Family-friendly holiday rentals in Cavendish

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cavendish

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

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Guest favourite

Flat in Springfield

4.91 out of 5 average rating, 222 reviews

Farm Barn apt. 3 bedr, 2 bath, fiberoptic internet

Getaway for families, couples or groups. Apt. in our Barn. High speed internet, so ideal for "work from home". Full kitchen with oven, microwave, dishwasher, big fridge , 3 bedrooms, 2 baths, Dining/Living room with TV ( Antenna, no cable, Roku: bring your passwords for Netflix..) Fields, forest, hill and river on our property. We allow one friendly dog at a time but it is not allowed to stay in the apt. by itself (daycare in Spgf avbl). Please add the dog to your booking for the one time 35 $.

29 May – 5 Jun

€ 109 per night

Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

5–12 Nov

€ 112 per night

Guest favourite

Cottage in Hartland

4.97 out of 5 average rating, 420 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

5–12 Apr

€ 138 per night

Guest favourite

Guest house in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

22–29 Nov

€ 98 per night

Guest favourite

Guest suite in Chester

4.91 out of 5 average rating, 156 reviews

Chester Carriage House-Cozy-Quintessential Vermont

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

13–20 Jun

€ 174 per night

Guest favourite

Flat in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

15–22 Feb

€ 135 per night

Guest favourite

Cottage in Ludlow

4.92 out of 5 average rating, 120 reviews

Ludlow Village Guest Cottage with Prime Location

Renovated one bedroom, one bath guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entrance to Okemo Base Lodge. Anything you need can be found a short walk from the front door including a wide variety of restaurants, shops and bars for Après Ski. Sitting on the weekend and holiday shuttle route to Okemo, its the perfect spot to be! Cottage has a fully equipped kitchen and wifi for your technology needs.

7–14 Oct

€ 125 per night

Guest favourite

Guest house in Hartland

4.95 out of 5 average rating, 913 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require atleast a two night stay for the whole month of October. There is a "one" night stay fee of $40 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas grill available May - October

26 Mar – 2 Apr

€ 151 per night

Guest favourite

Guest suite in Mt Holly

4.98 out of 5 average rating, 117 reviews

Exquisite Green Mountain Loft Haven

Lovely apartment in country home affords privacy plus all the necessities of home. Beautiful grounds and views afford relaxation and invigoration. Ski at local ski resorts or snowshoe or sled right outside your door. Comfortable beds, peace and quiet, and dark skies means great sleeping. Fully stocked kitchen, and nearby summer activities makes staying here fun and enjoyable. Come find out what others already know!!

23–30 Nov

€ 147 per night

Guest favourite

Flat in Rutland

4.96 out of 5 average rating, 523 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

2–9 Apr

€ 102 per night

Guest favourite

Home in Ludlow

4.97 out of 5 average rating, 147 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Much of the house newly renovated in the Fall, 2023. Relax in this 3-level (1700+ sq. ft) ski chalet that's a 4 min drive to the Okemo Mountain Resort and the center of town, and a 6 min drive to Jackson Gore. Take in the 180-degree views of your wooded backyard with floor-to-ceiling windows and unwind in front of the fireplace or relax in the Jacuzzi hot tub in your private oasis on the mountain.

4–11 Jun

€ 372 per night

Guest favourite

Flat in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

30 Sep – 7 Oct

€ 120 per night