Cottage holiday rentals in Woodstock

Casa Rio Loco!

This charming guest cottage affords well appointed privacy while being centrally located in convenient proximity to all the activities the Mad River Valley has to offer. Nestled along a quiet oxbow of our namesake waterway, if you have come for the winter sports you will be a 5/7 minute drive to the Sugarbush base areas, and 10 minutes will bring you to Mad River Glen ("ski it if you can"). Explore the towns of Waitsfield and Warren Village in less than 5... Snowshoeing? Walk out the front door!

The Rustic Cottage, a house built for guests.

In the village there is a wonderful Diner. A Coffee shop, Food Coop, and a delightful Gift Shop. Our General Store, is the oldest continually run general store in Vt. Walking distance to the village and all that is there. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

Kolelemook Cottage!

Kolelemook Cottage - a peaceful lakeside retreat that offers something for everyone all year round. With pristine and shallow water, this lake is perfect for family recreation. We offer an inflatable swim platform, children and adult kayaks, as well as a paddle board for seasonal enjoyment (available Memorial Day-October 15). Board games and Smart TV for indoor entertainment. 10 min. to downtown New London, 20 min. to Sunapee Ski Resort, with loads of hiking options just a short drive away.

Vermont Treehouse - Romantic Private Elegant

3 night minimum, unless prior approval, self checkin. Work remotely. This romantic, elegant, private getaway for two (or one) in our "Treehouse" with sleeping loft, full kitchen & bathroom, screened porch, deck, sauna, WiFi, BBQ grill, etc. Overlooking pasture & mountains. Enjoy the property with 3 miles hiking/snowshoe trails. Guest house on 160 acre private horse farm. Lots to do at nearby ski areas, shopping, hiking, biking, theater in summer. Or just relax. Discount for longer stays.

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.

5 miles from Woodstock-Dog Friendly w/FIOS

Just 5 miles from Woodstock, this bright two-story cottage sits on a peaceful 20-acre oasis of woods, pasture, and hill views. Especially cozy in winter, it’s quiet, warm, and welcoming year-round. The cottage has two bedrooms (queen upstairs, full downstairs), one bath with shower, and an open kitchen/living/dining area. February stays include a warm Arrival Comfort setup and late checkout. Guests using only one bedroom receive a 10% discount, applied after checkout (not combinable).

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

Vermont Hillside Garden Cottage

Cozy converted artists’ studio, tucked in the hills at the end of a country road. Open the French door to views of a sprawling garden and rolling fields, alight with fireflies in the spring and bursting with color in the fall. Warm yourself by the wood burning stove after winter fun or unwind with a local microbrew by the fire pit, listening to the Whippoorwills on a summer evening. Beautiful in all seasons, this modern, comfy cottage is the perfect place to get away from it all.

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Fully Updated, Quiet & Cozy 1-Bedroom Cabin

Escape To Tuckaway Cottage - This perfect-for-two entire cottage is freshly remodeled, clean, comfortable and centrally located for your New Hampshire and Vermont adventures! All new furnishings and fixtures, a fabulous outdoor fire pit, and a wonderful enclosed porch with patio are just a few highlights. A short drive in any direction offers 4-season outdoor recreation with nearby mountains, lakes and rivers, plus dining, culture, and entertainment options abound.

von Trapp Farmstead Little House

Come stay in the beautiful Mad River Valley! Our guest house named the Little House is surrounded by forest and 3.5 miles from the town of Waitsfield. Located on the North East corner of our farmland you'll find yourself less than a mile from our Farm Store where you can stock up on our organic cheeses, yogurts, and meats or beer, wine, and other provisions from over 40 local producers. Enjoy a quiet vacation or a skiing, hiking, biking, or rafting adventure!

The Cottage on Westerdale Road

This charming house is close to the quaint Village of Woodstock, skiing, restaurants and dining, and family-friendly activities. You’ll love my place because of the ambiance, the quality furnishings, air conditioning, the outdoors space, the quiet neighborhood, the comfy beds, and the light. My place is good for couples, business travelers, families (with kids). Sorry, we can no longer welcome pets.