Holiday rentals with breakfast in Windsor County

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.

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.

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.

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!**

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.

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.

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

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.