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!

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.

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.

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.

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 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. Come make history with us ! Near Killington & Okemo Mtns.

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.

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.

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.

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.