Vacation rentals with breakfast in Windsor County

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Top-rated breakfast rentals in Windsor County

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Guest favorite

A gravel patio features five yellow Adirondack chairs arranged around a central firepit, surrounded by freshly cut grass. A wooden fence borders a lush green pasture in the background, with trees dotting the landscape beneath a clear blue sky.

Cottage in Woodstock

4.89 out of 5 average rating, 56 reviews

Globetrotter Retreat - Countryside Carriage House

Newly renovated, fully furnished house in the heart of Vermont countryside, minutes to GMHA, Woodstock village, Okemo Mountain, Killington Mountain, Saskadena Six, Green Mountains, hikes & lakes. Year round outdoor activities. Stand alone private carriage house sleeps 6 people in comfort. Private outdoor dining, propane grill and wood burning firepit. Amazing view of pastures and woods with a rolling brook. Parking for 2 vehicles and space for horse and snowmobile trailers (no animals allowed ).

Top guest favorite

A red barn-style house with a metal roof is surrounded by green grass and trees. A spacious wraparound porch with seating is visible, complementing the inviting exterior. The driveway leads to a gravel path, illustrating a peaceful country setting.

Home in Mount Holly

4.97 out of 5 average rating, 61 reviews

Modern VT Farmhouse w/Hot Tub & Fire Pit

Minutes from Okemo mountain, this family friendly house is the ideal getaway for an adventure in the mountains or a relaxing escape in the woods. Our 4 bedroom home sits on 6 acres of beautiful wooded land. Located right off route 103, you can be at the Jackson Gore entrance to Okemo and on the slopes in 10 mins! (Also, Killington Resort is 12 mi away and Stratton Mountain is 23 mi away.) There are trails nearby for hiking in the warm months and snowshoeing or snowmobiling during winter.

Superhost

A wooden dining table is set with plates and glassware, accompanied by upholstered chairs. Above, a modern light fixture with hanging bulbs provides illumination. A cozy living area with a fireplace and a television is seen in the background, enhancing the communal atmosphere.

Home in Hartford

4.88 out of 5 average rating, 16 reviews

Elegance Meets Rustic Charm: Vermont 3-Bed Retreat

Indulge in tranquility at a pristine Vermont lodge crafted with post-and-beam elegance and a spacious floor plan. This single-family sanctuary boasts ample nooks for games, reading, or unwinding by the wood-burning fire. Ideal for entertaining or relishing moments with loved ones, the home caters to all ages, complemented by a new 6-person spa for relaxing beneath the clear starlit sky. Discover the epitome of a modern retreat in this 3-bed, 2-bath haven, offering an escape for every season.

Top guest favorite

The exterior of a multi-story chalet-style building is framed by lush greenery. The structure features a combination of dark wood and light-colored siding, with multiple windows allowing natural light to filter in. A wide balcony extends along the front, enhancing the inviting atmosphere.

Apartment in Plymouth

4.95 out of 5 average rating, 150 reviews

Moguls Unit:1 mile to F&W Camp w/ HOT TUB

The Moguls Unit is a freshly renovated ground level 2 bedroom apartment at Killington’s Brookside Manor. We are located just 1 mile to lakes and summer camps and 2 miles from Killington’s Skyeship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. If this listing isn’t available for your interested vacation dates, check out our sister listing called the Canyons Unit. We also have a larger 4 bedroom unit (The Ledges) available at this same location too.

Top guest favorite

A yurt with a beige and red exterior is surrounded by lush greenery. A wooden deck leads to the entrance, with comfortable seating visible. The backdrop features trees and an open view of the hillside, illuminated by natural light under a clear blue sky.

Yurt in Randolph

5 out of 5 average rating, 134 reviews

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Superhost

The common area features a large sectional sofa with plaid accents, a wooden coffee table, and a small dining set. Window coverings allow natural light to filter in. A doorway leads to the bedrooms, while artwork decoratively adorns the walls.

Apartment in Pittsfield

4.91 out of 5 average rating, 23 reviews

Clear River Inn - 2 Bedroom Suite

Centrally located on scenic Route 100, the Clear River Inn is the ideal destination for every season. Skiing, snowmobiling, leaf peeping, river tubing, hiking, mountain biking & disc golf are just a few of the various activities all within a 10 mile radius of the property. Home to the Clear River Tavern - VT's true hidden gem, just walking distance from your room. (Closed Mondays & Tuesdays)** **PLEASE NOTE - THE TAVERN WILL BE CLOSED FOR THE SPRING & WILL REOPEN ON MAY 31ST!**

Top guest favorite

A cozy sleeping area features a spacious bed adorned with a colorful quilt and decorative pillows. Natural light enters through two windows with wooden blinds, creating a warm atmosphere. The room is accentuated by a green wall and stylish wall sconces.

Apartment in Sharon

4.98 out of 5 average rating, 57 reviews

Vermont Suite @Anderson-Key Farm

Escape to the Green Mountains for a memorable getaway! Property only 2 miles off I-89 and under 30 minutes to dozens of restaurants & activities. Anderson-Key farm boasts of 20 beautiful acres complete with a pond, brook, farmhouse and barn. The Vermont Suite is a private studio apartment attached to the farm house on one level with beautiful outdoor living and dining space. NOTE: in 2025 the home exterior was changed to gray with updated new siding.

Guest favorite

The historic farmhouse is presented with a welcoming front porch, featuring a mix of seating options. Lush green grass surrounds the home, and mature trees provide shade. The exterior showcases classic white siding and a metal roof, contributing to its charming New England aesthetic.

Farm stay in Hartland

5 out of 5 average rating, 6 reviews

The Spooner House – A Relaxed Farm Stay in Vermont

Nestled in Hartland’s rolling hills, just 20 minutes from Woodstock, the East Wing Suite offers a peaceful escape with modern amenities and scenic views. This private suite includes two bedrooms, two bathrooms, a full kitchen, a cozy reading nook, and exclusive access. Perfect for couples, families, and remote workers, it features high-speed fiber internet, a private entrance, and easy access to Vermont’s best outdoor adventures.

Top guest favorite

The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.

Castle in Clarendon

4.98 out of 5 average rating, 470 reviews

Kingsley Grist Mill, w/ Private Beach & Waterfall

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the history, the romance, the breakfast, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. Come make history with us ! Near Killington & Okemo Mtns.

Guest favorite

The exterior of a spacious three-story home is showcased, featuring a wooden facade with large windows. Flower beds with blooming plants are positioned in front, along with a stone pathway leading to the entrance. A lush green hillside surrounds the property.

Home in Killington

4.9 out of 5 average rating, 135 reviews

Deluxe Suite (Mountain Sports Inn)

This is a 2000 square ft home located right on the Killington Rd leading up to the mountain. This is a 3 bedroom(1 king, 1 queen & 2 twin), 2.5 bath, full kitchen & full living room. Hot Breakfast included Dec-Mid March. Continental Breakfast Included Memorial Weekend-Mid Oct & Mid Nov-Mid April (Message for specifics) Require 2 Night Minimum on most holiday weekends. Quiet Hours: 10pm

Top guest favorite

A cozy bedroom features a spacious bed with a white quilt and decorative pillows. Natural light enters through two windows, illuminating the room's soft blue walls. A bedside table with a lamp is positioned next to the bed, adding functional charm to the space.

Apartment in Chittenden

5 out of 5 average rating, 249 reviews

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont.

Guest favorite

A spacious living area features a modern wood-burning fireplace framed by light brick, with a mounted flat-screen TV above. Comfortable grey sofas and a wooden coffee table are arranged to encourage relaxation, while a wooden staircase leads to the upper level.

Home in Hartford

4.95 out of 5 average rating, 155 reviews

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Relax, rejuvenate, and restore at the Quechee Haus. Located just 10 minutes from downtown Woodstock, 30 minutes from Killington, and around the corner from the family-friendly Quechee Ski Resort, this 3-bed, 3-bath modern retreat offers everything you need for the perfect winter getaway.