
Family-friendly vacation rentals in Rutland
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Top-rated family-friendly rentals in Rutland
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Mi Casa es su Casa!
Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

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.

Cozy Contemporary Downtown Texaco
Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

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.

Mountain View Apartment
Quiet, second floor, farmhouse apartment in country setting. Two connected bedrooms sleep four, one with a queen bed and the other with two twin beds. Watch the sunrise from the private deck or walk the fields to watch the sun set over the Adirondaks. Plenty of room to roam over the farm fields. Forty minutes to ski areas, less to nearby lakes or Castleton University. Owner on property. -18 mi to Killington Resort/ 15 mi to Pico Ski Resort -9 miles to Rutland Regional Medical Center

Apartment in Vermont Historic Home
This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

River House Apartment - Dog friendly
Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Baby Queens Barbie-core Studio Apt (dog friendly)
Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

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, skiing, golf, 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.

Cozy Poultney Village Apartment
I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Serene Bus Getaway Among Rolling Farm Land
Tucked off a quiet dirt road, this stationary bus promises to provide you and yours an unforgettable accommodation for your next Upstate NY retreat. Come stay in the Sleepy Tire, and wake up to beautiful views of Vermont’s Green Mountains, an indoor bathroom with flushing toilet and hot shower, and WiFi so you can stay connected to those that matter.

Castleton Cottage
This is a newly renovated first floor one bedroom apartment. It has all the amenities of home including a walk-in shower, full kitchen, and a pull-out sofa. It is within walking distance of Lake Bomoseen and its many amenities, including boat rentals and creemees. This is a non-smoking unit. Please let us know if you have any questions.
Popular amenities for Rutland family-friendly rentals
Family-friendly home rentals with a hot tub

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

Killington/Okemo, 7p Hot tub, Spacious, Mtn.views!

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Beautiful Spacious Condo at Killington Resort

Private Barn On a Hilltop in Fairlee, Vermont

Waterfront 1-bedroom apartment on 5 acres

Rustic and Cozy Vermont Getaway at Sugarwood Cabin

Private Ski Cabin On Okemo Mt. With New Hot Tub!
Family- and pet-friendly home rentals

Cabin on the Hill

Ranch at Mendon Mt Orchards

Lower Yurt Stay on VT Homestead

Runamuk Farm

Glamping Cabin with Private Pond and Mountain View

The Guest House at Sky Hollow

Cozy Home in Poultney, Vermont.

Beautiful 1 Bedroom Suite with private entrance
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

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

Epic Views of the Green Mountains

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

South Tree House Retreat of Lake George

Newly renovated ski retreat at Killington

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

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Quick stats about vacation rentals that are family-friendly in Rutland
Total rentals
80 properties
Nightly prices starting at
€ 51 before taxes and fees
Total number of reviews
3.9K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi
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- Family-friendly rentals Rutland County
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- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Lake George Expedition Park
- Dorset Field Club
- Hooper Golf Course
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Montshire Museum of Science
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Ekwanok Country Club
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Mount Sunapee Resort