Pet-friendly vacation rentals in Becket

4.95 out of 5 average rating, 320 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, 110 reviews

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!

4.99 out of 5 average rating, 222 reviews

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!

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.

4.93 out of 5 average rating, 159 reviews

Beautiful, quiet and cozy home in Becket!

If you are looking for a peaceful and relaxing getaway, then this is the place for you! Our cozy house in the Berkshires is ready to invite you to surround yourself with nature and see its beauty. Our home has 2 bedrooms and 1 bath, but has enough room to sleep up to 6 guests. There is also a living room, stocked kitchen and a room with a sleep sofa. Feel free to enjoy the wood burning electric fire place, the back deck, grill and fire pit outside. Pets are welcome! Book your stay & enjoy!

4.88 out of 5 average rating, 108 reviews

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

4.97 out of 5 average rating, 498 reviews

A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.

Apartment in Northampton

Light filled three bedroom apartment DT Florence!

Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

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.

5.0 out of 5 average rating, 119 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.

Treehouse in New Marlborough

The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

4.91 out of 5 average rating, 181 reviews

4.96 out of 5 average rating, 134 reviews

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.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

4.96 out of 5 average rating, 237 reviews

Home in Monterey

Beautiful family home, Hike, Fireplace, Sleeps 12

Voted by Airbnb guests as a top "Wish-listed family home" * A beautiful 5 bedroom post & beam house in the woods off the Appalachian trail. * Butternut ski Mountain 15 mins * Roaring fireplace & free firewood * Outdoor fire pit * Great Hikes from the house * Pets welcome * Fast Wifi - Fiber * Great Barrington 15 mins/ local shops * Kids activities at the house & area. * Jacobs Pillow & Tanglewood 20 mins * Fishing, kayaking & Swimming Lake 5 mins

4.97 out of 5 average rating, 310 reviews

The exterior of a renovated farmhouse is surrounded by lush greenery and flowering shrubs. A stone pathway leads to the front porch, which features a pair of chairs. A barn is visible in the background, set against a backdrop of trees and hills.

Home in Russell

South Quarter House

Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)

4.94 out of 5 average rating, 135 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 Becket pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.97 out of 5 average rating, 118 reviews

Home in Lenox

Restored 1881 Farm House

4.95 out of 5 average rating, 191 reviews

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!

4.93 out of 5 average rating, 212 reviews

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

4.86 out of 5 average rating, 104 reviews

Aerial view of Lake Garfield, with smooth waters reflecting the surrounding greenery. Two kayaks are visible, gliding across the lake near a small motorboat. Lush trees line the shoreline, with a private dock and patio area partially seen along the bank.

Home in Monterey

Forest Hollow | Waterfront • Kayaks • Wood Stove

4.99 out of 5 average rating, 252 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

4.97 out of 5 average rating, 143 reviews

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

Stylish Mid-century Modern Berkshires Cape

4.99 out of 5 average rating, 387 reviews

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

4.97 out of 5 average rating, 157 reviews

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

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 585 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

Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

4.97 out of 5 average rating, 185 reviews

4.88 out of 5 average rating, 222 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

4.98 out of 5 average rating, 135 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

4.95 out of 5 average rating, 171 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

5.0 out of 5 average rating, 114 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.

4.96 out of 5 average rating, 398 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

4.98 out of 5 average rating, 109 reviews

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

Private, pet-friendly home rentals

4.92 out of 5 average rating, 258 reviews

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

4.95 out of 5 average rating, 130 reviews

Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

Tiny home in New Marlborough

Bedroom Forest View I Sauna I Fire-pit I Trails

4.94 out of 5 average rating, 201 reviews

Apartment in Great Barrington

A modern bedroom is presented, featuring a plush king-sized bed with crisp white linens. A sliding glass door allows access to an outdoor space, while a small table and decorative items add to the aesthetic. A dark accent wall provides depth, complemented by natural light.

King Bed |Wi-Fi| 2m to Ski Resort

4.92 out of 5 average rating, 223 reviews

4.96 out of 5 average rating, 114 reviews

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

Guesthouse in Great Barrington

Sweet Victorian in Housatonic

4.95 out of 5 average rating, 177 reviews

A rustic chalet is situated among lush greenery, overlooking a peaceful lake. A wooden dock extends into the water, with tall grasses framing the shoreline. The home is partially visible, surrounded by trees and natural landscape.

4.93 out of 5 average rating, 84 reviews

Little Longbow Lakefront Chalet