
Family-friendly holiday rentals in West Windsor
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in West Windsor

Total holiday rentals
Explore 50 holiday rentals in West Windsor

Nightly prices starting at
West Windsor holiday rentals start at $153 NZD per night before taxes and fees

Verified guest reviews
Over 1,760 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of West Windsor holiday 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 family-friendly rentals in West Windsor
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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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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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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!
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Midcentury Hillside Retreat - Summer Paradise
Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.
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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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Ogden's Mill Farm
Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.
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Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.
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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.
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The Berghüttli: Glowing Swiss Hut in the Forest
The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.
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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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Okemo A-Frame - Floor Hammock, Sauna & Hot Tub
Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.
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Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board
Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th
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Popular amenities for West Windsor family-friendly rentals
Family-friendly home rentals with a hot tub

Alpine Reflection + Hot Tub
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forest retreat; off-grid writers cabin
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The Quechee Haus: VT Retreat with Outdoor Hot Tub
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Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
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The Owl’s Nest in Landgrove
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Relaxing Countryside Oasis!
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~The ClubHaus~
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Kolelemook Cottage!
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Family- and pet-friendly home rentals

Yurt In The Woods - Come to the Yurt.
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Private, Large 4BR home | Pet friendly | 10 Acres
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Apple Blossom Cottage: A Tiny House
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Copper Hill House - VT getaway near Ludlow & Okemo
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Luxury “Tiny” House With Sauna (Timbery)
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Private Hilltop farm apartment
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Charming Chester Farmhouse Near VT Slopes
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Adorable one bedroom studio in 1844 farmhouse.
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Family-friendly home rentals with a pool

Dream Catcher Farm
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On Pico Hike out back door 1 Bedrm 1 night okay
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Winterplace - Steps away from Slopes
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Golf and Mountain Biking outside the door!
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Ski-In/Out, AC, Pools, Hot Tub, Pet-Friendly
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Cozy Quechee Cabin near Woodstock and Killington
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Ski Mountain View Estate
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Beautiful Spacious Condo at Killington Resort
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When is the best time to visit West Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $446 NZD | $504 NZD | $416 NZD | $382 NZD | $379 NZD | $363 NZD | $501 NZD | $441 NZD | $538 NZD | $424 NZD | $428 NZD | $477 NZD |
| 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
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Portland Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Bar Harbor Holiday rentals
- 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
- Montshire Museum of Science
- Mount Sunapee Resort
- Camp Plymouth State Park
- Warren Falls





