Vacation rentals with breakfast in Windsor County

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Top-rated breakfast rentals in Windsor County

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

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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, 53 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

The exterior of the house is illuminated at night, highlighting its spacious wraparound porch and large windows. The well-manicured lawn gently slopes down, with stone pathways leading to the porch. Nearby, a vehicle is parked, nestled in a serene, wooded environment.

Home in Mount Holly

4.97 out of 5 average rating, 58 reviews

Modern VT Farmhouse w/Hot Tub - 10 mins to Okemo

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

Home in Hartford

4.87 out of 5 average rating, 15 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.

Guest favorite

A hot tub is situated under a wooden gazebo, with views of a snow-covered chalet in the background. The exterior features traditional black and white architecture, framed by tall trees. The sky appears bright blue with scattered clouds.

Chalet in Plymouth

4.95 out of 5 average rating, 118 reviews

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

The Ledges Unit at Killington’s Brookside Manor is a freshly renovated home away from home just 2 miles from Killington’s Skyeship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. The Ledges is a 2 story chalet in a 4 unit building. The 1st floor has a kitchen, living room with a large stone mantel and wood stove, dining room, and full bathroom. The 2nd floor has 4 bedrooms and bathroom. The other 3 listings at this location are rented separately.

Top guest favorite

Yurt in Randolph

5 out of 5 average rating, 129 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 exterior of Clear River Inn is displayed, featuring a three-story building with a modern design and solar panels on the roof. A prominent sign indicates the tavern's location around back. The surrounding landscape includes green hills under a clear blue sky.

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!**

Guest favorite

The exterior of a two-level barn is seen, featuring a red metal roof and a wooden upper deck with two chairs. A staircase leads up to the deck, surrounded by autumn leaves on the ground. Trees and a gravel path are visible in the background.

Barn in Hartland

4.87 out of 5 average rating, 23 reviews

Renovated Barn Stay at Wise Pines

Wise Pines is a Holistic & Sustainable B&B/Hiker Hostel that offers a unique farm experience. In the rural woods of Vermont, this two level renovated barn offers two private rooms, each with queen beds and a bunk room of 8 beds (4 bunks) with a small seating area and a large upper deck that over looks the property. The barn sits on 40 acres of land, complete with walking/hiking trails and a pond to sit by and enjoy. The owners live on property with their dogs, goats & chickens.

Top guest favorite

A tranquil scene depicts a farmhouse surrounded by lush greenery, reflecting in a calm pond. Flanking the water are tall grasses and ferns, creating a serene natural frame, while trees provide shade and enhance the rural charm.

Apartment in Sharon

4.98 out of 5 average rating, 53 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, experiences and outdoor activities! Complementary Concierge services available. 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.

Top guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 465 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

A modern wooden structure features numerous large windows that invite natural light. A spacious balcony extends from the upper level, overlooking a snowy landscape. Surrounding trees create a serene environment, complementing the home's rustic aesthetic.

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

Guest favorite

Farm stay in South Royalton

4.84 out of 5 average rating, 216 reviews

Corncrib Tiny House Glamping Cabin

Queen-sized bed in historic corncrib cabin in the heart of Vermont with gorgeous views of fields and forest. We also have several other rooms available. The tiny house comes with a queen sized bed in the loft. It has a private full bathroom with clawfoot tub and shower, tiny living room, dining area and full kitchen. It can accommodate one or two people.

Top guest favorite

A rustic red shed is situated in a landscaped area surrounded by trees. Four green Adirondack chairs are arranged around a stone fire pit, creating an inviting space for outdoor gatherings. The lawn is well-kept, providing a serene setting.

Apartment in Chittenden

5 out of 5 average rating, 248 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.

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What guests are saying

The Spooner House – A Relaxed Farm Stay in Vermont

5 out of 5 average rating, 3 reviews1 week ago

We had a wonderful stay! Our hosts were incredibly kind and welcoming. It truly felt like visiting old friends. Their warmth made the space feel like home from the moment we arrived. One of the highlights was spending time with Pinky the cat, who quickly became everyone’s favorite companion. Not to mention the awesome coffee/espresso machine! The setting was peaceful, the home was clean and comfortable, and the whole experience was exactly what we needed. Would absolutely stay here again!

Farm stay in Hartland

What guests are saying

Elegant Spacious Private Suite

5 out of 5 average rating, 87 reviews3 months ago

We had great time at Sheila’s place, everything was perfect from the beginning to the end. House and surroundings were beautiful and peaceful, and specially after long day skiing on the mountain. Thank you so much for your hospitality! We will definitely comeback when visiting Vermont soon.

Private room in Hartford

What guests are saying

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

5 out of 5 average rating, 50 reviews1 month ago

Sabrina's house was in a great location for our Killington Ski Trip. It comfortably fit a large group of us and the hot tub was a welcome bonus after a long day of skiing. There was an issue with water pressure and pipes freezing because of another tenant in the building leaving a door open, but the host was very responsive and fixed the problem immediately. We would definitely stay at this house again!

Chalet in Plymouth

What guests are saying

Okemo 3BR Available

5 out of 5 average rating, 3 reviews37 months ago

We had a wonderful stay at Adam’s house with our teen boy and several friends. It’s a spacious townhouse style condo. Kids slept in the bunk room and there were two additional small bedrooms on the lower level next to the bunk room. We slept in the master bedroom which is sort of like a loft although it has a door - but not sound proofed from the main TV area. We cooked several meals in the well equipped kitchen. Adam was responsive and helpful during our stay. Big TV, comfy couch, lots of games. It’s an easy five minute drive to drop skiers off at Okemo. Hot tub worked well. Great for a family ski weekend.

Townhouse in Ludlow

What guests are saying

Beautiful winter cabin near Jackson Gore

4.74 out of 5 average rating, 243 reviews1 month ago

We stayed here to ski at Killington & it was a great spot for a small group. Super close to Okemo if you're looking to ski there and around the corner from Shaw's for groceries. The house itself was super clean, cozy & comfortable. Would definitely stay here again.

Cabin in Ludlow