Pet-friendly holiday rentals in Great Barrington

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Great Barrington

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Superhost

Cottage in Averill Park

4.94 out of 5 average rating, 138 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Superhost

Home in Saugerties

4.87 out of 5 average rating, 127 reviews

Le Petit Cottage - French Country in Saugerties

Le Petit Cottage is a cozy renovated farmhouse retreat in the heart of the scenic Hudson Valley, located 2 hours from NYC, Saugerties, NY Set on a spacious corner lot across from a waterfall, the house has gorgeous mountain views, with 3 bedrooms and 2 baths, and comfortably sleeps 6 people. The house features a high-end kitchen, a wood-burning stove, and luxurious amenities. This property is extremely dog-friendly! Centrally located to Woodstock, Kingston, and under 25 minutes to Hunter Mtn.

Superhost

Home in Round Top

4.96 out of 5 average rating, 198 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Superhost

Home in Kingston

4.99 out of 5 average rating, 115 reviews

Uptown kid/pet friendly yard, zoo, park & tennis

* Sunny Colonial, completely refurbished * Bright & airy with hardwood throughout * Across from Forsyth Park - walking trails, playground, petting zoo & tennis courts * Bring Rover - We love dogs & have a fully fenced-in yard * Fully equipped kitchen for family dinners * Central location to all Kingston amenities & 12 minute walk to historical Stockade District * 5-minute drive to public golf course (Wiltwyck Golf Club) * Fireplace, fire pit and BBQ * Family room in attic with foosball & games

Superhost

Flat in Pine Plains

4.98 out of 5 average rating, 177 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Superhost

Cottage in Cornwallville

4.93 out of 5 average rating, 113 reviews

Cozy Catskills Reteat with Geothermal Heat

Enjoy a peaceful retreat at the cottage, or use as a home base for exploring the Catskills. Family-friendly, private 4 bed, on a secluded 6.4 acre property. Enjoy coffee on the deck. Grill dinner and gather at the picnic table. Read on a blanket or lounge chair on the spacious private lawn. Relax by an evening campfire at the fire pit. Enjoy the living room fireplace, play board games, stream a movie. Or choose a more active Catskills adventure! Explore area hiking and swimming holes.

Superhost

Cottage in Cornwall

4.93 out of 5 average rating, 150 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Superhost

Guest suite in Charlemont

4.91 out of 5 average rating, 208 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Superhost

Farm stay in Coeymans Hollow

4.85 out of 5 average rating, 124 reviews

Magic Forest Farm’s Purple Palace

Our slice of paradise consists of 225 acres of forested land nestled in the foothills of the Catskills near Albany. We are a homestead and small community devoted to the principles of organic farming and self reliance. We grow much of our own food and forage many types of wild mushrooms. You will be sure to enjoy the spectacular mountain views, friendly farm animals, and secluded trails. The house is spacious and decorated with landscape oil paintings.

Superhost

Home in Palenville

4.96 out of 5 average rating, 166 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Superhost

Home in Germantown

4.97 out of 5 average rating, 331 reviews

Fantastic Cottage/Insane Views/Trails/Fireplace!

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ A Charming Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

Superhost

Tiny home in Nassau

4.94 out of 5 average rating, 142 reviews

Tiny Home 2 hrs NYC and BOS Lakefront WIFI

Extended stays are welcome! *** IMPORTANT *** Our photos previously showed screens enclosing the porch, but we have removed them due to wear from pets. Maintaining a pet-friendly environment is important to us, so the screens are no longer part of the tiny house. Enjoy a stay in our clean, charming, unique tiny home. This waterfront property features a private peninsula with a sandy entrance to the water.