Pet-friendly vacation 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 favorite

An exterior view of the modern house is highlighted, featuring large, south-facing windows that reflect daylight. Surrounded by snow, a wooden deck is set with a dining table and chairs, along with a fire pit area, creating an inviting outdoor space.

Home in Barnard

4.99 out of 5 average rating, 144 reviews

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Top guest favorite

A cozy cabin interior features a wooden ceiling with exposed beams. A spacious bed is adorned with a colorful quilt of leaves. A kitchenette with appliances and a dining area can be seen along one wall, while light pours through the window adorned with a patterned curtain.

Cabin in Royalton

4.99 out of 5 average rating, 214 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.

Guest favorite

An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.

Guesthouse in Springfield

4.85 out of 5 average rating, 372 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Guest favorite

An outdoor area is presented, featuring a green lawn bordered by trees. A wooden deck with a red umbrella is visible, accompanied by a seating arrangement with striped chairs. A walking path leads into a natural landscape, enhancing the setting's tranquility.

Guest suite in Hartford

4.91 out of 5 average rating, 382 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.

Top guest favorite

A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.

Cabin in Stockbridge

4.95 out of 5 average rating, 108 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Top guest favorite

The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.

Cabin in West Windsor

4.97 out of 5 average rating, 247 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

Top guest favorite

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

4.96 out of 5 average rating, 192 reviews

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Top guest favorite

The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.

Guesthouse in Hartland

4.95 out of 5 average rating, 990 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require at least a two night stay for the whole month of October. There is a "one" night stay fee of $40 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas grill available May - October Outdoor Fire Circle available May - October

Top guest favorite

The exterior of the cottage features dark blue siding with white window frames. Two windows are adorned with flower boxes, while two green chairs are positioned on the patio. A small deck is visible to the left, surrounded by lush greenery.

Cottage in Reading

4.94 out of 5 average rating, 159 reviews

Shattuck Hill Cottage

Cozy two bedroon one bath cottage on 12 acres perfect for a visit to the Woodstock area. The cottage is 6 miles from the Green Mountain Horse Association. Our property connects to miles of riding and hiking trails. We have fenced pasture for your horse, a run in shed and are directly on the dirt roads and trails. You can ride, ski, snowshow, bike, hike or antique from our cottage. Come enjoy all Vermont has to offer. This is a non smoking property.

Guest favorite

The inviting bedroom features a queen-sized bed adorned with a colorful floral-patterned blanket. A gray sofa adds comfort alongside a small lamp and nightstand. Soft light fills the room, highlighting the vibrant green walls and decorative wall accents.

Guesthouse in Hartford

4.87 out of 5 average rating, 111 reviews

Addie's Place

A cozy and quiet space close to Dartmouth College (8 mins), Dartmouth Hitchcock Hospital (12 mins), and White River Junction Center (5 mins). You will have a private entrance to the space and access to a yard, a 3 season patio room, bedroom with a queen sized bed and queen pullout couch, a separate dining area, grill, and a private bathroom. There is no kitchen but there is a mini fridge, table, coffee/tea bar, plates, utensils, mugs, and a microwave.

Guest favorite

The Cluck House is depicted in a serene setting, nestled among lush green grass and colorful flowerbeds. A flowering tree stands nearby, while the main farmhouse is visible in a blue hue, providing a picturesque backdrop to this charming guest space.

Tiny home in Woodstock

4.99 out of 5 average rating, 134 reviews

The Cluck House

The Cluck House (360sq. ft) was converted from a chicken coop into a 1 bedroom guest space in the 1950’s. Today it is still used for extra sleeping quarters during the warmer months (May 15-Oct 15). Please Note: The Private Full Bathroom Is Located In The Main Farmhouse, just a short walk across the lawn. We are pet friendly and welcome guests who wish to travel with them. We charge a $35 Cleaning Fee per trip.

Guest favorite

The exterior of a rustic log cabin is displayed, featuring a metal roof and multiple windows with white trim. Snow covers the ground, enhancing the natural surroundings. A deck can be seen alongside the cabin, providing outdoor space for guests.

Cabin in West Windsor

4.96 out of 5 average rating, 141 reviews

Cowshed Cabin Farm

Charming 12 year old cabin located in the heart of dirt roads, trails and close to skiing, hiking and horseback riding activities. Fully furnished, wifi, TV, washer and dryer, microwave, coffee maker, gas grill (summer). Property is adjacent to owners' cabin. Dogs allowed. Horses allowed May through Oct. Upgraded wifi capabilities to ensure strong wifi signal throughout the cabin.