Vacation rentals in West Windsor

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Top-rated vacation rentals in West Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A rustic cabin surrounded by tall trees is showcased. A light-colored entrance door and two windows are displayed at the front. Adjoining the cabin, a grassy area features a stone pathway leading to a pair of white adirondack chairs, inviting relaxation.
Guest suite in Hartford
4.88 out of 5 average rating, 158 reviews

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.

Top guest favorite
Tiny home in Chester
4.99 out of 5 average rating, 110 reviews

Tiny A-Frame Rest House in Woods near Mountains

Newly built A-Frame getaway cabin built in the middle of the woods of Vermont. Unplug from it all at this special space surrounded by nature. Enjoy doing yoga and relaxing on the deck, remote working with fiber optic wifi, utilizing the fire pit to roast smores, or taking a walk around the walking paths on the property! There are also nearby hikes, swimming spots, skiing destinations, and drinking/eating spots! We are 35-40 minutes from Stratton, Mount Snow, Bromley, Okemo, and Magic Mountain!

Top guest favorite
A serene outdoor area is visible, featuring a gravel patio with a dining table surrounded by chairs. Vibrant purple flowers frame the scene, while a tranquil pond and greenery provide a backdrop. The space is illuminated by bright sunlight, creating a relaxed atmosphere.
Home in Sharon
4.99 out of 5 average rating, 122 reviews

The Willow House: a Modern Vermont Retreat

Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

Top guest favorite
Home in Cavendish
5 out of 5 average rating, 128 reviews

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.

Top guest favorite
The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.
Barn in Woodstock
4.99 out of 5 average rating, 306 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Top guest favorite
Cottage in Windsor
4.97 out of 5 average rating, 447 reviews

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.

Top guest favorite
A wooden deck leads to a well-lit entrance, featuring a glass door flanked by two large windows. A cozy couch is arranged on the deck, complemented by potted plants and a railing that enhances the view of the surroundings.
Home in West Windsor
4.98 out of 5 average rating, 180 reviews

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.

Top guest favorite
The exterior of a modern blue house is depicted, featuring a combination of angular roofs and large windows allowing for ample natural light. A stone wall borders the property, which is surrounded by lush greenery and trees in the background.
Apartment in Weathersfield
4.99 out of 5 average rating, 191 reviews

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.

Top guest favorite
Home in West Windsor
4.98 out of 5 average rating, 229 reviews

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)

Top guest favorite
Guesthouse in Woodstock
4.98 out of 5 average rating, 295 reviews

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.

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny home in Athens
4.86 out of 5 average rating, 179 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Top guest favorite
A wooden deck with three textured planters greets guests upon entry. A vibrant flower pot adds color beside a gas grill, situated among lush greenery. A hula hoop hangs nearby, enhancing the outdoor space's playful atmosphere.
Guesthouse in Hartland
4.95 out of 5 average rating, 1,050 reviews

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. The month of October I require a two night stay. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network AC, Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available June - October

Popular amenities for West Windsor vacation rentals

When is the best time to visit West Windsor?

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Avg. price€185€205€191€177€173€178€186€181€186€190€185€205
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in West Windsor?

    West Windsor has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 vacation rentals with a dedicated workspace in West Windsor?

    Yes! Work meets play with ease at over 30 vacation rentals in West Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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!

  • Do house rentals in West Windsor have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in West Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in West Windsor have a kitchen?

    Absolutely! We offer over 10 cabin rentals with a kitchen in West Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in West Windsor have wifi?

    Absolutely! We offer over 10 cabin 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 10 house rentals with free parking in West Windsor. Enjoy a tailored experience with all the comforts you desire.

  • 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 wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in West Windsor

  • Total vacation rentals

    Explore 70 vacation rentals in West Windsor

  • Nightly prices starting at

    West Windsor vacation rentals start at €78 per night before taxes and fees

  • Verified guest reviews

    Over 2,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & 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

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 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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