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' .

Ski cottage near Okemo & Bromley *last minute deal

Peaceful centrally located 4 bedroom 3 bath cottage to enjoy any season. Ski-15 min drive (Okemo, Bromley, Magic, and Stratton)15-20 minutes to nearby lakes, hiking, golf,fishing, ATV’s/snowmobiles, visit wineries and breweries. Adventure out go shopping or just have a relaxing time in picturesque Weston. Kick back by the fireplace, take in the beautiful scenery from the covered porch, play on the arcade, make s’mores by the fire pit and enjoy! Make memories with your family and friends today

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.

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!

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.

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.

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

The Smithy Cottage at Consider Bardwell Farm

The historic “Smithy" at Consider Bardwell Farm is the original building used for blacksmithing by Consider Bardwell, himself, in the 1800s. Complete with brand-new, architect-designed kitchen and bathroom, wood-burning fireplace, and stone patio for outdoor grilling and dining, the Smithy is beautiful inside and out. Enjoy meeting our goats and all the local goodies and products that we can stock in your cottage.

Idlewild Cottage on Star Lake Near Okemo

Idlewild Cottage is a tranquil getaway nestled on the edge of Star Lake. The cottage itself provides a peaceful setting for relaxation, while the nearby towns contribute entertainment and establishments to explore. Just 10 minutes to Okemo/Jackson Gore and 30 minutes to Killington, Bromley, and Magic Mountain. 15 minutes to Weston Playhouse and the Vermont Country Store. 45 minutes to Woodstock, VT