Family-friendly holiday rentals in Middlesex

Cozy Farmhouse Nestled Between Stowe and Waterbury

Beautifully restored 1840's era farmhouse is the ideal retreat for ski vacations, hiking, biking & exploring lakes and streams, hanging with friends & family and work from home & homeschooling stays. Features post & beam construction, wide plank flooring, luxurious radiant heat, stainless steel appliances, large windows and powerful WiFi. Clean, cozy, and loads of character combining the best of old and new. Pls msg w/a few trip/group details before instant booking as we are on multiple sites!

Beautiful 30ft Yurt in the Green Mountains!

Gorgeous 5 STAR 30-ft yurt. The wrap-around deck looks out to the Worcester Range, trails leading from the yurt to babbling brooks. This charming space includes a fully equipped kitchen and a private bathroom with a claw foot tub/shower. Two queen beds, air mattress & futon mattress. 12 mi. to Montpelier and 7 mi. in the opposite direction to Lake Elmore, 4 miles to Worcester Trailhead and 6 miles to Hunger Mt! A beautiful sanctuary for peace and quiet or Netflix and Wifi, your hearts desire!

Entire 2nd Floor Walk to Montpelier

Five minute walk to the prettiest and coolest state capital in the country. Entire second floor duplex with separate entrance up a flight of stairs. Beautiful porch. Perfect base to explore Vermont; hiking, skiing, biking. Hosts live downstairs. Dogs are welcome with conditions. (Note the reservation requirements) Limit 4 people. (Includes toddlers and infants) If you are a skier, we're e less than an 40 minutes to major Ski areas. You won't have to pay resort prices and have a more room.

Lovely one-bedroom apartment

The apartment is centrally located - 5 minutes from Ben & Jerry's and Waterbury Village; 20 minutes from Stowe with great biking and hiking and 30 minutes from Burlington and Lake Champlain. Enjoy the spectacular views and relaxing atmosphere on your private deck. Although the apartment does not have air conditioning, it stays a cool 65 degrees on most days - you may even want to turn on the heat early on a summer morning! We require a minimum of a three-night stay.

Tiny House at Camp Comyns

NO check in. Total privacy. Tiny House with a big heart! This magical place is located 3 miles from Waterbury (I-89 exit 10), walking distance to Camel's Hump hiking trails and the Long Trail. Cross Vermont biking, VAST snow mobile trails, kayaking, swimming, fishing, skiing and more. Breathtaking views of mountains, gorgeous foliage. Great restaurants, breweries and live music all within five miles. Plenty of parking. Close to Stowe, Montpelier, and Burlington.

Private 4-Season Country Yurt Close to Town

Nestled in the woods on a quiet country road, this cozy retreat is a perfect getaway just ten minutes from downtown Montpelier. Enjoy nearby historic sites, boutique shops, and delicious restaurants. Cozy up during the colder months by the pellet stove with a book, sit on the porch with a cup of coffee and enjoy a summer morning, or get out and explore the nearby trails, ponds, and dirt roads. Solo travelers, couples, and families enjoy this unique, clean, space.

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room is very cozy with radiant heat in the floor during the winter. The separate entrance is off a covered porch. The porch has chairs and a table and is very pleasant in the warmer months The little kitchen alcove is convenient for coffee or tea or a light meal. We live in a historic building and our neighborhood is located very close to Rte 100. Waterbury village and Stowe as well as skiing, hiking and biking are all nearby.

44 Degrees North

This cozy 3 bed 2 bath cabin is situated on the southern end of the Worcester Range in Waterbury Center. Enjoy beautiful sunsets over Camel's Hump and Bolton Mnt while sipping cocktails on the deck. Or warm up in the in the hot tub during the winter while watching the cats groom the trails at Stowe . Hike, bike and snowmobile from your doorstep or treat yourself to VT craft beers and eats just a short 5-7min drive away.

House in beautiful rural Plainfield

Our house in rural Plainfield is a quiet place to enjoy Vermont's country roads, fields, mountains and night skies. Summer in Vermont is glorious, with blue skies, verdant fields, and full gardens. In fall, the maples turn red, orange, and gold. We welcome people of all races/nationalities. We strive to accommodate people with disabilities. We love to host families with babies and young children.