Pet-friendly holiday rentals in Windsor County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Windsor County

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

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Guest favourite

Home

4.89 out of 5 average rating, 134 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Guest favourite

Tiny home

4.89 out of 5 average rating, 209 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Guest favourite

Home

4.93 out of 5 average rating, 108 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Superhost

Home

4.9 out of 5 average rating, 289 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with 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. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

Guest favourite

Guest suite

4.91 out of 5 average rating, 366 reviews

Sunny Side Airbnb (dog friendly)

Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

Guest favourite

Flat

4.98 out of 5 average rating, 175 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 favourite

Home

4.93 out of 5 average rating, 203 reviews

Porch House

Cozy house in the heart of Rochester village. Antiques and books abound, all modern amenities. Wrap around porch delightful in the summer. Walk to grocer, restaurants, pub, bakery, bookstore, art gallery, bike shop, yoga studio, farmer's market, river. Nice trails right behind house. Hiking, swimming holes, tubing, downhill/backcountry/x-country skiing, mountain/road biking, golf courses, craft breweries, distilleries, all nearby. 30 min drive to Killington/Sugarbush/Middlebury.

Superhost

Townhouse

4.87 out of 5 average rating, 242 reviews

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

Guest favourite

Home

4.95 out of 5 average rating, 238 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favourite

Apartment

4.96 out of 5 average rating, 102 reviews

Mountainside Retreat - Dog-Friendly!

Enjoy year-round activities at Sunrise Village at Killington. Our location offers a true ski-in ski-out experience near the Sun Dog trail and the Sunrise Village Triple lift(488 ft away). Relax in front of the cozy electric fireplace. Outdoor enthusiasts can enjoy hiking, mountain biking, kayaking, and golf. Come and experience the fun at Sunrise Village. The outdoor amenities (short walk away) are open from dawn to dusk - pool, hot tub, grills

Superhost

Home

4.91 out of 5 average rating, 11 reviews

Cute & cozy 2 bedroom home.

Updated 2 bedroom home in Mendon, VT. Convenient location; 6 minutes from Pico, 10 minutes from Rutland, and 13 minutes to Killington. I’m sharing my place with others so they can vacation with their dogs and children. (While I like cats, we're allergic). We recommend snow tires, or 4-wheel drive to get up the small hill to the house. Finally, be careful as it is on the main highway. If you're looking for comfort & convenience, this is it.

Guest favourite

Cottage

4.92 out of 5 average rating, 106 reviews

Hartland - Adorable Cottage w/FIOS - Dog Friendly

Bright and clean 2-story cottage on a shared 20-acre sanctuary. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bathroom (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. 10% discount for guests using only one bedroom, reimbursed at the end of your trip via AirB. See details in property description.