin

4.88 out of 5 average rating, 109 reviews
Guest favourite
Guesthouse in Great Barrington

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.

4.95 out of 5 average rating, 180 reviews
Guest favourite
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

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*

4.91 out of 5 average rating, 175 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.

5.0 out of 5 average rating, 120 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 -Naumkeag Pumpkin Show/Christmas Lights -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

4.93 out of 5 average rating, 138 reviews
Guest favourite
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.

4.95 out of 5 average rating, 155 reviews

Popular amenities for Lenox pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
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

Dancing Horse Lodge

4.87 out of 5 average rating, 332 reviews
Superhost
A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.
Home in Hudson

Bright, Airy Home in Hudson w/ TONS of Character!

4.82 out of 5 average rating, 310 reviews
Guest favourite
Home in Chatham

Chatham on the Creek. Pet friendly. F Trump

4.91 out of 5 average rating, 297 reviews
Top guest favourite
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

The old sawmill from 1771

4.99 out of 5 average rating, 389 reviews
Top guest favourite
An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.
Home in Dalton

Brooksong, the perfect Berkshires getaway

4.93 out of 5 average rating, 214 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!

4.93 out of 5 average rating, 159 reviews
Superhost
Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

4.87 out of 5 average rating, 154 reviews
Guest favourite
A charming red house is set against a backdrop of lush greenery. The stone chimney adds a rustic touch, while outdoor seating is arranged on the lawn. A small tower feature enhances the unique architectural design, creating an inviting outdoor space.
Home in Great Barrington

Never too early to book for the Holidays & NYE!

4.91 out of 5 average rating, 144 reviews

Pet-friendly home rentals with a pool

Guest favourite
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

Berkshire Getaway Ranch 3 acres + saltwater pool

4.93 out of 5 average rating, 111 reviews
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.

4.96 out of 5 average rating, 136 reviews
Top guest favourite
A serene view features a private in-ground pool surrounded by lounge chairs, each shaded by black umbrellas. Lush green trees border the backyard, and a red house is visible in the background, completing the outdoor vacation atmosphere.
Home in Canaan

Berkshire Lake House, gunite pool, Chef's Kitchen

4.99 out of 5 average rating, 102 reviews
Top guest favourite
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

4.95 out of 5 average rating, 172 reviews
Top guest favourite
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

Hudson River estate guest cottage

4.98 out of 5 average rating, 109 reviews
Top guest favourite
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

4.98 out of 5 average rating, 136 reviews
Top guest favourite
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.

5.0 out of 5 average rating, 114 reviews
Top guest favourite
A spacious hot tub is positioned under a wooden pavilion, surrounded by string lights. Water cascades gently inside, with soft lighting reflecting on the surface. In the background, a tranquil view of the lake and nearby seating areas can be seen, inviting relaxation.
Home in Athens

Hudson Valley Lake · Hot Tub · Dock · Games · View

4.98 out of 5 average rating, 113 reviews

Private, pet-friendly home rentals

Top guest favourite
The rustic carriage house is surrounded by lush greenery, featuring a vibrant garden with various plants and flowers. A teal umbrella provides shade over an outdoor seating area, complemented by a stone pathway leading to the entrance, enhancing the inviting atmosphere of the setting.
Cottage in Great Barrington

Carriage house with Chef's Kitchen, close to town

4.93 out of 5 average rating, 163 reviews
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

Harvey Mountain Lodge by State Forest

4.93 out of 5 average rating, 130 reviews
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

Wildlife Lakeside Cottage; views/wildlife

4.85 out of 5 average rating, 301 reviews
Top guest favourite
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

Swiss Chalet Style Timberframe Home in Berkshires

4.93 out of 5 average rating, 311 reviews
Top guest favourite
A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.
Cabin in Plainfield

Peaceful Cabin in the Woods

4.92 out of 5 average rating, 261 reviews
Superhost
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

Cozy Chalet Near Downtown Lenox, Foliage Beauty

4.87 out of 5 average rating, 46 reviews
Guest favourite
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

Spacious Central Berkshires Home for Groups

4.9 out of 5 average rating, 58 reviews
Top guest favourite
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

4.95 out of 5 average rating, 21 reviews

When is the best time to visit Lenox?

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Avg. price$351 CAD$326 CAD$336 CAD$338 CAD$393 CAD$423 CAD$433 CAD$389 CAD$279 CAD$321 CAD$282 CAD$419 CAD
Avg. temp-5 °C-4 °C1 °C8 °C14 °C18 °C21 °C20 °C16 °C9 °C4 °C-2 °C

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