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

Cabin in Royalton

4.99 out of 5 average rating, 174 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.

Dec 4 – 11

G$32,340 GYD per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 114 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.

Aug 24 – 31

G$32,438 GYD per night

Guest favorite

Farm stay in Salisbury

4.95 out of 5 average rating, 271 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.

Aug 10 – 17

G$26,680 GYD per night

Guest favorite

Guest suite in Castleton

4.98 out of 5 average rating, 122 reviews

Mi Casa es su Casa!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K TV, surround sound system. Wi-Fi access. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage. Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Dec 16 – 23

G$25,081 GYD per night

Guest favorite

Apartment in Royalton

4.98 out of 5 average rating, 149 reviews

Quiet Vermont Get Away

This space is ideal for a family or friends. Enjoy a relaxing and restful vacation at this dog-friendly 2nd story space with great views. 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, local breweries and so much more depending on the season.Close to Vt Law School. 35-40 minutes to Killington, Pico, Stowe, Bolton Valley and Sugarbush. 20 minutes to Quechee and Woodstock. Sleeps 5/6

Jan 12 – 19

G$28,240 GYD per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 592 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!

Nov 27 – Dec 4

G$29,919 GYD per night

Guest favorite

Cabin in Hancock

4.95 out of 5 average rating, 221 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.

May 9 – 16

G$30,543 GYD per night

Guest favorite

Home in Rochester

4.97 out of 5 average rating, 182 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!

Aug 22 – 29

G$33,721 GYD per night

Guest favorite

Cabin in Hancock

4.97 out of 5 average rating, 343 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.

Apr 17 – 24

G$34,569 GYD per night

Guest favorite

Apartment in Bethel

4.96 out of 5 average rating, 171 reviews

Fred Eddy Farmhouse

You will be renting an apartment in a renovated 1800’s farmhouse. The apartment is newly renovated with all the modern amenities. The place has a lot of charm but that being said the “main house” still needs to be completed. It’s not a brand new house, the exterior of the house has the rustic charm, there are windows waiting to be replaced, in the old farmhouse side I just wanted to make it clear pre-booking!

Nov 21 – 28

G$33,509 GYD per night

Guest favorite

Townhouse in Killington

4.93 out of 5 average rating, 199 reviews

Spacious 2 Bed/2 Bath Dogs Allowed, Spa Onsite

A cozy 2 bed 2 bath home in Killington. Nestled in The Woods, a luxury condo complex built on 100 acres of Vermont mountainside, this freshly renovated home is perfect for a dog-friendly retreat. Enjoy a spacious open living room and kitchen with a fireplace and stunning views. Complex amenities include an indoor pool and spa. Miles of hiking trails nearby! Contact us to book your stay!

Jun 15 – 22

G$36,821 GYD per night

Guest favorite

Home in Rochester

4.98 out of 5 average rating, 124 reviews

Modern Farmhouse on 25 Acres - Superb Views

This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Embracing the dramatic beauty of Rochester's north hollow the house is a serene retreat where connection to your partner, family and the environment will thrive. Unplug, recharge, renew and enjoy all that mountain living has to offer.

Dec 2 – 9

G$134,527 GYD per night