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Vacation rentals with breakfast in Windsor County

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Top-rated accommodations with breakfast in Windsor County

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

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Guest favourite
A colorful sign for Clear River Inn is prominently displayed, featuring details about the tavern located at the back. The surrounding area includes greenery and flowering plants, with scenic hills visible in the backdrop under a bright blue sky.
Apartment in Pittsfield

Clear River Inn - 2 Bedroom Suite

Live the "Suite Life" at the Clear River Inn in this spacious 2BR, 1-bath suite. Featuring 4 beds between 2 large bedrooms separated by an open kitchen, dining, and living area - this suite perfect for keeping the crew together, or if you just want bragging rights for booking THE spot. Centrally located on scenic Route 100, minutes from skiing, snowmobiling, hiking & more. Enjoy the daily Breakfast Nook & unwind at the Clear River Tavern Weds–Sun, just steps away. Free disc golf course onsite!

4.92 out of 5 average rating, 26 reviews
Top guest favourite
Home in Mount Holly

Luxe Farmhouse Mins to Okemo - Hot Tub & Fire Pit!

- 9 min to Jackson Gore at Okemo; 25 min to Killington - 8 seat Jacuzzi hot tub - Solo Stove for Apres Ski S'mores - Gear Dryer in the mudroom to air out all your ski gear - Grill on the deck for a night cooking in - Coffee/cocktail station w/ Keurig coffee maker - Arcade machine with over 3,500 games - Sonos speakers by the hot tub and in the kitchen/living room area - Towel warmer by the hot tub - Great sledding hill in the side yard - Wrap around porch with sunset views - Two car garage

4.95 out of 5 average rating, 85 reviews
Top guest favourite
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

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.

4.99 out of 5 average rating, 163 reviews
Top guest favourite
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

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. Private outdoor dining, propane grill and seasonal wood burning firepit. Amazing view of pastures & woods with a rolling brook. Parking for 2 vehicles & space for horse and snowmobile trailers (no animals allowed).

4.92 out of 5 average rating, 78 reviews
Superhost
A living area is showcased, featuring a stone fireplace as a focal point. Comfortable wooden seating arrangements are present, with a coffee table displaying decorative items. Large windows allow natural light, offering views of the outdoors, while a subtle beige carpet adds warmth to the space.
Cabin in Killington

The Chalet at The Snowed Inn

Keep it simple at this peaceful and centrally-located place. The Chalet is a separate unit located at The Snowed Inn, a 5-star Inn in Vermont, offering 2 floors - top floor is large studio space with bed, couch, kitchen, jacuzzi tub, fireplace, balcony. Bottom floor offers pull out couch with large screen TV. The Inn offers complimentary breakfast, 24 hr coffee/tea & outdoor hot tub. Enjoy sitting at the bar and choose from our wine/beer list and pub menu. 1 mile from Killington Mt.

4.83 out of 5 average rating, 24 reviews
Top guest favourite
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

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 18 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 outdoor living, gas fire pit, and dining space. NOTE: in 2025 the home exterior was changed to gray with updated new siding.

4.97 out of 5 average rating, 93 reviews
Top guest favourite
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

Kingsley Grist Mill Waterfall & Private Beach OMG

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 romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

4.98 out of 5 average rating, 516 reviews
Guest favourite
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

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.

5.0 out of 5 average rating, 30 reviews
Top guest favourite
Apartment in Clarendon

Trestle Farm

Trestle Farm, formerly a 50-year old horse rescue ranch, which we are transforming into a floriculture farm. 12 acres of open meadows to enjoy. If you’re looking for a bit of old, rustic Vermont, Trestle Farm offers all you need for a peaceful getaway, and yet it is just minutes to Rutland. With over 30 years of estate caretaking experience we welcome you to Trestle Farm to share this special Vermont hideaway.

4.98 out of 5 average rating, 97 reviews
Guest favourite
A wooden porch is framed by weathered gray walls, leading to a solid wooden door. A small bench sits nearby, while a potted plant with white flowers adds a touch of greenery to the rustic setting.
Farm stay in South Royalton

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.

4.84 out of 5 average rating, 226 reviews
Top guest favourite
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

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.

5.0 out of 5 average rating, 289 reviews
Top guest favourite
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

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.

4.96 out of 5 average rating, 178 reviews

Popular amenities for Windsor County accommodations with breakfast

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with breakfast

Home in Ludlow

Ludlow Village on Shuttle Rte w/Infrared Sauna

5.0 out of 5 average rating, 4 reviews
Home in Killington

The Summit Cottage, Killington | 2BR/2BA Sleeps 6

A spacious living area features two comfortable sofas adorned with decorative pillows, complemented by a coffee table on a patterned rug. Large windows allow natural light to fill the space, and a striking wall art piece is displayed above the seating.
Home in Chittenden

Resort Property near Killington

The exterior of a modern home is framed by lush greenery, featuring a stone pathway that leads to the front door. Planters with flowers are positioned near the windows, and a pair of light green chairs sit on the porch, inviting relaxation.
Home in Hartford

Renovated home close to Dartmouth College and DHMC

4.33 out of 5 average rating, 3 reviews
Top guest favourite
A green farmhouse is framed by lush, flowering gardens, featuring tall grass and vibrant irises. Warm light glows from the windows, creating a welcoming sight amidst the natural surroundings. A decorative horse statue adds charm to the entryway, inviting guests to explore further.
Private room in Woodstock

Studio Apartment in Beautiful South Woodstock

4.97 out of 5 average rating, 145 reviews
Top guest favourite
A cozy living area features a wooden spiral staircase leading to the upper level. A stone fireplace serves as the focal point, flanked by large windows allowing natural light. Comfortable seating includes a striped sofa and a plush black throw, with a wooden coffee table centered on a soft rug.
Private room in Mendon

Private fireplace suite & luxury bath - Killington

4.99 out of 5 average rating, 835 reviews
Top guest favourite
An upstairs room features a cozy seating area with a stylish black chair and a small red table. A wooden dresser with rounded edges complements the light-colored walls. A plush carpet adds warmth to the space, and a window allows natural light to enter.
Private room in Andover

Finnish Farmhouse with Private Rooms

5.0 out of 5 average rating, 44 reviews
Guest favourite
The exterior of a two-story home is visible, featuring a symmetrical façade with large windows and a round decorative window. Surrounding greenery and a gravel driveway can be observed, contributing to the tranquil setting.
Private room in Hartford

Mountain and Valley Views 1A

5.0 out of 5 average rating, 18 reviews

Apartment rentals with breakfast

Guest favourite
Private room in Killington

Premium Suite (Mountain Sports Inn)

4.85 out of 5 average rating, 52 reviews
Top guest favourite
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

Vermont Country Suite

5.0 out of 5 average rating, 289 reviews
Top guest favourite
Apartment in Clarendon

Trestle Farm

4.98 out of 5 average rating, 97 reviews
Top guest favourite
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

Vermont Suite @Anderson-Key Farm

4.97 out of 5 average rating, 93 reviews

Bed and breakfast rentals with breakfast

Superhost
The charming two-story Vermont cape house is enveloped in lush greenery and blooming wildflowers, creating a picturesque setting. The exterior features a brown roof with dormer windows and a welcoming porch, nestled under a bright blue sky with scattered clouds.
Private room in West Windsor

Thorny Hills Farm

4.85 out of 5 average rating, 110 reviews
Top guest favourite
A spacious house sits nestled among trees, showcasing large windows that provide ample natural light. A deck with an umbrella overlooks a well-maintained lawn. The scene is set against a backdrop of colorful foliage and a sky painted with soft clouds.
Private room in Bridgewater

MT Retreat / Killington, Woodstock, Rutland, Okemo

4.99 out of 5 average rating, 182 reviews
Guest favourite
The historic 1840 property features a white exterior with black shutters and arched windows. An American flag is displayed prominently. The well-maintained lawn is adorned with fallen autumn leaves, and a covered porch is visible, inviting guests to enjoy the scenic surroundings.
Private room in Barnard

The Fan House Vermont Country Home

4.91 out of 5 average rating, 94 reviews
Top guest favourite
A spacious bedroom features a four-poster bed dressed in white linens and plush pillows. Two bedside tables with lamps flank the bed. A round mirror hangs above a chair beside a small table, while a plush area rug lies underfoot. Windows are adorned with drapes.
Private room in Chester

Farm at Williams River House - Essex Suite

5.0 out of 5 average rating, 44 reviews
Guest favourite
The exterior of a vibrant red building is displayed, featuring multiple stories and architectural details such as white trim. Snow covers the surrounding ground, and a light dusting is present on the roof. A paved driveway leads to a parked vehicle, and a whimsical yellow structure adds a pop of color.
Private room in Weathersfield

The Oak Room - Ladoga

4.94 out of 5 average rating, 63 reviews
Guest favourite
The historic Windsor Mansion is situated atop a gentle hill, surrounded by lush greenery and trees in various shades of green. The white exterior of the mansion stands out against the natural backdrop, with many windows reflecting the sky above.
Private room in Windsor

Stay at the largest Colonial Revival Mansion in US

4.89 out of 5 average rating, 93 reviews
Guest favourite
A historic brick home is presented, featuring a centrally located entrance flanked by large windows. The white picket fence and stone pathway lead to the inviting front door. The house is set within a landscaped yard, showcasing a blend of greenery and elegant architectural details.
Private room in Norwich

The Partridge House Room 201

4.93 out of 5 average rating, 178 reviews
Guest favourite
A historic brick building is framed by verdant trees and a white picket fence. The entrance features large windows and shutters, with a flag displayed prominently. A sign indicating the property name is visible by the pathway, contributing to the charming exterior.
Hotel room in Tunbridge

Hubble Shire Farm French Queen Suite

5.0 out of 5 average rating, 40 reviews

Destinations to explore