
Family-friendly holiday 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.

Cozy - Killington 40 min. Woodstock-Hanover-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

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Adorable one bedroom studio in 1844 farmhouse.
Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

Apple Blossom Cottage: A Tiny House
The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

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.

Quiet Vermont Farmhouse
Rent a quiet two-bedroom apartment in our 1850's farmhouse in historic Taftsville, Vermont. We are close to the fascinating history, arts, and shopping of Woodstock VT, and near several downhill and cross country ski and snowshoe centers, Marsh-Billings-Rockefeller National Historical Park, and lots of hiking trails, as well as within a short drive of Hanover NH and White River Junction VT. Come enjoy our warm hospitality, wander our gardens, and enjoy our shared patio.

Yurt In The Woods - Come to the Yurt.
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

5 miles from Woodstock-Dog Friendly w/FIOS
Just 5 miles from Woodstock, the Cottage at StillwoodVT is a bright and cozy two-story home set on a peaceful 20-acre oasis of woods, pasture, and hill views. Two bedrooms (queen upstairs, full downstairs), one bath with shower, and open kitchen/living/dining area. Private, quiet, and surrounded by nature. One-bedroom use receives 10% back after checkout (not combinable with other discounts).

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!
Popular amenities for Rutland family-friendly rentals
Family-friendly home rentals with a hot tub

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

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Private Apt. on Farm, Hot Tub with views!

Kolelemook Cottage!

One Bedroom Suite Near Okemo

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Quechee Haus: hot tub, sauna, & mountain views

Secluded tiny house resort - DOG FRIENDLY
Family- and pet-friendly home rentals

The Oaks - secluded rural estate w/ amazing views

Cozy Light-filled Condo in Charming Eastman

Fat Sheep Farm & Cabins - Sunrise Cabin

Private Cabin/PetsOK/Minutes to Okemo/Fast Wifi

Fresh Snow- Luxury Cabin near Ski Areas

Meadow View. 35 acres outside your door!

Historic Home on 17 acres of land. Go escape!

Vermont private retreat with gorgeous views.
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Ranch at Mendon Mt Orchards

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Modern Killington Farmhouse Condo: Close to Resort

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

Pico Great year 1 nite Ok 1 bedrm Ski in Ski out

Hotel Chic - Home Comfort -Ski Easy.
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £183 | £261 | £234 | £165 | £168 | £223 | £261 | £242 | £242 | £260 | £207 | £284 |
| 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 holiday rentals that are family-friendly in Rutland

Total holiday rentals
Explore 60 holiday rentals in Rutland

Nightly prices starting at
Rutland holiday rentals start at £67 per night before taxes and fees

Verified guest reviews
Over 3,360 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Rutland holiday rentals include wifi 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!
Destinations to explore
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- Rentals with a firepit Rutland
- House rentals Rutland
- Rentals with a fireplace Rutland
- Rentals with outdoor seating Rutland
- Rentals with a washing machine and dryer Rutland
- Pet-friendly rentals Rutland
- Rentals with a patio Rutland
- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Squam Lake
- Killington Resort
- Pats Peak Ski Area
- Weirs Beach
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Ice Castles
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Squam Lakes Natural Science Center
- Emerald Lake State Park




