
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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Cavendish family-friendly rentals
Kid-friendly house rentals

The Little Blue House
Stayed with a few friends for our ski trip to Okemo and it was perfect! Marti's place is a short drive from the resort and close to Singleton's for general store needs. The home was clean, beds were comfortable, kitchen was well stocked with pots & pans, mugs, cups, etc. Parking was easy in the driveway, check-in was easy with the keypad, temperature control was easy with the Nest thermostats, the TVs with chromecast were perfect for watching movies, everything was great. Sadly, we didn't get time to use the hot tub, but we'll have to come back! Marti was a great host, responding promptly to our questions and had a guest manual with all the info we needed.

Charming New England Cape
Really nice peaceful place to stay. Was super clean and a most interesting house with many antiques, brought back many memories from childhood. Host was very responsive and very friendly. Would definitely stay there again!

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views
Awesome place! All the games in the basement gave us something to do while hanging inside the house. It’s great being able to come back after a long day of snowboarding and relaxing in the hot tub. The kitchen had everything we needed to cook. Only thing “negative” I could say is we couldn’t find any trash bags for the trash cans but obviously not that big of a deal. Overall I would 100% recommend and would definitely stay here again, without a doubt

The Bluebird Day Chalet 2 bed dtwn Ludlow Village
It is a great place. Convenient to downtown and a short ride to Okemo.

Vermont Botanical Studio Apartment
I’ve returned to the Vermont Botanical studio on an annual basis for several years, since I always find it peaceful and comfortable—off the beaten path, but not lonely. It has everything I need, including a dirt road through the fields for a daily walk, tall windows looking out on lovely trees, a very healthy songbird population, and a nearby farm store where I always go to buy cheese as soon as I arrive. I especially appreciate the comfortable bed, reading chair and couch, and the perfectly serviceable kitchen. The induction range makes for very quick cooking, and it’s nice to have the use of a full-sized fridge, too. For my writing retreats, the studio feels like a home away from home.

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

Cottage on Main Okemo Mountain new decor AC, WIFI
Jennifer’s place was perfect for a ski weekend for our family. We felt right at home and it had everything we needed. The place was very clean and had comfy beds. Easy drive to Okemo and surrounding restaurants. Jennifer was very helpful and responsive when needed. Would stay again for sure!

The Grafton Chateau
The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.
Family-friendly apartment rentals

Gorgeous 1-Bedroom Space in Historic Bellows Falls
Remy was a great host! Perfect place to stay in Bellows Falls! Easy parking and great restaurant right below! Highly recommend staying here!

Beautiful 2 Bedrooms in Mountains w/ full kitchen
Nancy is a responsive host who provides clear instructions and offers local recommendations. The apartment we stayed in worked perfectly for our ski weekend at mount snow with 2 teens. Plenty of room and amenities within to foster a fun and relaxed family weekend. The maple syrup for purchase was a delicious touch. Would definitely stay again if we returned to the area.

Sunny Studio Apartment in Hartland
Nancy's place was a great place to stay, very private and quiet with beautiful surroundings. Easy access to Quechee and Woodstock (~20 min). Skunk Hallow Pub and Farmer's Market just down the street and Harpoon, Simon Pearce factory in Windsor easy to get to. Hope to visit again soon. Nancy's is a fantastic host!

Dog heavenly! Private, beautiful and relaxing.
Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

Apartment on Main Street
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

LOG HOME APARTMENT IN WOODST. VILLAGE 3 night min.
We absolutely loved our stay with Bob and Sherry. They were so kind and attentive on the app, providing recommendations and checking in frequently when the weather turned on us. Although we were technically in their home, it still felt very private. The apartment is beautifully done and I’m obsessed with the pine wood everywhere. We would absolutely return and cannot recommend this little place highly enough!

Hearth House Farm
Jean and Wade were wonderful hosts. We especially appreciated the farm fresh eggs and other supplies available upon our arrival. Beautiful rustic countryside location and farm steeped in history as old as the majestic oak trees surrounding it.

Cozy Poultney Village Apartment
We had an exceptional stay at this Airbnb! It was perfect for two people with plenty of room. It was so cozy. We loved the Vermont specific decor. The ingredients for pancakes and the basic ingredients in the fridge were a thoughtful touch. I could not recommend staying here more!!!
Family-friendly apartment rentals

Main St Escape | Explore Downtown Ludlow
Clean, great location, easy check in/out, and friendly host - would definitely stay again.

Dog-Friendly Mtn Escape/AC/Pool/
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Bright Ski on/off Condo Full Kitchen-Free Shuttle!
Couldn’t have asked for more. Cozy, clean and such a comfortable place to stay and exactly what was described in the listing. I’ll certainly be booking again! Tricia’s communication was perfect, everything very clear and didn’t have to reach out with extra questions.

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Cozy Condo next to Resort * AC and Pool *
Claudia was super responsive and the place was amazing!! Within 5 minutes of a lot of great restaurants and very close to great hiking trails. Would love to come back again!

Lovely 1-Bedroom condo with indoor fireplace!
Such an amazing place. Great location for walking to restaurant. Breath taking views especially the river. Extremely homey feel. We will definitely be back. thank you for your hospitality.

Hike bike golf 1 bedroom 1 nght Ok shuttle
Great place great stay as always !!

Killington-Pico ski in/out Studio at base of Pico
Tom was great. Got back to me in a very timely manner. Very pleased with the whole experience. I don’t do this as often as I would like so having a host be very reachable and responsive is a great thing. And the location was to die for. Walking distance to all the festivities. Really can’t wait for next year. I would love to get this location again. Thank you to Tom for allowing us the chance to share his place. Would definitely recommend Tom to anyone 😎🏹
Quick stats about holiday rentals that are kid-friendly in Cavendish
Total rentals
20 properties
Nightly prices starting at
$179 SGD before taxes and fees
Total number of reviews
1.1K 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
- Boston Holiday rentals
- Hudson Valley Holiday rentals
- Montreal Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Family-friendly rentals Cavendish
- Rentals with a hot tub Cavendish
- Rentals with a fireplace Cavendish
- Cottage rentals Cavendish
- House rentals Cavendish
- Rentals with pools Cavendish
- Fitness-friendly rentals Cavendish
- Rentals with a washing machine and dryer Cavendish
- Pet-friendly rentals Cavendish
- Apartment rentals Cavendish
- Rentals with outdoor seating Cavendish
- Rentals with a patio Cavendish
- Rentals with a firepit Cavendish
- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth Skiway
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Ragged Mountain Resort
- Autumn Mountain Winery
- Fort Ticonderoga
- Dorset Field Club
- Tenney Mountain Resort
- Hildene, The Lincoln Family Home
- Northeast Slopes Ski Tow
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Hooper Golf Course
- Brattleboro Ski Hill
- Bretwood Golf Course
- Fox Run Golf Club
- Ekwanok Country Club