Pet-friendly vacation rentals in Pittsfield

Find and book unique pet-friendly homes on Airbnb

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

Cabin in Royalton

4.99 out of 5 average rating, 202 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Superhost

Chalet in Stockbridge

4.86 out of 5 average rating, 135 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Superhost

Home in Rochester

4.9 out of 5 average rating, 288 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with large deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town of Rochester. 35 min. to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. *Snow tires or chains needed from Dec-March. When you book, please tell us that you saw the recommendation.*

Guest favorite

Farm stay in Salisbury

4.96 out of 5 average rating, 319 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This adorable cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Guest favorite

Rental unit in Royalton

4.98 out of 5 average rating, 173 reviews

Quiet Vermont Get Away

This space is ideal for a family or friends. This is a dog-friendly apartment located above our garage with stairs. Just 5 min off Exit 3 on I89. Full kitchen to make family meals. Cozy living/dining space. Come and stay for skiing, snowmobiling, hiking, biking, golf, local breweries and so much more depending on the season. Close to Vt Law School. 35-40 minutes to Killington, Pico, Stowe, Bolton and Sugarbush. 20 minutes to Quechee and Woodstock. Sleeps 5/6 with using a bunk bed.

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 638 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Guest favorite

Earthen home in Granville

4.9 out of 5 average rating, 102 reviews

Cozy Earthen Yurt in Mountains - Close to Skiing!

Secluded mountain wonderland near Vermont's best skiing and snowboarding! Enjoy a 25-acre homestead all to yourself, w/two beautifully-appointed yurts & a cabin. One-of-a-kind sculpted earth design, persian rugs, organic linens, & full kitchen w/many artisan touches. Stargaze around the fire circle under a glittering dark sky. A paradise for outdoor adventurers & nature lovers; a haven for digital nomads, writers, & creatives; a refuge of lush natural beauty & deep quiet.

Guest favorite

Cabin in Hancock

4.95 out of 5 average rating, 237 reviews

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 196 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Guest favorite

Cabin in Hancock

4.97 out of 5 average rating, 358 reviews

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

Superhost

Home in Pittsfield

4.84 out of 5 average rating, 226 reviews

Killington area home - 4-seasons & hot tub

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Guest favorite

Home in Rochester

4.95 out of 5 average rating, 186 reviews

The McKinley House

In the village of Rochester. Walk to bakery, cafe, tavern, grocery, and town green. Hiking, biking and Nordic ski trails! Thirty minutes to SugarBush, Pico, Middlebury, and Killington. Located in the heart of the Green Mountain National Forest. We are dog friendly but we require a conversation about it before you can show up with your dog. We charge $100 pet fee for your stay.