Family-friendly vacation rentals in Middlesex

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.

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.

Zenbarn Loft 1 | 2BR Apt | VIP Perks & Live Music

Zenbarn Loft: A Cozy 2-Bedroom Retreat Above Vermont’s Iconic Music Venue 🎶⛰️🍻 Stay in the heart of Vermont, just minutes from Stowe, Waterbury, and top breweries like Alchemist and Lawson’s! This 2-bedroom suite offers a cozy retreat with a kitchenette, fast WiFi, and a private entrance (shared hallway). Live music below creates a vibrant atmosphere. Please message us before booking with any questions to ensure this is the perfect stay for you!

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.

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.

Lovely Waterbury Home (Crossroads of Recreation)

Nestled in the hills of Vermont, our home is a new 3 bedroom house with a large deck and finished basement. There's also a large yard outside for kids to run around. We're a short one-mile walk to downtown, where there is a quaint small-town feel. And once downtown, you'll find several restaurants and bars where you can sit outside and enjoy the fresh air.

Quiet, Cozy Loft w/ Mountain View’s! Remote Work!

Exceptional value. Charming, comfortable and cozy second story Loft. Open concept living with exposed beams and cathedral ceiling. A true rustic Vermont experience as you relax after a day of skiing, hiking, mountain biking, or simply enjoying the beauty of the Mad River Valley.