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Kid-friendly holiday rentals in Cavendish

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Cavendish

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

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Cabin in Hubbardton

4.74 out of 5 average rating, 70 reviews

Flamingo Cottage

A quiet lake front cottage close to many Vermont attractions. Located next to Lake Hortonia Dam the sound of falling water will provide a relaxing backdrop to your getaway. You can prepare your own meals or dine out at several excellent restaurants. Great place for Kayaking and Leaf Peeping. Now have trash service for renters. Depending on the weather the road leading up to my road requires four wheel drive. When it is plowed it is passable but requires care. It is a dirt road up a hill.

Guest favourite

Home in Hoosick Falls

4.92 out of 5 average rating, 12 reviews

Enjoy Fall & Experience Beautiful Changing Colors

Nestled on a private 5 acres lot on the border of NY and Vermont this home is just perfect. Just 30-60 minutes from several ski areas. This charming home has everything you need to relax and enjoy . The night sky perfect for stargazing. Have morning coffee on the deck and watch as deer wander in the fields or the cows across the meadow. Enjoy a quiet evening by the fire after a long day on the slopes or soak in the oversize soaking tub! Stroller, changing table and a pack-n-play included.

Cottage in Newbury

4.87 out of 5 average rating, 117 reviews

Country Cottage

Charming cottage with 3 bedrooms just a small walk to Sunapee lake. You can enjoy swimming off the dock or explore one of the many harbors on the lake. Mount Sunapee is just around the corner (2 minute drive) and offers many fun activities for the whole family. Including zip lines, mtn biking and much more. Sunapee State beach is also within walking distance or just a short drive away. Offers large sandy beach. This rustic cottage is a perfect place to make memories with family and friends.

Home in Jamaica

4.78 out of 5 average rating, 54 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 favourite

Home in Mount Holly

4.92 out of 5 average rating, 115 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Guest favourite

Home in Rutland

4.8 out of 5 average rating, 337 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

Guest favourite

Home in Windham

4.86 out of 5 average rating, 110 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.

Home in Antrim

4.82 out of 5 average rating, 120 reviews

Quiet House in the Woods

Relax with the whole family at this peaceful place to stay. - Gregg Lake 5 mins away (Swim, Volleyball, Swings, Boat Docks) - Great hiking trails (Monadnock & Miller State Park) - Ski in the winter (Crotched Mountain 20 mins away, Pats Peak 30 mins away) - Small town: Mom & Pop shops/restaurants, Antique stores - 2 Decks: Out door dining & sitting areas This is not an investment property, this is my home. Please be respectful of the property. Thank you! Hope you enjoy your stay!

Guest favourite

Home in Enfield

4.95 out of 5 average rating, 19 reviews

Upper Valley Shaker-Style Home, close to Dartmouth

Located within minutes to Dartmouth Health Medical Center and Dartmouth College, this home offers a comfortable, warm place to gather with friends and family during your visit to the Upper Valley. Just off Route 4, this home offers easy access to I-89 and I-91. This home is unique in its location and proximity to Mascoma Lake. A common right of way and short walk will lead you to the lakefront park and rail trail, where the views are breathtaking. Snowmobile access to rail trail

Guest favourite

Home in Plymouth

5 out of 5 average rating, 13 reviews

Luxury Modern Cabin near Okemo & Killington

All-seasons fun for the whole family in this brand-new home with unparalleled privacy! Modern design elements, tranquil scenery, and 21st century comforts set the backdrop for the perfect getaway. Enjoy ski season in this mountainside abode that's 10 minutes from Okemo, 20 minutes from Killington, and close to downtown Ludlow & Camp Plymouth State Park. Golfer-friendly in spring, summer, and fall. In all seasons, enjoy hiking, leaf peeping, brewery hopping, and swimming.

Guest favourite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favourite

Flat in Pittsford

4.97 out of 5 average rating, 32 reviews

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

Holiday rentals for every style

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Popular amenities for Cavendish family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home in Manchester

4.87 out of 5 average rating, 23 reviews

Charming Vacation Home in Manchester Center

Guest favourite

Home in Salem

4.98 out of 5 average rating, 189 reviews

Magical Farm Getaway - a must visit!

Guest favourite

Home in Brattleboro

4.95 out of 5 average rating, 119 reviews

Spacious Brattleboro home on river, walk to town

Guest favourite

Home in Salisbury

4.95 out of 5 average rating, 101 reviews

Lake Dunmore Home close to skiing & Middlebury

Guest favourite

Home in Bridgewater

4.85 out of 5 average rating, 119 reviews

Blueberry Hill Escape Pet Friendly HotTub Fire pit

Guest favourite

Home in Townshend

4.95 out of 5 average rating, 82 reviews

Cozy, Comfy Country Home in Southern VT Village

Guest favourite

Home in Wilmington

4.87 out of 5 average rating, 101 reviews

MtSnow * Hot Tub * Pool * Air Hockey * PingPong * Darts * 16ppl

Guest favourite

Home in Dover

5 out of 5 average rating, 8 reviews

Walking distance to Lifts. Avoid Parking Fees!

Family-friendly apartment rentals

Guest favourite

Flat in Brattleboro

4.9 out of 5 average rating, 354 reviews

Quiet St in Town, gardens, terrace

Guest favourite

Flat in Ludlow

4.92 out of 5 average rating, 148 reviews

Great Downtown, walk to everything

Flat in West Brattleboro

4.76 out of 5 average rating, 131 reviews

Cute, Convenient with Big Backyard

Flat in Town of Rockingham

4.82 out of 5 average rating, 176 reviews

Apartment on Main Street

Guest favourite

Flat in Ludlow

4.92 out of 5 average rating, 270 reviews

Okemo Vermont Getaway

Guest favourite

Flat in Keene

4.94 out of 5 average rating, 215 reviews

The Carriage House Loft: Seasonal Stays

Guest favourite

Flat in Woodstock

4.87 out of 5 average rating, 124 reviews

New Modern Apartment - Woodstock Village on Mt Peg

Guest favourite

Flat in Keene

4.93 out of 5 average rating, 122 reviews

Apartment in Keene

Family-friendly apartment rentals

Guest favourite

Apartment in Grantham

4.96 out of 5 average rating, 113 reviews

Cozy Light-filled Condo in Charming Eastman

Guest favourite

Apartment in Dover

4.99 out of 5 average rating, 115 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Guest favourite

Apartment in Dover

4.87 out of 5 average rating, 235 reviews

Mt Snow Ski In/Out at Seasons

Guest favourite

Apartment in Killington

5 out of 5 average rating, 32 reviews

Killington Condo-Indoor Pool/HotTub/FitnessCenter

Apartment in Ludlow

4.84 out of 5 average rating, 122 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

Guest favourite

Apartment in Stratton

4.94 out of 5 average rating, 96 reviews

Great 2 bedroom condo at Stratton Mountain

Apartment in Killington

4.8 out of 5 average rating, 105 reviews

Ski Mountain Escape: 3 Bdrm, Ski In & Bus In

Apartment in Killington

4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

Quick stats about holiday rentals that are kid-friendly in Cavendish

Total rentals
20 properties
Nightly prices starting at
₹18,188 before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore