Pet-friendly holiday rentals in Windsor County

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.

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.

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.

Ski On/Ski Off - Dog-Friendly Mountainside Retreat

Experience year-round adventure at Sunrise Village at Killington, offering a true ski-in, ski-out location just steps from the Sun Dog Trail and Sunrise Village Triple Lift (488 ft away). After a day of skiing or exploring, unwind by the cozy electric fireplace. Outdoor enthusiasts will love the hiking, mountain biking, kayaking, and golfing nearby. The indoor sports complex, featuring a pool, hot tub, and gym, is just a short walk away. Come enjoy and make unforgettable memories!

Mimi's Place - pets welcome!

Escape to this charming 1BR/1BA apartment in central Rutland Town! Perfectly located for outdoor adventures - it's a stone’s throw from skiing, hiking, and the vibrant Rutland City's scene. Enjoy a full kitchen, cozy living area, and the convenience of an in-unit washer/dryer. Bring your furry friends along! Whether you’re hitting the slopes or exploring local shops and dining, this is your ideal retreat for relaxation and adventure. Book now and experience the best of Vermont!

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.

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.

Adorable Dog Friendly Cottage w/FIOS

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 (cannot be combined with other discounts). See details in property description. Pet sitting available - please inquire for rates & info.

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.