
Family-friendly vacation 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.

90 Day or Weekend Rentals GREAT Piano!
Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

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.

Clean, cozy, beautiful studio in the heart of WRJ.
This beautiful studio is in a new building built in 2021. It is a clean, quiet, place to stay in a building of young professionals. Walking distance to restaurants, bars, art galleries, and all this historic town has to offer. Within a 3-min walk: Tuckerbox, Wolf Tree, Big Fatty’s, Northern Stage. 10 min: King Arthur Baking 10 min: Dartmouth College 15 min: Dartmouth Hitchcock Medical Center 25 min: VT Law School Perfect, cozy place for visiting parents, traveling nurses, professionals, etc.

The Old Farmhouse
This is a farm house style lodging with the apartment as seen,on the second floor accessible with stairs. Bathroom with stand up shower. A furnished Kitchen. 2 Bedrooms with queen beds. There is Wifi ,TV, and a work table. Located in the heart of the Upper Valley. In town on the Main Street. We are 5 miles to Dartmouth College and Hospital. Close to retail,restaurants. We have been vaccinated , boosted, would like to remain contact-free when possible. We are available if you have questions.

Sunny Side Airbnb (dog friendly)
Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

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.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

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.

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

Addie's Place
A cozy and quiet space close to Dartmouth College (8 mins), Dartmouth Hitchcock Hospital (12 mins), and White River Junction Center (5 mins). You will have a private entrance to the space and access to a yard, a 3 season patio room, bedroom with a queen sized bed and queen pullout couch, a separate dining area, grill, and a private bathroom. There is no kitchen but there is a mini fridge, table, coffee/tea bar, plates, utensils, mugs, and a microwave.

Bog Mt Retreat Upstairs Suite
A unique crafty cozy 1 bedroom/1 bathroom upstairs suite with most of the comforts of home. Woodland trails on the property, moderate hikes nearby or bring your kayaks and explore the many ponds and lakes in the area. Ragged Mt and Mt Sunapee Ski Resorts are both under 30 minutes away. This newly designed suite is perfect for an individual or couple wanting to escape into the country but still be within an easy driving distance to local sites.
Popular amenities for Rutland family-friendly rentals
Family-friendly home rentals with a hot tub

~The ClubHaus~

Cozy Bow House Perched in Trees w/ Hot Tub & View

Scandinavian design Cabin w/ private hiking trail

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Private Barn On a Hilltop in Fairlee, Vermont

Quechee Haus: hot tub, sauna, cold plunge, & views

Secluded tiny house resort - DOG FRIENDLY

Newly renovated private space on Ascutney Trails
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”

Rustic Cabin Retreat

Apartment on Main Street

Sunday Mountain Surprise

Private Tiny House Retreat

Meadow View. 35 acres outside your door!
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Ski home to Trail Creek!

Epic Views of the Green Mountains

One Bedroom Suite Near Okemo

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

Newly renovated ski retreat at Killington

Serene Top Floor Condo (resort style amenities)
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$51,445 GYD | G$73,194 GYD | G$65,666 GYD | G$46,217 GYD | G$47,054 GYD | G$62,529 GYD | G$73,194 GYD | G$67,966 GYD | G$67,966 GYD | G$71,521 GYD | G$45,381 GYD | G$57,719 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
Quick stats about vacation rentals that are family-friendly in Rutland

Total vacation rentals
Explore 50 vacation rentals in Rutland

Nightly prices starting at
Rutland vacation rentals start at G$18,821 GYD per night before taxes and fees

Verified guest reviews
Over 3,310 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Rutland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Rutland rentals

4.9 Average rating
Rutland stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Windsor County
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- Family-friendly rentals United States
- Stratton Mountain
- Squam Lake
- Okemo Mountain Resort
- Sugarbush Resort
- Monadnock State Park
- Stratton Mountain Resort
- Weirs Beach
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Crotched Mountain Ski and Ride
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Dorset Field Club
- Whaleback Mountain
- Fox Run Golf Club
- Autumn Mountain Winery
- Ekwanok Country Club




