
Pet-friendly vacation rentals in West Windsor
Find and book unique pet-friendly homes on Airbnb
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 ﺩ.ﺇ 441 per night before taxes and fees

Verified guest reviews
Over 1,560 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of West Windsor vacation rentals include wi-fi 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!
Top-rated pet-friendly home rentals in West Windsor
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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
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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.
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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
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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!
PetsOutdoor spacesBackyard

~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
Outdoor spacesPetsTV

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.
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Luxury “Tiny” House With Sauna (Timbery)
The Timbery: This is a new, fully handmade, timber frame "tiny" house featuring a custom Norwegian Sauna. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down in a tent on the forest floor, except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen, sauna and 71in soaking tub.
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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.
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Charming Chester Farmhouse Near VT Slopes
Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!
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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.
WalkabilityOutdoor spacesFamily

Greystone 1830
"Greystone" is a charming stacked granite home built in the 1830's as a tavern and one of 4 original structures that made up Hammondsville VT. Greystone is just miles from Woodstock, and down the road from the Green Mountain Horse Association (GMHA). It's a short drive to Killington or Okemo and many other Vermont destinations. Greystone is just off VT Rt 106 on a large lot with a circular driveway and plenty of room for parking. The home is fully renovated and modernized.
WalkabilityOutdoor spacesNearby

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)
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Popular amenities for West Windsor pet-friendly home rentals
Pet-friendly house rentals

Beautiful Historic 1909 Library with a Fireplace
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Mountain Getaway Pet friendly
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The Post Haus - One-of-A-Kind Modern VT Experience
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Modern 3-bedroom A-frame in Londonderry w/ Pond
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Comfortable farmhouse with stunning views
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Charming, Cozy Cape
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Private, Large 4BR home | Pet friendly | 10 Acres
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Vermont private retreat with gorgeous views.
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Pet-friendly home rentals with a pool

AC | Dog-Friendly | Bike, Hike & Relax
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Ranch at Mendon Mt Orchards
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Ski In/Out Spruce Glen C, AC, Sauna, Fireplace
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2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
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Vermont Horse Farm
Outdoor spacesPetsBackyard

Chalet | Heated Pool + Hot Tub | near Stratton, VT
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Topridge 3BR w Incredible View & Private Hot Tub!
Outdoor spacesAmenitiesCleanliness

Beautiful Bromley/Manchester VT Retreat w/hot tub
Outdoor spacesWalkabilityLocation
Private, pet-friendly home rentals

Scandinavian design Cabin hiking trail + hot tub
WalkabilityOutdoor spacesKitchen

Private Hilltop farm apartment
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Adorable one bedroom studio in 1844 farmhouse.
WalkabilityOutdoor spacesCleanliness

Private Cabin/PetsOK/AC/Minutes to Okemo/Fast Wifi
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Peaceful Vermont Cottage w/ Outdoor Sauna!
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Stunning Rustic Apple Barn - hot tub & sauna
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Charming Cavendish Guesthouse w/ Sauna!
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Spacious Renovated Barn Apt on 100 acres!
WalkabilityOutdoor spacesSkiing
When is the best time to visit West Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 782 | ﺩ.ﺇ 863 | ﺩ.ﺇ 808 | ﺩ.ﺇ 819 | ﺩ.ﺇ 771 | ﺩ.ﺇ 771 | ﺩ.ﺇ 1,083 | ﺩ.ﺇ 790 | ﺩ.ﺇ 1,025 | ﺩ.ﺇ 867 | ﺩ.ﺇ 786 | ﺩ.ﺇ 870 |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
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- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Dartmouth College
- Tenney Mountain Resort
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Middlebury College
- Killington Resort
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Squam Lakes Natural Science Center
- Stinson Lake
- Montshire Museum of Science
- Mount Sunapee Resort
- Camp Plymouth State Park
- Warren Falls
- Plymouth State University





