Cottage vacation 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' .

Location · Family · Accuracy

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!!

Family · Value · View

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!! We must have your contact information due to local ordinances in case of an emergency. We will ask for that after booking. Between Killington & Okemo 15 minutes.

Location · Family · Checkout

Comfy Cottage w/ Hot Tub in Historic East Poultney

The Cottage is located in historic East Poultney beside the former Poultney schoolhouse, now the local historical society. Enjoy the private hot tub after a day of skiing or exploring nearby Slate Valley hiking and biking trails. Downtown Poultney is just 1 mile away with shops, restaurants, and a pub, accessible by sidewalk directly from the cottage. Pico, Killington, and Bromley Mountains are all under an hour away. Lake St. Catherine is 3 miles away, and Lake Bomoseen is under 10 miles.

Value · Location · Cleanliness

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.

Value · Family · Bathroom

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.

Value · Location · Access

Birch View Cottage - Lakefront Serenity

Welcome to Birch View Cottage on Chipman Lake (aka Tinmouth Pond) in Southern Vermont. Located in the quaint town of Tinmouth, this cottage was completely renovated in the last 10 years. It is 4-season, so it offers summer and winter fun. It's mere steps from the lake, so grab a kayak, canoe or raft and enjoy the water. We offer the use of three kayaks and a canoe. There is a great fire pit right off the deck for smores and in the winter, access to 5 ski areas less than hour away!

Family · Location · Outdoor spaces

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.

Family · Location · Outdoor spaces

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.

Location · Family · Checkout

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.

Value · Family · Walkability

Family or couples retreat on Lake Bomoseen

Newly Renovated! 3 bedrooms 2 baths relax and take in the lake views on the multiple decks. Great for a small family or couples retreat. Boat slip and dock and 100 feet of frontage to enjoy. Bring your boat or kayak or rental. Fully stocked kitchen. Just Bring your SHEETS and TOWELS. Sunsets are great! Lake activities or hiking, biking, horseback riding, all close by. Close to Rutland and Skiing! No large parties or events

Value · Location · Nearby

Pond Cottage at Consider Bardwell Farm

Our newly renovated cottage at Consider Bardwell Farm with huge pond and farmland views awaits visitors looking for a place to escape the daily grind. Located in the Mettowee Valley, Pond Cottage is near ski resorts, hiking trails, and swimming holes. Ideal for all-season sports and shopping. Enjoy meeting our goats as well as enjoying Vermont cheeses, local goodies and produce that we can stock in your cottage.

Value · Location · View