
Family-friendly holiday rentals in Rutland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Rutland
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Cottage for Two/Solo Getaway/Musician's Retreat
Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Private Riverside Studio* Upper Valley*Vermont
This unique place has a style all its own. Perfect for a traveling nurse or anyone who needs a relaxing getaway or a remote place to work. This studio apartment has river and garden views and is conveniently located in the New England Village of North Hartland. A 15-20 minute drive to Dartmouth College or DHMC. Take country walks across the twin covered bridges right from your doorstep. Relax on the front porch and watch the bald eagles and peregrine falcons search for prey along the river.

Adorable Dog Friendly Cottage w/FIOS
Bright and clean 2-story cottage on a 20-acre oasis. 10% off for guests using only one bedroom (cannot be combined with other discounts). Details in property description. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bath (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. For groups or more space, view my other listing located on the same acreage: airbnb.com/h/hartlandvacationhome

Newly renovated private space on Ascutney Trails
Newly renovated private space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, Maple Kitchen Restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Air conditioned during the summer. Television and fast wifi.

Private Modern Cabin w/View of Fields, Hills
Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

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.

Cabin on the Hill
Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Off Grid Tiny House
This sweet little house is great for those who want to get away from it all. It's like camping but with many more creature comforts. Hot and cold running water and a fantastic hot outdoor shower! The house does not come with sheets and towels but if you need that, please let me know and I’ll make that happen for a small fee ($15)! Great for kids! Plenty of mountain biking and hiking from your front door. Lots to explore. Nature right outside your door! 10% veteran discount.

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.

Yurt In The Woods - Private Refuge
The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Renovated 1817 Hobby Farm Close to Dartmouth
Come stay at PRIVATE GUEST QUARTERS on our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

Lovely Treehouse Stay at Wise Pines- NoBo
Wise Pines is a Holistic & Sustainable Inn/Hiker Hostel that offers a unique farm experience. Reconnect with nature at this bedroom on stilts allows you to sleep amongst the trees peacefully. Farm stand food is available seasonally and yoga is available upon request. Explore 40 acres of walking trails through the woods, garden and around a tranquil pond.
Popular amenities for Rutland family-friendly rentals
Family-friendly home rentals with a hot tub

Dog heavenly! Private, beautiful and relaxing.

Scandinavian design Chalet w/ private hiking trail

Lower Yurt Stay on VT Homestead

Renovated 1BR, Walk to Lifts, Covered parking

Hot Tub Farmhouse - Buttercup Studio - Jamaica VT.

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Private Barn On a Hilltop in Fairlee, Vermont

Quechee Hathaway House: hot tub, sauna & views
Family- and pet-friendly home rentals

Convenient and chic private suite with 2 bedrooms!

The Oaks - secluded rural estate w/ amazing views

Newport Jail “Break”

Fat Sheep Farm & Cabins - Sunrise Cabin

The SugarMaple Treehouse @ Vermont ReTREEt

Adorable one bedroom studio in 1844 farmhouse.

Sunday Mountain Surprise

Stylish Ascutney Cabin with Mountain Views
Family-friendly home rentals with a pool

Comfy ski in/out studio at base of Pico-Killington

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Epic Views of the Green Mountains

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

Beautiful Spacious Condo at Killington Resort

Newly renovated ski retreat at Killington

SKI ON/OFF Spruce Glen C | AC | Sauna| Fireplace

1 night Ok at the base of Pico 1 bedrom Ski in out
Quick stats about holiday rentals that are family-friendly in Rutland
Total rentals
50 properties
Nightly prices starting at
$157 NZD before taxes and fees
Total number of reviews
3.3K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
50 properties include access to Wi-Fi
Destinations to explore
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- Rentals with outdoor seating Rutland
- Rentals with a washing machine and dryer Rutland
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- House rentals Rutland
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- Rentals with a fireplace Rutland
- Pet-friendly rentals Rutland
- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Squam Lake
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Weirs Beach
- Owl's Nest Resort
- Monadnock State Park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Brattleboro Ski Hill
- Fox Run Golf Club
- Ekwanok Country Club