Kid-friendly holiday rentals in Roxbury

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Roxbury

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

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Guest favourite

Farm stay in Roxbury

4.96 out of 5 average rating, 166 reviews

Moonlight Mountain Farm Vermont Studio w Hot Tub

Welcome, this is a farmhouse. Our idyllic Farmstay offers a private, spacious, modern studio within a beautiful 1840's farmhouse in rural Roxbury, Vermont. We’re on the dividing line of the Mad River Valley and Dog River Valley’s. Roam our ambling 20 acre property offering a swimming pond, woodland paths and open pastures. Explore the headwaters of the Dog River and power down in the spa room with hot tub. Revel in Vermont's finest skiing, hiking, biking, and beer/food just up and down the road.

15–22 Sep

$326 SGD per night

Guest favourite

Guest suite in Middlesex

5.0 out of 5 average rating, 275 reviews

Morningstar Meadow - your home in Vermont

You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Centrally located 3 miles from Montpelier. Snow tires or all-wheel drive recommended Nov-March.

3–10 Apr

$169 SGD per night

Guest favourite

Cabin in Roxbury

4.97 out of 5 average rating, 188 reviews

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

6–13 Sep

$195 SGD per night

Guest favourite

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

8–15 Apr

$173 SGD per night

Guest favourite

Cabin in Roxbury

4.98 out of 5 average rating, 120 reviews

Cozy cabin retreat

Find peace, quiet, privacy, and fast high-speed internet at this cabin in Vermont's central hills. The cozy, wood cabin overlooks a small stream and beautiful, rolling meadows. Explore the 26 acres on private forest trails, meadow paths, and surrounding dirt roads. We are close to Montpelier, Northfield, Norwich University, the Mad River Valley, and Randolph. Come for foliage, skiing, mountain biking, or relaxing. (45 minutes to Sugarbush base lodge, 1 hour to Stowe and Killington.)

5–12 Apr

$194 SGD per night

Guest favourite

Flat in Roxbury

4.99 out of 5 average rating, 131 reviews

Private Resort Luxury in the Heart of Vermont

Bright and spacious apartment that sleeps 4 in the heart of the central Vermont mountains. Property is 80 Acres surrounded by thousands of acres of state forest. Fully furnished with all amenities with heated indoor parking, air conditioning, and access to amazing outdoor opportunities like skiing and biking in all seasons. The property has high speed Starlink internet. Come enjoy all the seasons Vermont has to offer in complete comfort and ease. Reduced rates for extended stays.

17–24 Jan

$322 SGD per night

Guest favourite

Flat in Waitsfield

4.95 out of 5 average rating, 167 reviews

Historic District Overlooking the Mad River Studio

This beautiful apartment is located the second floor of Bridge Street's most popular building, neighboring the Covered Bridge with views of the Mad River. The setting is gorgeous, the apartment is immaculate and charming. 15 minutes from Sugarbush and Mad River Glen Ski Resorts, endless hiking trails, Mt. biking, kayaking, golfing, swimming, fishing and walking distance to Lawson's Finest Liquids Brewing Company. Please check out our reviews as they have been nothing but positive!

13–20 May

$127 SGD per night

Guest favourite

Home in Roxbury

4.9 out of 5 average rating, 157 reviews

Captain Tom's Cabin - Secluded Vermont Getaway

Welcome to Capt. Tom's Cabin. Nestled in the hills of Vermont with a beautiful view of the Green Mts., this 2-storey, 2 bedroom log house on 44 acres offers seclusion, serenity and privacy. Two large bathrooms, full kitchen, central heat, gas fireplace, pond and deck. Great for winter sports enthusiasts and nature lovers. Good wifi, dog-friendly with a fee. Please google and read Vermont's covid restrictions and agree to adhere to them before making a reservation.

15–22 Oct

$210 SGD per night

Guest favourite

Yurt in Randolph

4.96 out of 5 average rating, 386 reviews

4 Season Lower Yurt Stay on VT Homestead

We are located in the hills of central VT, close to good hiking, skiing and swimming. Our homestead is based in permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. No cleaning fee! This is one of three listings at our place. We can accommodate groups of six by booking: 4 season Lower Yurt Stay on VT Small Farm and Tiny house on VT homestead.

11–18 Nov

$95 SGD per night

Guest favourite

Tiny home in Warren

4.99 out of 5 average rating, 152 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet.

13–20 Oct

$1,101 SGD per night

Guest favourite

Guest house in Warren

4.92 out of 5 average rating, 195 reviews

Beautiful newly constructed 1 Bedroom retreat

Newly constructed 1 Bedroom apartment above our garage for rent in the heart of East Warren. Ski on/off Blueberry Lake Cross Country Center access. We are just 5 miles from Sugarbush Resort and 10 miles from Mad River Glen. Apartment has private outdoor parking and entry. This is directly adjacent our home. We are a family of 6 with 4 high school school aged children and chickens.

5–12 Jun

$204 SGD per night

Guest favourite

Flat in Hancock

4.95 out of 5 average rating, 146 reviews

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 bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

6–13 May

$130 SGD per night