Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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

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Top guest favourite

Home in Woodstock

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

LocationValueBack garden

4.99 out of 5 average rating, 170 reviews

Top guest favourite

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guest house in Hartland

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

ValueLocationAccuracy

4.97 out of 5 average rating, 214 reviews

Top guest favourite

A sweeping view showcases Mt Ascutney, framed by vibrant autumn foliage. Rolling fields and meadows are seen in the foreground, with varying shades of green and gold. The landscape captures the tranquil essence of nature, inviting outdoor exploration.

Home in West Windsor

Chuck's Place

Summer is in full gear! Chuck's is a neat and tidy stand alone home warmly dedicated to your vacation pleasure. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. It's great for folks coming in for hiking, biking-- or absolute relaxation. Brownsville Butcher and Pantry supports many endurance and music events in the village at the base of Mt Ascutney. It's a special gathering place to enjoy wine, beer, ice cream --and the best meat and fish anywhere. We promise.

FamilyLocationBack garden

4.96 out of 5 average rating, 97 reviews

Guest favourite

Home in Cornish

Cornish-Windsor Bridge Retreat with Amazing Views

Set on the edge of the Connecticut River, this 6-bedroom, 2.5-bath home boasts amazing river and mountain views from sprawling wrap-around porches. Built in 1849, it has been respectfully updated with modern luxuries including a walk-in shower room with a clawfoot bathtub overlooking views of the river and mountain scenery. This location is an excellent starting point for exploring the many fine regional destinations including Saint-Gaudens National Historic Park, just two miles North.

LocationValueCheck-in

4.88 out of 5 average rating, 43 reviews

Top guest favourite

A charming red exterior defines the recently built house, surrounded by lush greenery and a clear sky. The spacious porch features rustic columns, while comfortable seating invites relaxation. Large windows ensure natural light fills the interior, offering a connection to the serene outdoor environment.

Home in Windsor

Custom cabin on Mt Ascutney, with faraway views

Combining sweeping views of distant hills with privacy and wraparound porches, the Red House is a custom cabin built for couples and smaller families getting away from busy lives. 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. It awaits the discerning traveler who can do absolutely nothing, yet experience it all!

LocationFamilyAmenities

4.97 out of 5 average rating, 137 reviews

Top guest favourite

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

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.

ValueLocationSolo travel

4.97 out of 5 average rating, 464 reviews

Top guest favourite

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

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.

LocationFamilyHeating

4.98 out of 5 average rating, 186 reviews

Top guest favourite

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

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.

LocationValueGetting around

4.97 out of 5 average rating, 240 reviews

Top guest favourite

A rustic cabin is nestled among vibrant wildflowers and lush greenery. A variety of flowers, including purple and yellow blooms, frame the scene, leading the eye towards the charming structure with a classic metal roof and wooden accents.

Home in West Windsor

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)

FamilyValueQuiet

4.98 out of 5 average rating, 240 reviews

Guest favourite

Cabin in West Windsor

Peaceful Vermont Cottage w/ Outdoor Sauna!

Escape to this cozy chalet-style home in Vermont’s tranquil woods, just 15 mins from Woodstock - with wood powered sauna! Perfect for outdoor fun—hike or bike Mt. Ascutney or Mt. Peg - Skiing at Saskedena 6, Killington and Okemo. All within a 30 minute drive! Come home to a wood powered Sauna waiting for you! Tucked at the end of a private road, it offers peaceful seclusion with easy access to nearby Woodstock and Windsor. *note - non operational fire place*

FamilyValueAmenities

4.85 out of 5 average rating, 84 reviews

Top guest favourite

Guest house in Hartland

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. In October, I require a two night stay with the exception of October 4 & 11. There is a "one" night stay fee of $50 - charged as extra services 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

ValueFamilyRiver

4.95 out of 5 average rating, 1067 reviews

Top guest favourite

Flat in Windsor

Charming apartment on the Windsor Green

This apartment is freshly refurbished and fully appointed. It has an old world charm and tastefully furnished. There is a full kitchen, beautiful new bathroom with shower, a bedroom and living room. The mattress is a queen tempurapedic. Just a few minutes walk brings one to Paradise Park, a conservation area with lovely walking trails. Walk the other way to Windsor Station restaurant or Boston Dreams for coffee and lunch. All of the Upper Valley is nearby.

LocationDecorGetting around

5.0 out of 5 average rating, 28 reviews