Pet-friendly holiday rentals in Lenox

4.97 out of 5 average rating, 101 reviews

An inviting living space features a blue sofa adorned with colorful cushions, complemented by an orange wall. Framed artwork is displayed prominently, with a stylish hat resting on a black basket. A doorway leads to additional rooms, enhancing the room's spacious feel.

Home in Becket

Nerd Preservation Sanctuary

Nerdscapist, geekmantic country home; perfect for oddballs who wish for a crafty, private, hilarious country retreat. Featuring a bad art print collection from the glorious MA Museum of Bad Art (Or Mass MOBA). Original bad art and sculpture. Much scope for the imagination's doofiest crevices. Redonkulously close to all the local fun: tiny drive to 5 lakes, Jacob's Pillow, Tanglewood 17 mi, Otis ski, 1/2 hr to Butternut Ski & Tubing Pittsfield & Great Barrington, hour to Berkshire E & Mass MOCA.

4.94 out of 5 average rating, 119 reviews

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?!

4.91 out of 5 average rating, 360 reviews

A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.

Flat in Copake Falls

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

4.95 out of 5 average rating, 159 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!

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.

Guest house in Cummington

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.

5 out of 5 average rating, 162 reviews

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!

4.87 out of 5 average rating, 128 reviews

The spacious bedroom features a plush king-sized bed with high-end linens. A large rug covers the wooden floor, while accented walls create a modern atmosphere. A doorway leads to a bathroom, and additional furniture includes two gold-framed chairs and a desk beside a window.

Flat in Great Barrington

King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

4.93 out of 5 average rating, 241 reviews

Lush, colorful flowers surround the entrance of the cottage, adding a vibrant touch to the exterior. A combination of greenery and blooms creates a welcoming atmosphere. The cottage features large windows, allowing for ample natural light and offering views of the blooming landscape.

Home in Lenox

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

Guest house in Housatonic

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.

4.96 out of 5 average rating, 156 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.

4.89 out of 5 average rating, 209 reviews

A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.

Flat in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

4.76 out of 5 average rating, 145 reviews

A spacious living area features light-colored walls and wooden flooring. A gray sectional sofa is positioned beside two white armchairs, with accent pillows enhancing comfort. A coffee table sits at the center, surrounded by a vibrant area rug. Natural light is provided by windows with simple treatments.

Guest suite in Lee

Cozy Guesthouse Near Downtown, Lee

Welcome and enjoy our renovated Guesthouse at Lee, MA, staying on main street (15 minutes from Great Barrington and 20 minutes from Pittsfield). It is also 3 mins to Outlet and 19 mins to the closest Ski area.The master bedroom has a queen size soft mattress, and the second bedroom has a queen bed also. The kitchen has a brand new refrigerator, a gas range, and units for cooking. You will enjoy the comfortable stay! Owners live upstairs and be friendly to all visits.

4.89 out of 5 average rating, 111 reviews

A welcoming living area features exposed brick walls and a patterned area rug. A vintage-style couch is placed in front of a wooden coffee table. A curtain separates the sleeping area, which is partially visible in the background, revealing a cozy bed.

Flat in Troy

Cool Brick Basement Studio Parking Fast WiFi AC

Cool 1900 brick basement level studio with curtained off sleeping area, fast wifi, tile floors, brick walls, nearly new kitchen, granite countertops, air conditioning & shared laundry. South Central Troy (Washington Park Neighborhood) quiet street, just 1 block to Carmen's Cafe, 3 blocks to Russell Sage, within walking distance to quaint shops, dining, nightlife and everything else Downtown Troy has to offer. Close to R.P.I, H.V.C.C, and Emma Willard.

4.98 out of 5 average rating, 138 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

7 MINUTES TO BOUSQUET MOUNTAIN Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens, unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Popular amenities for Lenox pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 115 reviews

A two-story historic home is showcased with blue siding and white trim. The front porch features a railing and is lined with flower beds. Windows are adorned with dark frames, and an air conditioning unit is visible. A driveway leads to a parked vehicle on the side.

Home in Athens

Renovated historic home, walk to Hudson River!

4.86 out of 5 average rating, 147 reviews

A rustic kitchen space features a large dining table surrounded by green chairs, with a centerpiece of fresh greenery. Exposed wooden beams and stone walls enhance the charm. A vintage stove and additional cooking essentials are visible, along with warm lighting from hanging fixtures.

Home in Hudson

19th Century Mill House with River View

4.96 out of 5 average rating, 215 reviews

A tranquil lake scene is presented, with calm waters reflecting greenery from the surrounding trees. A wooden dock extends into the lake, while a selection of houses is visible in the distance, nestled among the landscape.

Home in Copake

Lakefront +pets +skiing +bbq +firepit +games

4.98 out of 5 average rating, 173 reviews

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

Home in Saugerties

The Stone House

4.96 out of 5 average rating, 114 reviews

Home in Hudson

Stylish Pet-Friendly Retreat w/ Hot Tub

4.7 out of 5 average rating, 125 reviews

The exterior of a two-story yellow house is presented, featuring a front porch with large windows and a central door. A water tower is visible in the background, surrounded by greenery and a gravel pathway leading to the entrance.

Home in Housatonic

Relaxing Housatonic Retreat

4.97 out of 5 average rating, 197 reviews

The exterior of the house is framed by lush greenery, featuring a wooden pathway leading to the entrance. Potted plants with purple flowers adorn the area, and a decorative wind chime hangs in a circular frame, enhancing the natural setting.

Home in Catskill

Modern Prefabricated Architectural Retreat

4.96 out of 5 average rating, 187 reviews

An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.

Home in Great Barrington

Elegant Year-Round Lakeside Retreat with AC

Pet-friendly home rentals with a pool

4.89 out of 5 average rating, 182 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

5 out of 5 average rating, 102 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.

4.94 out of 5 average rating, 157 reviews

A charming dining area is highlighted by a rustic wooden table accompanied by black chairs. Natural light enters through multiple windows, illuminating the space. A brick fireplace serves as a focal point, decorated with potted plants and nautical-themed decor.

Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

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, 118 reviews

Cozy Cottage with pool and walk to lake

Guest house in Stanfordville

A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.

4.93 out of 5 average rating, 190 reviews

Eco Cottage in the Woods

4.96 out of 5 average rating, 377 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

5 out of 5 average rating, 161 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

4.96 out of 5 average rating, 121 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.

Flat in Otis

Enjoy every season the Berkshires have to offer.

Private, pet-friendly home rentals

4.91 out of 5 average rating, 11 reviews

Cottage in Pittsfield

Chic Cottage at Richmond Pond

4.89 out of 5 average rating, 114 reviews

The charming cabin features a spacious front porch with wooden rocking chairs and decorative string lights. A well-maintained yard surrounds the structure, with green grass and flowering plants. The cabin's wood exterior blends harmoniously with the natural landscape of trees and open sky.

Cabin in Catskill

Cozy Cabin w/ 10 Min Walk to Downtown Catskill

4.97 out of 5 average rating, 39 reviews

The bright living room features a mix of comfortable seating options, including an armchair and a sectional sofa, arranged around a circular coffee table. Natural light filters through large windows, enhancing the inviting atmosphere. A TV is positioned on an adjacent stand, with a door leading outside.

Home in Lenox Dale

Sun Filled Lenox Retreat - Minutes to Tanglewood!

5 out of 5 average rating, 4 reviews

Home in Lee

Modern & Stylish Berkshires Home

4.96 out of 5 average rating, 136 reviews

The spacious studio apartment features a well-equipped kitchen with a countertop and bar seating. Natural light filters through the windows, highlighting wooden cabinetry and modern appliances. The open layout includes a cozy seating area, creating a functional living space beneath sloped ceilings.

Flat in Williamsburg

The cozy clubhouse

4.85 out of 5 average rating, 34 reviews

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 Winter Chalet I Close to Ski & Downtown Lenox

4.94 out of 5 average rating, 212 reviews

A well-lit studio space features a spacious bed dressed in white linens with decorative pillows. Light wooden cabinets and a dining table with four chairs are visible in the background, complemented by a full kitchen equipped with essential appliances.

Guest suite in Hudson

Harmony Valley Home, bright & inviting studio