Vacation rentals in West Windsor

Guest suite in Brownsville

4.89 out of 5 average rating, 130 reviews

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.

4.94 out of 5 average rating, 1,269 reviews

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

4.97 out of 5 average rating, 249 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

4.97 out of 5 average rating, 393 reviews

Cottage in Windsor

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.

4.96 out of 5 average rating, 193 reviews

Tiny home in Hartland

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.

4.98 out of 5 average rating, 124 reviews

Home in West Windsor

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.

Apartment in Weathersfield

4.99 out of 5 average rating, 175 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.

4.95 out of 5 average rating, 992 reviews

Guesthouse in Hartland

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require at least a two night stay for the whole month of October. There is a "one" night stay fee of $40 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

4.94 out of 5 average rating, 160 reviews

Cottage in Reading

Shattuck Hill Cottage

Cozy two bedroon one bath cottage on 12 acres perfect for a visit to the Woodstock area. The cottage is 6 miles from the Green Mountain Horse Association. Our property connects to miles of riding and hiking trails. We have fenced pasture for your horse, a run in shed and are directly on the dirt roads and trails. You can ride, ski, snowshow, bike, hike or antique from our cottage. Come enjoy all Vermont has to offer. This is a non smoking property.

4.99 out of 5 average rating, 136 reviews

Tiny home in Woodstock

The Cluck House

The Cluck House (360sq. ft) was converted from a chicken coop into a 1 bedroom guest space in the 1950’s. Today it is still used for extra sleeping quarters during the warmer months (May 15-Oct 15). Please Note: The Private Full Bathroom Is Located In The Main Farmhouse, just a short walk across the lawn. We are pet friendly and welcome guests who wish to travel with them. We charge a $35 Cleaning Fee per trip.

Apartment in Weathersfield

4.97 out of 5 average rating, 133 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

4.96 out of 5 average rating, 143 reviews

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.

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Popular amenities for West Windsor vacation rentals

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Air conditioning

Other great vacation rentals in West Windsor

5 out of 5 average rating, 3 reviews

Cabin on the Hill, Vermont

JackRating, 5 stars3 months ago

Patrick’s cabin was a fantastic experience, great value and just a short drive to Killington Mountain Resort. The cabin itself was cozy and well-equipped, featuring a beautiful kitchen, comfortable La-Z-Boy couches, and a PlayStation 5 for gaming or watching movies. One of the highlights was the nearby Brownsville Butcher & Pantry, which has an incredible menu, easily one of the best I’ve had. There’s also a cool bar and brewery, Harpoon Brewery Taproom, not too far away in town. Overall, a great stay, and we’d definitely visit again!

4.97 out of 5 average rating, 58 reviews

Cabin in Cavendish

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

AnnaRating, 5 stars3 weeks ago

What a great getaway! My husband and I had a great weekend! We would’ve done more outside the cabin like using the hot tub, kayaks and fire pit, but unfortunately it rained most of the weekend. We were able to easily explore local sights like driving up Okemo mountain, walking around Ludlow and Killington and went to the farmers market in Rutland. I would definitely recommend this stay!

Superhost

Tiny home in Hartland

4.97 out of 5 average rating, 38 reviews

Cozy tiny house w/private hot tub

LaurenRating, 5 stars3 weeks ago

Our stay was great and the tiny house was perfect for a quick weekend away. The hot tub was awesome and the house had everything we needed. The highway is very close and loud but if that doesn’t bother you then you’ll be fine! We would definitely book here again.

5 out of 5 average rating, 13 reviews

Home in West Windsor

Elm Gate Farm

AlexRating, 5 stars3 months ago

We had the best weekend away at Anne's farmhouse! The space is generous, and despite being attached to the main house, felt very private. Anne was so warm and accommodating, even including several age appropriate toys for my two kids, a bowl full of fresh eggs for her chicken flock, and coffee supplies. The highlights of the weekend included a chance for the kids to see and feed some of the animals. The space was well equipped, clean and comfortable.

Home in Brownsville

5 out of 5 average rating, 4 reviews

Skyhawk Cabin: refined modern getaway with hot tub

AlexRating, 5 stars3 months ago

Great place for a big group of people. Host was responsive and helpful when we typed in the wrong code (100% our fault) and needed help. Among other places in a neighborhood just past the little ski/tubing mountain. Recommend Butcher and Pantry just down the street for groceries! Our stay was in the winter, driveway was icy (definitely need AWD!! And some good snow boots!). We only had 2 couples, but would have felt like a good bang for the buck if there were more people. Overall, clean, basic, good for a group!

5 out of 5 average rating, 48 reviews

Tiny home in Brownsville

Red Barn Cabin Near Okemo

RachelRating, 5 stars2 weeks ago

What a wonderful home! My husband and I and our dog had a great time staying at this tiny house. Such thoughtful touches, peaceful (especially with the bubbling brook in the back), and so cozy. Lots to do in the area, and only a 5 minute drive to Mt. Ascutney for hiking. Mark was super responsive and provided helpful recommendations. We loved staying here and would 100% recommend to anyone!!