Kid-friendly vacation rentals in Windham County

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Top-rated kid-friendly rentals in Windham County

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

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Top guest favorite

A spacious two-story home is nestled among lush greenery, featuring a light pink exterior complemented by maroon shutters. A paved driveway leads to a double garage, while a well-maintained lawn and garden enhance the inviting atmosphere of the property.

Home in Whitingham

5 out of 5 average rating, 57 reviews

2.5mi from the lake! Fire pit, arcade, yard games!

Escape to our tranquil countryside retreat, where relaxation meets adventure. Nestled amidst nature, our cozy home offers a haven of tranquility. Breathe in crisp air as you unwind in the peace & quiet. Indulge in outdoor pursuits with skiing, hiking, and foliage just moments away. After a day of exploration, find solace in the inviting warmth of our home. Whether you're curling up with a book or stargazing by the fire pit, every moment becomes a cherished memory. Your idyllic VT retreat awaits.

Top guest favorite

A cozy chalet is set on a lush green landscape, surrounded by towering trees. The two-level structure features a prominent balcony and a welcoming entrance, with a gentle slope leading toward the house. A grill is positioned on the lawn, ready for outdoor cooking.

Chalet in Stratton

4.99 out of 5 average rating, 167 reviews

Chalet w/Disc Golf & AC near hike/bike/golf/swim

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled June 2023! Open floor plan w/wood burning fireplace. Main bedroom has Qn bed & twin bunks. Finished basement with new Qn size bed and twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property!

Superhost

The exterior of a contemporary A-frame house is set amidst a forest, featuring a new deck with outdoor space. A pathway made of stones leads to the entrance, while sunlight filters through the surrounding trees, casting soft light on the facade.

Home in Jamaica

4.75 out of 5 average rating, 57 reviews

Green Mountain A-Frame with HOT TUB near Stratton

Our cozy Green Mountain A-Frame is the perfect place for your Vermont getaway! A perfect combination of modern meets eclectic charm. Newly added deck with 7 person hot tub for your enjoyment. Nestled on a private road in town, you can’t go wrong! Hike from the house or head down the road to Jamaica State Park. High-demand ski resorts are just minutes away - only 6 minutes to the Stratton Mountain access road, 17 minutes to Magic Mountain, 20 minutes to Bromley and 30 minutes to Mt. Snow.

Guest favorite

A charming cottage is nestled in a snowy landscape, surrounded by evergreen trees. The red exterior contrasts with the white snow. A stone chimney rises from the roof, and a small garden area is visible in the foreground, adding interest to the serene winter scene.

Cottage in Chester

4.91 out of 5 average rating, 162 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guest favorite

A game room features a light wooden floor beneath a sloped wooden ceiling. An air hockey table is situated in the foreground, alongside a wall display of Nerf guns. A staircase and large glass door provide access to the outdoors, enhancing the room's spacious feel.

Home in Wilmington

4.96 out of 5 average rating, 114 reviews

Family Downtwn Retreat Wilmington-HotTub Firepit

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

Top guest favorite

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Apartment in Wilmington

4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Superhost

A vintage-style kitchen features a classic stove with a kettle on top. A wooden dining table with chairs is positioned by a large window, allowing natural light to fill the space, while greenery is visible outside.

Home in Windham

4.87 out of 5 average rating, 113 reviews

Magic Creek

Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

Top guest favorite

The kid zone features a spacious area with two oversized bean bags covered in a soft, spotted fabric. An air hockey table is positioned to the left, while a chalkboard scoreboard hangs on the wall, providing a playful touch for games.

Home in Wilmington

5 out of 5 average rating, 14 reviews

Spring Hiking Pet Retreat I Game RM l ChimneyHill

This spacious Pet friendly 3-bedroom + home near Mt Snow offers a full kitchen, deck with grill, kids space with air-hockey, chip n'put as well as Chimney Hill Clubhouse Amenities: Indoor/outdoor Pool, hot tub, tennis courts +more. A short walk takes you to trail access for Haystack Mtn. Perfect for a mountain retreat with family or friends! Bedrooms: 1st floor- 1 bedroom with Queen bed 2nd floor - 1 King Bedroom , 1 Queen Bedroom - 1/2 bath Kidzone - open living area 2 twin beds

Top guest favorite

Cabin in Whitingham

4.99 out of 5 average rating, 105 reviews

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

Top guest favorite

The spacious A-frame home is set against a backdrop of vibrant trees and lush greenery. A well-manicured hill leads to the house, which features large windows allowing natural light to fill the interior. The bright blue sky complements the tranquil outdoor scenery.

Chalet in Dover

4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Charming spacious A-frame with lots of natural light, beautiful scenery and wrap around deck. Property features a long rolling hill perfect for sleigh riding or 75' slip n slide, tennis court, firepit, and 5 acres of Green Mountain Nat'l forest and brook. Home has 3 bedrooms + loft area.. 5 miles to Mount Snow, and minutes to golf course, bars/restaurants and lakes. This house is action packed inside and out with hot tub, 200' zipline and "unlock the box" scavenger hunt.

Guest favorite

The exterior of a spacious home is presented, featuring a light-colored facade and a welcoming red door. The surrounding area is partially covered in snow, with pine trees in the background and a fire pit area visible on the lawn.

Home in Wilmington

5 out of 5 average rating, 26 reviews

Kiki's Mountain Chateau

Refresh and reset within this spacious, serene space destined to be a memorable family retreat. A charming getaway with all the comforts of home with the best nature has to offer. Located in the small town of Wilmington and just a short scenic drive to Mount Snow. Local watersports, winter sports, nature trails, foliage, bird watching, stargazing and plenty of local charm. Kiki's has enough room for everyone to unwind or gather together. ***Hot Tub has arrived!

Guest favorite

A game room is illuminated by large windows, providing views of the greenery outside. A foosball table sits prominently, alongside a multi-sport game featuring a basketball hoop and a net for volleyball. The space encourages active play with a modern and inviting setup.

Condo in Dover

4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.