
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 $166 CAD 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 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!
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

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.

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

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!

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!

Private, Large 4BR home | Pet friendly | 10 Acres
Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.

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.

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.

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!

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.

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

Beautiful Historic 1909 Library with a Fireplace

SugarBear- Pool, AC, Sauna, Gym, Tennis!

Modern 3-bedroom A-frame in Londonderry w/ Pond

Cozy private cabin near Okemo! Large Hot tub!

Private & Cozy Farmhouse in New Hampshire

Convenient Home in Sunapee

Vermont private retreat with gorgeous views.

Heated Pool, EV Charging, Hot Tub & Barrel Sauna
Pet-friendly home rentals with a pool

Ski-In/Out, AC, Pools, Hot Tub, Pet-Friendly

Ranch at Mendon Mt Orchards

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Ski In/Out Spruce Glen C, AC, Sauna, Fireplace

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Vermont Horse Farm

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

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Private, pet-friendly home rentals

~The ClubHaus~

Cabin on the Hill

Modern Okemo Smart Cabin - As Seen On DIY Channel

The Owl’s Nest in Landgrove

Scandinavian design Cabin hiking trail + hot tub

Private Hilltop farm apartment

Private Cabin/PetsOK/AC/Minutes to Okemo/Fast Wifi

1958 Classic "Hunting Cabin" w/ Breathtaking Views
When is the best time to visit West Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $295 CAD | $326 CAD | $305 CAD | $309 CAD | $291 CAD | $291 CAD | $409 CAD | $298 CAD | $387 CAD | $327 CAD | $297 CAD | $329 CAD |
| 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 |
Destinations to explore
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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
- Middlebury College
- Hildene, The Lincoln Family Home
- Killington Resort
- Fox Run Golf Club
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- Squam Lakes Natural Science Center
- Stinson Lake
- Mount Sunapee Resort
- Montshire Museum of Science
- Camp Plymouth State Park
- Warren Falls





