
Pet-friendly vacation rentals in West Windsor
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Top-rated pet-friendly home rentals in West Windsor
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Stylish Vermont Cabin | Views · Trails · Luxe
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.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

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.

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Sugar River Treehouse
Welcome to Sugar River Treehouse! If you’re looking for serenity, peace and quiet, in the most unique, breathtaking, beautiful setting, you have found it. On top of the trees, overlooking the Sugar River in the quaint town of Newport, NH you will find plenty of year round activities including swimming, floating, fishing on the beautiful, clear Sugar River, right outside the back door. You will find the treehouse sits up in between 2 beautiful northern hemlocks and is fully equipped inside.

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.

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.

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.

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)

7-Acre VT Estate | Barn, Trails & Mountain Views
Peaceful 3BR home Near Woodstock & Mt. Ascutney Step onto seven private acres where mountain views stretch to the horizon and the only sounds are birdsong and the rustle of leaves. This modern country home is the rare Vermont retreat that has it all - room to roam, horses welcome, and enough comfort inside to make you forget about unplugging was ever hard. Whether you're here to ride, hike, explore Woodstock's villages, or simply do nothing, this is your base.

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. 2 night stays required for Weekends. The month of October I require a two night stay. There is a "one" night stay fee of $50 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
Popular amenities for West Windsor pet-friendly home rentals
Pet-friendly house rentals

The Post Haus: one-of-a-kind modern VT experience

Comfortable farmhouse with stunning views

Private & Cozy Farmhouse in New Hampshire

Charming, Cozy Cape

Convenient Home in Sunapee

Convenient Vermont Getaway

Vermont private retreat with gorgeous views.

Renovated Vermont Schoolhouse – Close to Okemo
Pet-friendly home rentals with a pool

AC | Dog-Friendly | Bike, Hike & Relax

Ranch at Mendon Mt Orchards

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

SKI ON/OFF Spruce Glen C | AC | Fireplace | Sauna

Chalet | Heated Pool + Hot Tub | near Stratton, VT

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Private, pet-friendly home rentals

Scandinavian design Cabin hiking trail + hot tub

Hideaway Cabin by the Stream on 27 Acres

Classic Vermont A-Frame | Fire Pit | Near Stratton

100 Acres Views & Creek near Woodstock/Killington

Cozy 4-season Cabin on Pond - "East Cabin"

Red Barn Cabin Near Biking Trails, Woodstock, GMHA

Peaceful Vermont Cottage w/ Outdoor Sauna!

Mountain side acres
Quick stats about vacation rentals that are pet-friendly in West Windsor

Total vacation rentals
Explore 20 vacation rentals in West Windsor

Nightly prices starting at
West Windsor vacation rentals start at $168 CAD per night before taxes and fees

Verified guest reviews
Over 1,510 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of West Windsor vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across West Windsor rentals

4.9 Average rating
West Windsor stays are highly rated by guests—averaging 4.9 out of 5!
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- Pet-friendly rentals Windsor County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Killington Resort
- Dartmouth College
- Bromley Mountain Ski Resort
- Middlebury College
- Montshire Museum of Science
- Mount Sunapee Resort
- Squam Lakes Natural Science Center
- Emerald Lake State Park
- Stinson Lake
- Mount Monadnock
- Camp Plymouth State Park





