Pet-friendly vacation rentals in West Windsor

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in West Windsor

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, 146 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

Guest favorite

The living area features a cozy sofa adorned with decorative pillows, positioned around a central coffee table. Natural light enters through a large window beside the door, illuminating the wood-paneled walls and rustic floor. A simple area rug adds texture to the space.

Cottage in Hartland

4.93 out of 5 average rating, 119 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a 20-acre oasis. 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 bath (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. 10% off for guests using only one bedroom (cannot be combined with other discounts). Details in property description. For groups or more space, view my other listing located on the same acreage: airbnb.com/h/hartlandvacationhome

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, 373 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

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

4.94 out of 5 average rating, 1,269 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

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, 249 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 guesthouse with a red exterior is set against a backdrop of vibrant greenery and colorful flower beds. Various flowers in shades of orange, pink, and purple border the property, while tall trees provide natural shade. The tranquil setting invites relaxation in nature.

Guesthouse in Wallingford

4.98 out of 5 average rating, 697 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!

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, 193 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, 992 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 , Outdoor Fire Circle, and Outdoor Shower 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, 160 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

A spacious living area features a large, yellow sofa paired with a circular coffee table. Two comfortable chairs in rust color are positioned nearby. A vintage-style stove is present against the wall, with soft lighting provided by wall sconces. A door leads to another room.

Guesthouse in Cavendish

4.95 out of 5 average rating, 151 reviews

Cozy Cavendish Bunkhouse

Enjoy a stylish & relaxing experience at this centrally-located guest home. Newly renovated with local interior designer! The bunkhouse is behind our main house. We're a quick 10 minute drive to Okemo Ski Resort! You can enjoy plenty of nature, hiking, snowmobiling, mountain biking, skiing/snowboarding and much more in the area! Follow the Bunk House on IG where we’ll share all the local happenings!! ‘at’cozycavendishbunk We look forward to hosting you!

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, 136 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, 143 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.