
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.

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.

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.

Quaint 1-bedroom cottage on Blue Ledge Farm
This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

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

Killington Retreat | Deck-Fire Pit-Mountain Views!
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!

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.

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.

Simply Welcoming, Rutland VT
Just 15min from Killington Mountain our apartment is in Rutland City within walking distance to grocery, pharmacy, entertainment, farmers market... Also just steps away from our fabulous local bike path! pinehillpark.org Please Note: the apartment sits on a local business route, at times you can hear cars and the local train.
Popular amenities for Rutland family-friendly rentals
Family-friendly home rentals with a hot tub

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

Ski home to Trail Creek!

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

Scandinavian design Chalet w/ private hiking trail

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

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

Renovated 1BR, Walk to Lifts, Covered parking

SKI ON/OFF Spruce Glen B | Sauna | Fireplace | AC
Family- and pet-friendly home rentals

"Swiss Charm"- A Beautiful Riverfront Chalet

Vermont Hill Top Studio

Ranch at Mendon Mt Orchards

Glamping Cabin with Private Pond and Mountain View

Casita Cabin -Sun drenched cozy cabin on homestead

Farm Stay! - 20 min from Lake George-30 Saratoga

Gristmill Cabin overlooking peaceful brook.

Private Modern Cabin w/View of Fields, Hills
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Renovated unit, prime location! Shuttle on/Ski off

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

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

Epic Views of the Green Mountains

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

One Bedroom Suite Near Okemo

Newly renovated ski retreat at Killington
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $400 AUD | $412 AUD | $344 AUD | $259 AUD | $262 AUD | $260 AUD | $259 AUD | $260 AUD | $268 AUD | $300 AUD | $262 AUD | $376 AUD |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are family-friendly in Rutland

Total holiday rentals
Explore 80 holiday rentals in Rutland

Nightly prices starting at
Rutland holiday rentals start at $91 AUD per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Rutland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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 United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Lake George Expedition Park
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Dorset Field Club
- Whaleback Mountain
- Fox Run Golf Club
- Autumn Mountain Winery
- Willard Mountain
- Ekwanok Country Club
- Mount Sunapee Resort
- Montshire Museum of Science




