Cottage holiday rentals in Rutland County

Private cottage in the woods

Maple Cottage - a safe place for everyone - bright, 700sf on 36 hilly, wooded acres in the Green Mountains. Winter lake and mountain views from the great room. In summer, you are nestled in the trees, but a nearby deck provides amazing lake views. Quiet and private, close to everything - restaurants, galleries, shops, winter & summer activities on the lake or the ski hill. A digital guide to the house and area available after booking. Questions? Scroll to the bottom and click 'Message Host' .

Charming Mountain Cottage **NO CLEANING FEE**

Enjoy a charming cottage on the side of a hill in beautiful Weston, Vermont. You'll have the entire building to yourself (it's a stand-alone structure) to come and go as you please. My goal is to provide a five-star experience for five-star guests. I think little details like Ralph Lauren bath sheets, freshly-pressed bed linens, and duvet covers that are laundered between each guest make a difference. If you agree, you're probably the type of guest I'd enjoy hosting! Motorcycle friendly!!

The Cottage in East Poultney

The Cottage is located in historic East Poultney next to the old Poultney schoolhouse (now historical society). Just over 1 mile to the town of Poultney. The sidewalk starts (or ends how you look at it) in front of the cottage which leads to town. Great for a walk or bike ride. Pico, Killington and Bromley Mountains all less than an hour drive. Plentiful fishing and boating opportunities. 3 miles to Lake St Catherine, under 10 miles to Lake Bomoseen. Slate Valley bike trails surround the area.

Bright & Homey 3 bedroom near Killington & Pico

Cozy and well equipped three bedroom on a property with 40 acres of woods, and trails for hiking, snow shoeing, and cross-country skiing. Another rental property sits at the end of the driveway. Huge old pine trees and mowed fields create space and privacy between the two. With this rental comes the use of 4 kayaks, a grill, walking poles, and a huge porch excellent for watching for bear or moose! Big windows throughout the house let in lots light. New mattresses assure your restful sleep.

Newly Renovated, Hot tub, 2min to Killington lift

Stone’s Throw Vermont is a 3 bed/1.5 bath cottage with hot tub, fireplace, and space for 6 guests conveniently located in central Vermont. Placed right on the US-4 corridor; you’re 2 minutes from the Killington Ski Resort’s Skyship Ski Gondola escorting you to the world class amenities of Killington Resort, 5 min from the best craft beer in the region at Long Trail Brewery, 10 min to Echo Lake, and 20 min from the shops and cafes of Woodstock, VT. Truly everything is a Stone’s Throw away.

Carriage Barn at Indian Hill

Our guest cottage is a lovely converted 1840s-era carriage barn nestled in the heart of the Mettawee Valley in the southwest corner of Vermont. It is decorated with antiques, artworks and an upright piano. Our 65 acres on scenic Indian Hill are available for hiking & snow-shoeing. We have 12 acres frontage on the Mettawee River, rated one of the best for fly fishing in VT. Ready access to many area attractions, from local swimming holes to skiing at nearby Bromley and Stratton mountains.

Cottage on Lake St. Catherine, MTN Biking/Hiking!

Charming Two Bedroom Cottage. Explore Lake St. Catherine using complimentary canoes or kayaks, or just enjoy the view. Access the extensive Slate Valley trail system by bike, or drive a short distance to any of the many trailheads. A short drive or paddle lands you at Lake St. Catherine state park, where you can hike, mountain bike, or explore the new disc golf course. You can also enjoy a very scenic game of golf at the Lake St. Catherine Country club, just 1.5 miles down the road.

Lake Saint Catherine Cottage with private Dock.

Visit this charming lake cottage anytime of the year. Enjoy an early morning kayak (we have two that you can borrow) and listen to the loons calling. Fish from the end of the dock, swim out to our big yellow raft to sunbathe. An 18 hole golf course is around the corner. Hike nearby trails. Dine al fresco on the patio or deck after grilling your favorite catch. We are well stocked with games, books and there is A/C but we like to feel the breeze come through windows off the lake!!!

Cute Cabin! Plymouth, Vermont.

Hot Tub~Fire Pit~Dog-Friendly~Screened-In Porch~Outside Shower~Fireplace~Private Beach & Docks~Boats~Lake view~Waterfowl~3BR & 3BA~ We provide generous premium amenities, including fine linens, plush towels, toiletries, high-end cookware, grills, and a clean, well-stocked, and organized spice cabinet. We provide better & more!! Rates include all cleaning. Plus VT tax. Airbnb adds Airbnb's booking fees. Rustic charm. Modern amenities. Between Killington & Okemo 15 minutes.

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Family or couples retreat on Lake Bomoseen

Newly Renovated! Now 3 bedrooms 2 baths and relax and take in the lake views in the new decks. Great for a small family or couples retreat. Boat slip and dock and 100 feet of frontage for your use on the lake. Fully stocked kitchen. Just Bring your SHEETS and TOWELS. Sunsets are great! Lake activities or hiking, biking. We are year round! 20 Mins from Rutland, 30 Mins. from Skiing! Please bring your own boat or kayak otherwise rent No large parties or events

Ludlow Village Guest Cottage with Prime Location

Renovated one bedroom, one bath guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entrance to Okemo Base Lodge. Anything you need can be found a short walk from the front door including a wide variety of restaurants, shops and bars for Après Ski. Sitting on the weekend and holiday shuttle route to Okemo, its the perfect spot to be! Cottage has a fully equipped kitchen and wifi for your technology needs.