Family-friendly vacation rentals in Cavendish

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Cavendish family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite

Home in Plymouth

4.95 out of 5 average rating, 243 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

OliviaRating, 5 stars4 days ago
Really great stay! The house was clean and fit our group of 6 perfectly. Location was super close to Killington for skiing. Just an fyi if here in the winter - there’s a large hill to get to the house that is covered in snow/ice. Make sure you have a car with all wheel drive or a snow mode to get up as one of our cars wasn’t able to get up the hill!
Guest favorite

Chalet in Killington

4.83 out of 5 average rating, 242 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

JoeyRating, 5 stars2 weeks ago
Great place to stay! Fantastic house, great location, crystal clear communication, thorough house instructions, countless house amenities. Looking forward to book again! 10/10 experience.
Guest favorite

Condo in Dover

4.87 out of 5 average rating, 234 reviews

Mt Snow Ski In/Out at Seasons

TaraRating, 5 stars3 weeks ago
Great experience renting from Andrew. Very responsive, within minutes any time we reached out. Place was super convenient to get to the slopes. Locker outside the front door was convenient as well to keep our snowboards and skiis. Our family had a great time in Mt. Snow and hope to be back.
Guest favorite

Chalet in Ludlow

4.95 out of 5 average rating, 120 reviews

Okemo Ski Chalet with Hot Tub

JosueRating, 5 stars2 months ago
Bob was an amazing host. The whole time he was very responsive and helpful with anything we needed! He made sure we felt comfortable and at home. The house was absolutely gorgeous!
Guest favorite

Chalet in Stockbridge

4.92 out of 5 average rating, 177 reviews

Killington ski house winter MTbike -new jacuzzi

MichelleRating, 5 stars1 month ago
Dean was very proactive with communicating about our stay and giving helpful tips on getting to his place. It was in a great location. His place was clean and spacious, with everything we needed. We had a great stay! Thanks Dean!
Guest favorite

Chalet in Killington

4.87 out of 5 average rating, 244 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

JakeRating, 5 stars4 days ago
Cammie was a great host. She was very responsive and helpful
Guest favorite

Condo in Killington

4.96 out of 5 average rating, 133 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

SidneyRating, 5 stars3 days ago
Alex's condo in Killington (Trail Creek Condo #45) was a pleasure to stay at over the MLK weekend! My family of 4 adults and 3 children found the space very comfortable and spacious with all of the amenities that one would want for a long ski weekend. We cooked all of our breakfasts at the condo which was easier to do with all of the supplies that Alex provided. The beds were super comfy to sleep on and we heard no noise from outside or from our neighbors. The in-unit sauna was a joy to use after a long day on the mountain. There is a very convenient easy/green ski-in trail that made the end of our ski day much easier. All in all, Alex provided a wonderful experience and we'd happily recommend his condo to anyone looking for a superb stay in Killington.
Superhost

Apartment in West Townshend

4.9 out of 5 average rating, 335 reviews

Private Apt on Farm, Hot Tub with views!

Eva & PeterRating, 5 stars2 weeks ago
We had a beautiful time as Roberts home is so peaceful with the incredible winter views! It was a frigid weekend so unfortunately we couldn’t really enjoy the hot tub even though we did venture in it for a quick 15 minutes . Do not recommend doing this in negative wind chill! The apartment had everything we needed for a cozy stay. Robert met us at the parking area and gave us a great recommendation for dinner - the Grafton Inn Barn Pub restaurant was so quaint in a an old barn with a fire going in their two story fireplace. What a treat also to learn what an incredible glass blowing artist Robert is. We visited his gallery workshop and watched him and his assistants create glass bowls and purchased a colorful glass pumpkin and an ornament. We loo forward to our next visit when we can see the farm and animals in full bloom!

Family- and pet-friendly home rentals

Guest favorite

Cabin in Jamaica

4.88 out of 5 average rating, 108 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

HeleneRating, 5 stars3 weeks ago
Great host ! Great home . Close to the ski resorts . I would definitely give her place beyond five stars. So easy to communicate with Christina.. I would definitely stay at her home again. Thank you for a great experience ! Helene
Guest favorite

Home in Goshen

4.83 out of 5 average rating, 282 reviews

Nature Lover's Paradise

TeresaRating, 5 stars1 month ago
Gorgeous house in a great location, close to lots of hiking trails. It was nice to return to relax in the comfy living room then prepare supper in the well-equipped kitchen. The grounds are beautiful, and the dog enjoyed sniffing around. Philip is the perfect host. Hoping to return soon!
Guest favorite

Cabin in Danby

4.89 out of 5 average rating, 292 reviews

Great Location excellent Cabin

JenniferRating, 5 stars2 weeks ago
A very nice Airbnb for a night or two for a couple. Although, it had more beds to accommodate more than two, the main living area is quite small. Especially, since we had large ski bags with us and no where to really put them. The larger queen bed is up a ladder. I wasn’t going to haul bags up there and The downstairs bedroom has enough room for the full bed and two tiny end tables. It is the smaller of the two spaces, and our luggage would not fit there, so it sat in the tiny living area. Outside of that, the place was very clean, there were nice snacks left for us which I really appreciated and the host was so lovely. She even made us blueberry muffins. The location is about 15 minutes to Manchester and 35 min to Okemo.
Guest favorite

Tiny home in Jamaica

4.94 out of 5 average rating, 1,230 reviews

Apple Blossom Cottage: A Tiny House

JennyRating, 5 stars1 week ago
We had a wonderful stay. The space was exactly as described and about 15 minutes from the Stratton access road. Our pup loved the yard and even played with Domenics pup Ringo. Would definitely stay again.
Guest favorite

Home in Rochester

4.95 out of 5 average rating, 190 reviews

The McKinley House

RichardRating, 5 stars1 week ago
Dan and Peggy's place was great for a trip to Killington! House is very cozy, plenty of space to relax and chill. Hosts were communicative and logistics were very smooth.
Guest favorite

Guest suite in Mt Holly

4.98 out of 5 average rating, 129 reviews

Exquisite Green Mountain Loft Haven

SaraRating, 5 stars2 months ago
Brigid’s beautiful loft apartment was the perfect place to stay during our recent family gathering in Belmont. It’s spotless, well equipped, and located not far from the center of town and Star Lake. We’d love to stay there again next time we’re in Belmont.
Guest favorite

Chalet in Wells

4.89 out of 5 average rating, 141 reviews

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

BrendonRating, 5 stars4 days ago
Beautiful place with a wonderful host! The views from the deck and the fireplace were our highlights. Would highly recommend staying here!
Guest favorite

Guest suite in Norwich

4.97 out of 5 average rating, 112 reviews

"Downtown" Norwich Apartment

LaurenRating, 5 stars3 months ago
We loved our stay in Norwich. The apartment was cozy and very clean. The views into the meadow were beautiful and the trails connecting in the back were a fun hike as well. We were close to many attractions. Lily was a great communicator and was very kind to allow me to call her directly to problem solve an issue during our stay, it was much appreciated!

Family-friendly home rentals with a pool

Guest favorite

Townhouse in Dover

4.96 out of 5 average rating, 145 reviews

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

JulieRating, 5 stars1 week ago
Great place to stay for skiing. Very close to Mt. Snow. Matt was very quick to respond to any questions. The place was well equipped. The fireplace was great and added so much coziness.
Guest favorite

Guest suite in Killington

4.95 out of 5 average rating, 140 reviews

Cozy, private, spacious, 3 bedrooms, 5 mi to K Rd.

ShaynaRating, 5 stars2 weeks ago
We came here for two nights this past weekend and enjoyed the uniqueness and character of the space. This ground-level / basement apartment was super warm on a very cold weekend. We loved the unique art and travel treasures that dot the space. The drive to Killington was easy and quick.
Superhost

Condo in Killington

4.79 out of 5 average rating, 102 reviews

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

KristinRating, 5 stars4 days ago
Our stay was great. The location was perfect for skiing and restaurants. Dray was responsive with our questions before our stay.
Guest favorite

Condo in Killington

4.82 out of 5 average rating, 255 reviews

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

JacquelynRating, 5 stars1 week ago
Perfect accommodation for our party of 5 adults (husband & I, adult children and a girlfriend). We would definitely stay here again. The condo is spacious and we never felt crowded. The kitchen is well stocked. An added bonus is the refrigerator has an ice maker and cold water, something you don't normally see at a rental. Beds were very comfortable and the linens were so soft. There were plush towels. We really loved the location...ski on ski off for Pico. The ski on is a narrow trail and was challenging for the recently categorized intermediate skier of our group. She opted for taking the shuttle back while the rest of us stayed out. We were slightly concerned about the ski off as B Slope was closed for race training. Thankfully by the time we were ready to end our day it was open. The ski off is really for a solid intermediate skiers. The hosts were great to communicate with and accommodated our request for an early check in.
Superhost

Condo in Killington

4.78 out of 5 average rating, 292 reviews

Serene Top Floor Condo (resort style amenities)

MaryRating, 5 stars1 week ago
Great place to stay for a weekend of skiing. Scott is incredibly hospitable, giving us recommendations and checking in on how things were going. The location is fantastic. It’s an easy walk (5-8min) to snowshed lodge or there is a bus right outside. Would definitely stay here again!
Superhost

Condo in Killington

4.88 out of 5 average rating, 155 reviews

Modern Killington Farmhouse Condo: Close to Resort

AdinaRating, 5 stars3 months ago
Our trip was amazing. We’ve stayed in Killington before but it didn’t compare to this experience. The home is beautiful, everything you can possibly need and more !! The host had a few tickets for the gondola that he was able to offer us which saved us a ton of $$ and was more spectacular than our trip to Stowe. All in all, it was 10/10. Thank you for hosting us.
Guest favorite

Condo in Killington

4.93 out of 5 average rating, 429 reviews

Ski in n out Pico 1 bedroom 1 nite Ok free shuttle

BurcinRating, 5 stars4 days ago
This is our second season staying at Gabe’s place. We keep coming back. The location is great especially for Pico and the apt and building is clean and cozy. There is an elevator and locker downstairs which makes your life easier. Highly recommended!
Guest favorite

Condo in Killington

4.97 out of 5 average rating, 141 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

DianeRating, 5 stars3 weeks ago
We stayed here for NYE for a few nights. The condo is exactly how it’s described, we loved that it was so close to the mountain and restaurants. We took advantage of the pool and sauna. It was exactly what we needed to end the year! We would stay here again! Rachel was very easy to deal with and her communication was great. Thank you!

Quick stats about vacation rentals that are family-friendly in Cavendish

  • Total rentals

    90 properties

  • Nightly prices starting at

    $120 before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

Destinations to explore