
Vacation rentals in West Windsor
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Top-rated vacation rentals in West Windsor
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Private Riverside Studio* Upper Valley*Vermont
This unique place has a style all its own. Perfect for a traveling nurse or anyone who needs a relaxing getaway or a remote place to work. This studio apartment has river and garden views and is conveniently located in the New England Village of North Hartland. A 15-20 minute drive to Dartmouth College or DHMC. Take country walks across the twin covered bridges right from your doorstep. Relax on the front porch and watch the bald eagles and peregrine falcons search for prey along the river.

The Old Farmhouse
This is a farm house style lodging with the apartment as seen,on the second floor accessible with stairs. Bathroom with stand up shower. A furnished Kitchen. 2 Bedrooms with queen beds. There is Wifi ,TV, and a work table. Located in the heart of the Upper Valley. In town on the Main Street. We are 5 miles to Dartmouth College and Hospital. Close to retail,restaurants. We have been vaccinated , boosted, would like to remain contact-free when possible. We are available if you have questions.

Newly renovated private space on Ascutney Trails
Newly renovated private space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, Maple Kitchen Restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Air conditioned during the summer. Television and fast wifi.

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.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

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.

Private guesthouse in Lebanon
This cozy one-room guesthouse is located on a quiet street off the green in downtown Lebanon, NH. It offers a private entrance with access to a lovely outdoor patio and gas grill. The room has high ceilings, a full-sized bed, a bathroom/shower, and a kitchenette with coffee maker, electric kettle, microwave, toaster, and compact fridge. A short walk away from restaurants and cafes and a 12-minute drive to Dartmouth College. Please note that there is no kitchen sink or stove.

The Loft at Weathersfield
Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

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)

Cozy Little Spot (Self Check-in)
Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

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.

Cowshed Cabin Farm
Charming 12 year old cabin located in the heart of dirt roads, trails and close to skiing, hiking and horseback riding activities. Fully furnished, wifi, TV, washer and dryer, microwave, coffee maker, gas grill (summer). Property is adjacent to owners' cabin. Dogs allowed. Horses allowed May through Oct. Upgraded wifi capabilities to ensure strong wifi signal throughout the cabin.
Popular amenities for West Windsor vacation rentals
Other great vacation rentals in West Windsor

Lovely Trailside 2 Bedroom Townhouse

Country Home next to Covered Bridge

Secluded Getaway, VT - 15 min from Woodstock

Elm Gate Farm

Vermont Botanical Studio Apartment

Peaceful Vermont Cottage w/ Outdoor Sauna!

Red Barn Cabin Near Okemo

THE LOFT, stunning views from a timber framed barn
When is the best time to visit West Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $289 CAD | $289 CAD | $289 CAD | $280 CAD | $275 CAD | $282 CAD | $296 CAD | $287 CAD | $296 CAD | $315 CAD | $275 CAD | $355 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 |
Frequently Asked Questions
Do house rentals in West Windsor have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in West Windsor?
West Windsor has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in West Windsor?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in West Windsor?
Four-legged friends are welcome in West Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there West Windsor vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in West Windsor, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in West Windsor?
Yes! Work meets play with ease at over 20 vacation rentals in West Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in West Windsor?
Experience the best of West Windsor with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in West Windsor have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in West Windsor have wifi?
Absolutely! We offer over 20 house rentals with wifi in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in West Windsor have free parking?
Absolutely! We offer over 20 house rentals with free parking in West Windsor. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in West Windsor

Total vacation rentals
Explore 60 vacation rentals in West Windsor

Nightly prices starting at
West Windsor vacation rentals start at $124 CAD per night before taxes and fees

Verified guest reviews
Over 2,560 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
60 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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- Apartment rentals West Windsor
- Rentals with a washer and dryer West Windsor
- Rentals with a firepit West Windsor
- Rentals with outdoor seating West Windsor
- Rentals with a fireplace West Windsor
- Pet-friendly rentals West Windsor
- House rentals West Windsor
- Rentals with a patio West Windsor
- Rentals with pools West Windsor
- Family-friendly rentals West Windsor
- Fitness-friendly rentals West Windsor
- 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
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Dorset Field Club
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- The Shattuck Golf Club
- Brattleboro Ski Hill
- Autumn Mountain Winery
- Northeast Slopes Ski Tow




