Pet-friendly vacation rentals in Windsor County

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

Custom cabin on Mt Ascutney, with faraway views

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Adorable one bedroom studio in 1844 farmhouse.

Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

Breathtaking Riverfront Retreat w/Mountain Views

Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

Sculpted Earthen Yurt in Green Mtns

Get away from it all in a wild mountain wonderland! Beautifully appointed yurts & a cabin surrounded by 25 acres of private forest, all to yourself. Hand-sculpted earth design, persian rugs, organic linens, & full kitchen w/many artisan touches. Explore local waterfalls and MTB trails, hike from the doorstep, make a campfire under a glittering, light-pollution-free sky. A private paradise for couples & outdoorsy families; a haven for writers & creatives; a quiet refuge to find yourself again.

Cozy VT Log Cabin Minutes to Okemo & Killington

Get away to Pine Ridge Cabin! A secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your morning coffee on the large wrap around deck overlooking Elm Brook before your day hiking, brewery hopping, or hitting the slopes! The cabin provides open floor plans centered around the large stone face fireplace, the perfect space for gatherings of family, friends, or a couples retreat! Pine Ridge Cabin is only a few minutes to town, shopping, restaurants, bars, and spa!

~The ClubHaus~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

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.

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

Meadow View. 35 acres outside your door!

Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. In October, I require a two night stay with the exception of October 4, 11 & 15th. There is a "one" night stay fee of $50 - charged as extra services Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network AC, Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available June - October