Family-friendly vacation rentals in Middlesex

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Top-rated family-friendly rentals in Middlesex

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in East Montpelier

4.94 out of 5 average rating, 269 reviews

Cottage Farmhouse Apartment in Heart of Vermont!

A sweet, bright, spacious, private second floor cottage-apartment in our 1830's brick farmhouse, close to Montpelier the bustling state capital, completely redecorated for guests with a comfortable queen bed in the sleeping area, vintage farmhouse kitchen and lovely living/dining room. Refinished maple floors and travertine tiled bathroom with a rain shower. Nestled into the countryside with eastern mountain views & active farm fields -glorious morning sun and black-out shades for sleeping in.

Apr 21 – 28

ﺩ.ﺇ447 per night

Guest favorite

Bungalow in Worcester

4.97 out of 5 average rating, 586 reviews

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!

Sep 8 – 15

ﺩ.ﺇ628 per night

Guest favorite

Apartment in Montpelier

4.87 out of 5 average rating, 604 reviews

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.

Jan 26 – Feb 2

ﺩ.ﺇ471 per night

Guest favorite

Home in Waterbury Center

4.96 out of 5 average rating, 117 reviews

Peaceful setting with Mountain Views

Rent the entire house. Large primary w/ private bath, 2 bdrms comfortably accommodate 4 people w/ a shared full bath, one bonus room with pull out couch. Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (available from Memorial Day till Thanksgiving), outdoor fire pit, all on 8 acres. Located centrally to three ski resorts, mountain biking, hiking , kayaking, swimming, you name it. An inviting home in any season!

Nov 15 – 22

ﺩ.ﺇ1,937 per night

Guest favorite

Yurt in Montpelier

4.95 out of 5 average rating, 509 reviews

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 to downtown Montpelier and I-89. Nearby historic sites, boutique shops, and delicious restaurants make your time in Vermont memorable. Hundreds of miles of trails for cycling and skiing nearby. Guests love settling in with the unique books and board games. Enjoy a campfire and the covered deck in the warmer months and a wodstove's comfort fall, winter and spring.

Apr 6 – 13

ﺩ.ﺇ405 per night

Guest favorite

Guest suite in Waterbury Center

4.94 out of 5 average rating, 415 reviews

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.

Mar 19 – 26

ﺩ.ﺇ203 per night

Guest favorite

Apartment in Waterbury Center

4.89 out of 5 average rating, 174 reviews

Basecamp Waterbury - center of it all!

PLEASE READ FULL DESCRIPTION BEFORE BOOKING - and I prefer a message over instant book just to make sure you don't have any questions and I don't have any conflicts. You can't get more centrally located to everything Vermont has to offer. 5 minutes to downtown Waterbury, 10 minutes to Stowe, Half an hour to Burlington or Mad River. There is a shared hallway entry with the downstairs apartment but only the one exterior door in common.

Jun 8 – 15

ﺩ.ﺇ456 per night

Guest favorite

Cabin in Waterbury Center

4.97 out of 5 average rating, 174 reviews

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.

May 8 – 15

ﺩ.ﺇ1,082 per night

Guest favorite

Guesthouse in Groton

4.98 out of 5 average rating, 246 reviews

Groton Forest Retreat

Comfortable, secluded, sparkling clean 2nd story loft IN Groton State Forest, and offering privacy, peace, and quiet. Forest trails outside your door; star-gaze with little to no light pollution! Hike, byo bike, swim, byo kayak, explore; foliage in Fall. To ensure the safety of all guests, A&K are fully COVID-19 vaccinated and ask all guests to be fully vaccinated as well.

Nov 22 – 29

ﺩ.ﺇ437 per night

Guest favorite

Cottage in Waitsfield

4.94 out of 5 average rating, 223 reviews

The Bent Hill Schoolhouse

The Tinmouth Vermont Schoolhouse c.1840, was moved and restored in 1981 to Bent Hill Settlement in Waitsfield Vermont. This charming, private one-room schoolhouse sits on 6 acres and has been newly updated in 2017. A fully equipped kitchen is at your disposal. Private bath off open living space. Bedroom upstairs in the garret. Outside patio table and gas BBQ grill.

Oct 25 – Nov 1

ﺩ.ﺇ417 per night

Guest favorite

Home in Moretown

4.98 out of 5 average rating, 132 reviews

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.

Mar 21 – 28

ﺩ.ﺇ667 per night

Guest favorite

Apartment in Waterbury

4.93 out of 5 average rating, 347 reviews

Beautiful Victorian

Ski, hike, hit the local pubs and breweries. Walking distance to some of the best beers in the US! Easy drive to 5 ski areas, great, safe neighborhood, Coffee machine, fridge, oven, and microwave. Cozy atmosphere. Suitable for young kids but not ideal as there are people that live upstairs and the place has breakable decorations.

Apr 24 – May 1

ﺩ.ﺇ774 per night