
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.

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

Fat Cat Barn - Close Okemo & Magic, Vermont
Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Adorable Dog Friendly Cottage w/FIOS
Bright and clean 2-story cottage on a 20-acre oasis. 10% off for guests using only one bedroom (cannot be combined with other discounts). Details in property description. 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. For groups or more space, view my other listing located on the same acreage: airbnb.com/h/hartlandvacationhome

Contemporary Ascutney Cabin near Ski Areas
On a cold winter morning Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views. Grab a hot coffee with a book from our library. Hot mug in hand, step out to the porch, look at faraway hills. Make breakfast in the Chefs kitchen. Snowshoe/slide/talk/play with your favorite people/animals in the world. Take a scenic drive to Woodstock, Simon Pearce, Okemo, or the Harpooon Brewery. Kick back with a night around the firepit stargazing Sharing our Red House with you.

Historic Home on 17 acres of land. Go escape!
This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool will be reopened around May 2025 (weather dependent. It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything ask!

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.

Sunny Side Airbnb (dog friendly)
Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

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.

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.

River House Apartment - Dog friendly
Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

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)

Vermont Retreat Near Okemo | 3BR w/ Fireplace
Peaceful 3BR Vermont Estate Near Woodstock & Mt. Ascutney Escape to our serene Vermont retreat on 7 private acres. Just 5 minutes from Mt. Ascutney trails and 15 minutes from Green Mountain Horse Association. Perfect for families, riders, and nature lovers, our modern country home blends comfort with classic Vermont charm. Whether you’re planning a quiet couples’ retreat or a family getaway full of Vermont adventure, you’ll find space, serenity, and style here.
Popular amenities for West Windsor pet-friendly home rentals
Pet-friendly house rentals

Beautiful Historic 1909 Library with a Fireplace

Top of the World! Jacuzzi! Private Hiking Trails!

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

Beautiful Woodstock Home-Perfect for entertaining

The Grafton Chateau

Blueberry Hill Escape | Pet Friendly | HotTub | Fi

Charming, Cozy Cape

Private & Cozy Farmhouse in New Hampshire
Pet-friendly home rentals with a pool

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Ranch at Mendon Mt Orchards

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

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

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

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

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

Convenient and chic private suite with 2 bedrooms!

Cabin on the Hill

The Owl’s Nest in Landgrove

Newport Jail “Break”

Private Cabin/PetsOK/Minutes to Okemo/Fast Wifi

Red Barn Cabin Near Okemo

Cozy Mountain Cabin w/ Hot Tub & Incredible View

Charming Cavendish Guesthouse
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.ﺇ441 per night before taxes and fees

Verified guest reviews
Over 1,320 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!
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- Rentals with a fireplace West Windsor
- Family-friendly rentals West Windsor
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- Pet-friendly rentals Windsor County
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- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Dartmouth Skiway
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- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Dorset Field Club
- Hooper Golf Course
- Whaleback Mountain
- Lucky Bugger Vineyard & Winery
- The Shattuck Golf Club
- Fox Run Golf Club
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
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