Holiday rentals in West Windsor

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Top-rated holiday rentals in West Windsor

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Top guest favourite

Home in Cavendish

5 out of 5 average rating, 115 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.

Guest favourite

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.

Top guest favourite

Cabin in West Windsor

4.97 out of 5 average rating, 251 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!

Top guest favourite

Cottage in Windsor

4.97 out of 5 average rating, 394 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 favourite

Tiny home in Hartland

4.96 out of 5 average rating, 195 reviews

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.

Top guest favourite

Home in West Windsor

4.98 out of 5 average rating, 124 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.

Guest favourite

Flat 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.

Top guest favourite

Guest house in Hartland

4.95 out of 5 average rating, 992 reviews

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

Top guest favourite

Cottage in Reading

4.94 out of 5 average rating, 160 reviews

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.

Top guest favourite

Flat 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.

Guest favourite

Flat in Claremont

4.89 out of 5 average rating, 150 reviews

Beautiful 1 bedroom apartment with balcony

Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

Guest favourite

Cabin in West Windsor

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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Other great holiday rentals in West Windsor

Guest favourite

Townhouse in Brownsville

5 out of 5 average rating, 54 reviews

Lovely Trailside 2 Bedroom Townhouse

GabrielaRating, 5 stars3 months ago

We had an amazing stay at Natalie’s place. The best Airbnb I have stayed at. Exceptionally clean, easy to get to, we felt right at home! Would highly recommend to anyone and hope to stay there again n my next ski trip.

Guest favourite

Cottage in Reading

4.9 out of 5 average rating, 77 reviews

Stone Wall Cottage, Stonewall : GMHA, Okemo

DavidRating, 5 stars1 month ago

Place was quite cute. Worth the $ for sure. It is fully detached from the owners home, and faces a gorgeous field and mountain. Hot water is a little on the limited side. Which isn’t really a complaint it’s just an observation and in no way impacted my stay there. But I am a guy and I can tell you that if my wife had come it may have been an issue for her. The unit was super clean, and we loved the old reclaimed wood everywhere. You will too.

Superhost

Guest suite in Brownsville

4.63 out of 5 average rating, 90 reviews

Cute, clean and comfy 2 BR studio

HelenRating, 5 stars4 months ago

Joseph’s place is great if you’re looking for a low key place to stay while skiing Okemo and Killington. The apt was clean and has everything you could need for a stay. The kitchen is more of a mini fridge and sink so don’t expect to cook anything — but the location is close to a great cafe (4 min drive) so we didn’t even have a need to cook. The beds were comfortable, the bathroom was clean and it felt very cozy. We would definitely stay there again.

Guest favourite

Cottage in Hartland

4.93 out of 5 average rating, 119 reviews

Adorable Dog Friendly Cottage w/FIOS

DylanRating, 5 stars1 week ago

Very cute cottage with lots of privacy and beautiful surroundings. Lulu was friendly and very accommodating with everything.

Guest favourite

Tiny home in Woodstock

4.99 out of 5 average rating, 136 reviews

The Cluck House

JohnRating, 5 stars2 weeks ago

I really loved staying at the Cluckhouse. It was truly so beautiful and peaceful, a tranquil space that honestly was almost fairytale beautiful (even in the quiet rain of one of the days), while also being only 10 mins from the town Woodstock. Tina was an amazing host; she reached out well before I arrived with directions and suggestions, she was extremely thoughtful once I arrived, and, most importantly, a wonderful person with a calm peaceful energy; I really enjoyed talking to Tina whenever I’d come thru the kitchen. I’d love to stay here again

Guest favourite

Guest house in Hartland

4.96 out of 5 average rating, 180 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

AmandaRating, 5 stars5 months ago

Beautiful place to stay at an affordable price! I recommend wholeheartedly. Host was friendly and helpful. The space was clean. I couldn’t have asked for a better place.

Superhost

Home in West Windsor

4.86 out of 5 average rating, 73 reviews

Cozy historic hilltop cottage

JamesRating, 5 stars8 months ago

The cottage is quaint and charming. The exposed ceiling beams and peg-and-blank flooring shows the history of the old school house turned into a home. A record player is available with a stack of vinyl classics to play was a nice touch. I will recommend the host update the pictures in the listing to reflect the changes that have been made. The wood stove in the living room has been removed and replaced with an oddly arranged cabinet and television. The bath has some upgrades. The kitchen is functional and handled the simple meals we prepared. The best part was the back deck facing the valley. We sat and watched the fog roll in, and enjoyed the sunshine. I would recommend this place to get away from things.

Guest favourite