Family-friendly vacation rentals in Rutland County

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Top-rated family-friendly rentals in Rutland County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Rutland

4.8 out of 5 average rating, 322 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 462 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

America's only original Grist Mill & Covered Bridge residence, as seen on HGTV's "You Live in What?", (Se.2. ep.1) & worldwide on the Netflix travel series "World's Most Amazing Vacation Rentals" (Se. 2, ep 7). Join us for our 10th season as central Vermont's iconic adult getaway featuring private beach on Vermont's warmest river with tethered, relaxing, float tubes & two private decks overlooking Mill River's secluded waterfall. Come make history with us ! Near Killington & Okemo Mtns.

Guest favorite

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 847 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Guest favorite

Cottage in Pawlet

4.96 out of 5 average rating, 128 reviews

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.

Guest favorite

Home in Mount Tabor

4.98 out of 5 average rating, 242 reviews

Cow Barn Lodge

Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.

Superhost

Bungalow in Castleton

4.8 out of 5 average rating, 318 reviews

Lake Bomoseen Bungalow

My place is nestled on a private road on Lake Bomoseen in the the Lakes Region of beautiful Vermont. We are within 50 minutes from Killington, Pico, and Okemo mountains. Close to Castleton State University, you’ll love the cozy, private, one room guest cottage that awaits you with your very own lake front sitting area a short distance from the bungalow. Use my kayaks or bring your own; dock space available for small boats. Boat rental is an option at a local marina.

Guest favorite

Home in Plymouth

4.95 out of 5 average rating, 236 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favorite

Home in Clarendon

4.95 out of 5 average rating, 266 reviews

Custom 2BR Vacation Retreat in Killington Valley!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Guest favorite

Rental unit in Rutland

4.96 out of 5 average rating, 563 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.