Holiday 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 · Family · Bathroom

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

Value · Location · Nearby

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.

Family · Value · Outdoor spaces

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).

Location · Family · Backyard

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.

Location · Value · Quiet

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 · Heating

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.

Value · Family · Condition

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.

Location · Family · Comfort

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.

Family · Value · Cleanliness

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

Value · Family · Checkout

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 · Family · Cleanliness

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.

Location · Family · Parking