Pet-friendly vacation rentals in Pittsfield

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Top-rated pet-friendly home rentals in Pittsfield

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

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Guest favorite

Home in Canaan

5.0 out of 5 average rating, 134 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Feb 18 – 25

R2,858 ZAR per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 236 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

May 8 – 15

R2,322 ZAR per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 260 reviews

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!

Oct 11 – 18

R1,876 ZAR per night

Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 274 reviews

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Jan 31 – Feb 7

R2,241 ZAR per night

Guest favorite

Home in Dalton

4.92 out of 5 average rating, 171 reviews

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

Sep 29 – Oct 6

R6,747 ZAR per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 264 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Apr 20 – 27

R2,602 ZAR per night

Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 102 reviews

Hidden Oasis in the Mountains by Evergreen Home

Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens & sip coffee as you watch the sunrise over the mountains from the screened-in porch. 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.

Dec 28 – Jan 4

R11,793 ZAR per night

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

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(will consider pets.)(90 second walk through wooded path to lake)

Feb 23 – Mar 2

R3,506 ZAR per night

Guest favorite

Apartment in Northampton

4.95 out of 5 average rating, 281 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Modern cozy 1BR with living space, private bathroom, private driveway, screened porch, coded door, and inflatable hot tub! Wooded neighborhood. Bike path along river. 5 min. drive to Look Park. 10 min. drive to Northampton. BR has luxury queen bed, single bed, AC. Cozy LR, WiFi, 55" TV, equipped kitchen. Near excellent hikes. A family lives in attached unit so there is some noise, not during sleep hours. Cats have lived here in the past. Great getaway spot!

Sep 18 – 25

R1,897 ZAR per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 284 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 6 – 13

R2,690 ZAR per night

Guest favorite

Guest suite in Austerlitz

4.86 out of 5 average rating, 138 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Apr 21 – 28

R1,536 ZAR per night

Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 154 reviews

Dog Friendly Farm Spring bird watching

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Sep 13 – 20

R2,967 ZAR per night