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

Private constructed yurt on organic farm
Take it easy at this unique and tranquil getaway. The entire constructed yurt is yours to enjoy privately. Nestled on an organic farm, it sits a bit above Bristol offering sweeping views of the valley and the beautiful Adirondack mountains. There are many farm animals on the property and farm tours are available upon request. PLEASE NOTE: The queen bed is only accessible by a ladder. The property is located up a steep driveway. During the winter months all wheel drive vehicles are required.

Charming one bedroom just minutes to Middlebury!
Just minutes away from Middlebury College, this well designed 1 bedroom is the perfect place for a stress-free getaway! Great location for parents to stay when visiting their Midd kids. The renovated apartment is well appointed with central heating/AC, super fast WiFi, laundry machines, full kitchen, full en suite bathroom with bath and shower, brand new queen bed and mattress, a great room with dining, cozy seating, and a 65" smart TV. This clean and tidy unit is the definition of easy living.

Welcoming Retreat Near Middlebury & Lake Dunmore
Come swim, hike, or ski while staying at our welcoming and comfortable 2nd floor studio apartment with plush linens, comfortable King bed, a well equipped kitchenette plus space to relax, work & play. + Garage parking. -Single Family home also now available as1 or 2 BRs 7 min from Middlebury with all its amenities 5 min from Lake Dunmore 13 min from Brandon 16 min from Rikert Outdoor Center for cross country 18 min from Snowbowl for down hill skiing 32 miles - approx 50 mins from Killington

Bristol Cozy Yurt near Hiking/Foliage|MapleFarm
Our cozy yurt is located within minutes of amazing, hiking, biking, skiing, breweries and much more! Relax around the fire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking and swimming skiing in Central Vermont. Mt Abe and Bartlett's Falls are the closest options. We're also close to civilization with several towns close by to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

Bluebird Studio- Light filled and airy
This studio apartment attached to the main house has a style all its own. Contemporary design with high ceilings, clerestory windows and a skylight. Spaces include a large Living Room/Bedroom, Kitchen/Dining area, bathroom with a step-in shower and an adjoining Dressing Room with vanity and sink. There is also an outdoor covered space to enjoy. Furniture includes a Queen size bed, 3 comfy chairs, small round table and 4 chairs. Location is a bit more than one mile from downtown Middlebury.

Breadloaf Hut. Glamping, hiking, biking, foliage
Hiker, writers’, gravel/mountain biker's paradise! Our quiet glamping retreat provides easy access to miles of wilderness. The hut has a cozy bed, kitchenette, and camping basics making for an easy and cozy getaway. Follow a trail to the Catamount Trail or drive a few minutes to the Long Trail. Enjoy miles of gravel biking from the door or go to Moosalamoo or Rochester for prime mountain biking trails. In the evening, sit on the deck under a blanket of stars and warm your toes by the fire.

The Cottage Apartment in downtown Middlebury.
This charming, 1st floor two-bdr. cottage apartment is steps from Main Street, downtown Middlebury, & walking distance to shops, restaurants, and the College. An historic college town, Middlebury is replete with great restaurants, shops and cultural events to enjoy, all within walking distance. The comforts of this home include private parking, gardens, separate entrance, full kitchen and bath, and sleeps four. It is only a half hour from The Middlebury College Snow Bowl, and Lake Champlain.

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.

Hilltop Cottage With a View
Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

Home Suite Home in Cornwall, Minutes from Midd!
Looking for a home away from home on your travels in the Champlain Valley? Whether you're searching for a place to lay your head while visiting your Middlebury College student, a home base while exploring the gorgeous Green Mountain State, or a secluded, peaceful retreat in which to write the next chapter of your book, we've got just the spot! Our home, with the private guest suite and deck, is situated perfectly for your Vermont holiday.

Overlook at the Office
Fall in love with Bristol. This sweet one-bedroom efficiency right in the Gateway to the Green Mountains has everything you need, whether you are looking for a short weekend getaway or longer seasonal stay. Opening up this listing with all new small-kitchen appliances, queen bed, and new bathroom. Central to the town park and stores, and only miles away from ski areas, hiking trails, and water activities.

Suite in the Green Mountains
We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".
Popular amenities for Middlebury family-friendly rentals
Family-friendly home rentals with a hot tub

Lake Dunmore Getaway — Foliage Views & Ski Retreat

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

Hilltop Haven

Scandinavian design Chalet w/ private hiking trail

Lower Yurt Stay on VT Homestead

Cozy Cabin -Top of Hill with Views

#7 - Hemlock Hideaway Cabin

Brthtkng New Premier Lake Champlain Wfrnt Escape!
Family- and pet-friendly home rentals

Unique Rustic Adirondack Cabin

The Trailhead

Nature Lover's Paradise

The Guest House at Sky Hollow

"Dragonfly Apartment" Private Bristol Apartment

Private Guesthouse in the heart of Vergennes

The Shepherd's Crook at Blue Pepper Farm

Orchard Guesthouse - 1 mile to Middlebury
Family-friendly home rentals with a pool

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

Epic Views of the Green Mountains

Sugarbush Mountainside Retreat - Ski in Ski out

Moon Valley Country Retreat no clean fee pets yes

Spruce Peak Lodge Studio Mnnt Views! | 1516

Spacious Private Apartment w/ Green Mountain Views

Beautiful Spacious Condo at Killington Resort

1 night Ok at the base of Pico 1 bedrom Ski in out
Quick stats about vacation rentals that are family-friendly in Middlebury

Total vacation rentals
Explore 40 vacation rentals in Middlebury

Nightly prices starting at
Middlebury vacation rentals start at $126 CAD per night before taxes and fees

Verified guest reviews
Over 2,540 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Middlebury vacation rentals include wifi access

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

4.9 Average rating
Middlebury stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Okemo Mountain Resort
- Sugarbush Resort
- Gore Mountain
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Fox Run Golf Club
- Montshire Museum of Science
- Leahy Center for Lake Champlain
- Burlington Country Club
- Ethan Allen Homestead Museum
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Adirondack Extreme Adventure Course
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery