Family-friendly holiday rentals in Chittenden

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Top-rated family-friendly rentals in Chittenden

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

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Guest favourite

Guest house in Woodstock

4.98 out of 5 average rating, 206 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

11–18 Dec

$219 SGD per night

Guest favourite

Home in Rutland

4.81 out of 5 average rating, 291 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.

5–12 Sep

$196 SGD per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 114 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

2–9 Oct

$219 SGD per night

Guest favourite

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

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.

8–15 Apr

$173 SGD per night

Guest favourite

Guest house in Granville

4.9 out of 5 average rating, 785 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. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming 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 recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

24–31 Oct

$147 SGD per night

Guest favourite

Guest suite in Royalton

4.96 out of 5 average rating, 166 reviews

Bluestone Farm

Bluestone Farm is a private second story guest suite with all the amenities. High ceilings, quiet, on a Vermont back road with 70 plus acres of land and a pond. You have a full working kitchen; private bathroom with large walk in shower; living room, and private bedroom with a queensize mattress. Nearby to Vermont Law School, 40 minutes to Ben and Jerry's, Woodstock, and Montpelier. 2 miles from Worthy Burger and a quick ride to Interstate 89 for many other Vermont attractions.

1–8 May

$148 SGD per night

Guest favourite

Home in Leicester

4.98 out of 5 average rating, 134 reviews

Luxurious Cottage Massage Therapy Studio On Site

Meticulously clean, private getaway, custom built home to yourself. Beam ceilings, wood floors, oriental carpets, Alexa, grand piano & lots of art. Complete kitchen, pancake mix & Vt maple syrup. Coffee, teas, orange juice, bagels, cream cheese, granola & fruit. Shower bath with shampoo, conditioners, body wash etc. New private deck, tables & chairs... outside art work. Massage available in log cabin on site $70 Ninja Warrior outside gym with trampoline & slack line

5–12 Aug

$254 SGD per night

Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 221 reviews

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

3–10 May

$204 SGD per night

Guest favourite

Home in Rochester

4.97 out of 5 average rating, 182 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

11–18 Nov

$225 SGD per night

Guest favourite

Cabin in Hancock

4.97 out of 5 average rating, 343 reviews

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

26 Mar – 2 Apr

$230 SGD per night

Guest favourite

Flat in Rutland

4.96 out of 5 average rating, 522 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.

6–13 Nov

$138 SGD per night

Guest favourite

Cabin in Warren

4.93 out of 5 average rating, 359 reviews

Cabin in the Woods

This cozy cabin is on a well maintained town (dirt) road a short walk to Blueberry Lake (on National Forest land, non-motorized) and is within 15 minutes of Breadloaf Wilderness Area, Sugarbush Ski Resort, Mad River Glen Ski Area, restaurants and dining, arts and crafts, sports and specialty shops. It's wooded, quiet, has a light open feeling inside.

21–28 Dec

$169 SGD per night