Vacation rentals with breakfast in Windsor County

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!

Value · Location · Sleep quality

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.

Location · Value · Nearby

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).

Family · Location · Cleanliness

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.

Family · Location · Check-in

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.

Value · Family · Kitchen

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.

Location · Value · Quiet

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.

Family · Location · Check-in

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.

Location · Family · Check-in

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.

Location · Value · View

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.

Value · Location · Amenities

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.

Family · Value · Comfort

Vermont private retreat with gorgeous views.

Enjoy and relax at our comfortable home on our spacious deck with an umbrella table, chairs, charcoal grill (in season) and amazing views. Beautiful green lawns, private property only minutes from downtown Bethel, I-89 and the White River. Pets are welcome upon request.

Value · Family · Amenities