Family-friendly holiday rentals in Killington Ski Area

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Popular amenities for Killington Ski Area family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite

Guesthouse in Randolph

4.96 out of 5 average rating, 256 reviews

Macintosh Hill Farm

VinnyRating, 5 stars1 week ago
Came up to VT for a ski trip and the air bnb was a perfect base camp. Cozy and quiet. It was the perfect place to recharge and get back to the mountains. Hot tub was awesome with a spectacular view! Would go back!
Guest favourite

Chalet in Killington

4.83 out of 5 average rating, 243 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

NolanRating, 5 stars2 weeks ago
Great place for a vacation stay with friends or family. Hot tub was a nice bonus in the winter after long days skiing. Plenty of sleeping space, clear instructions for everything you’d need in the place
Guest favourite

Chalet in Ludlow

4.95 out of 5 average rating, 121 reviews

Okemo Ski Chalet with Hot Tub

ScottRating, 5 stars6 days ago
Bob was wonderful and very helpful and responsive during the whole trip. The house was also great and had more than enough space for all of the members of my group. I would very gladly stay there again in the future!
Superhost

Home in Pittsfield

4.83 out of 5 average rating, 233 reviews

Killington area home - 4-seasons & hot tub

RobertRating, 5 stars1 week ago
Good house overall. Pool table and hot tub were fun. Close to Killington. Fire pits were nice. David was great to communicate with.
Guest favourite

Condo in Ludlow

4.92 out of 5 average rating, 101 reviews

One Bedroom Suite Near Okemo

ScottRating, 5 stars1 day ago
Wonderful ski weekend at Okemo. Everything was perfect. We would definitely stay here again. Highly recommend!
Superhost

Chalet in Stockbridge

4.92 out of 5 average rating, 178 reviews

Killington ski house winter MTbike -new jacuzzi

MichelleRating, 5 stars2 months 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 favourite

Chalet in Killington

4.87 out of 5 average rating, 245 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

KerryRating, 5 stars2 weeks ago
We had a wonderful stay at Cammie’s house! It was more than enough space for 2 families of 5 to spread out! The kids really enjoyed foosball and ping pong. The adults really enjoyed sitting by the fire. The walk to the ski trail was a little tricky as the path was not well traveled and the snow was deep. The walk home from the trail was much easier. One small suggestion would be to have more mugs and more wine glasses available. Overall, a fantastic long weekend!
Guest favourite

Cabin in Ripton

5 out of 5 average rating, 103 reviews

#7 - Hemlock Hideaway Cabin

ShanaRating, 5 stars1 month ago
Just perfect! Hemlock Hideaway was a great place to recharge. Carol & Marty have thought of everything, and the cinnamon twists the first morning are amazing! We already booked our return trip :)

Family- and pet-friendly home rentals

Superhost

Cabin in Cavendish

4.95 out of 5 average rating, 153 reviews

The Cozy Little Red Cabin

BrookeRating, 5 stars2 weeks ago
We enjoyed our stay. Location was perfect! Cabin was cozy with movies and games to keep us entertained when not on the slopes
Superhost

Apartment in Middlebury

4.79 out of 5 average rating, 184 reviews

Downtown Middlebury 3 BR Home - Walk Everywhere!

DanielleRating, 5 stars1 week ago
The Airbnb is perfectly located next to everything in town. Comfortably slept 6 of us and I could easily see fitting another person. Kitchen was fully stocked and had a perfect little space for the group gathering.
Guest favourite

Cabin in Woodstock

4.95 out of 5 average rating, 198 reviews

Hideaway Cabin by the Stream on 27 Acres

JordanRating, 5 stars5 months ago
We had an awesome getaway at Kevin and Lesley’s cabin! This was our last little getaway before we get married this fall and it was the perfect unplugged retreat to feel connected going into the stressful time before the wedding. The cabin is cozy, the bathroom is adequate and sort of surprisingly not as buggy as it could have been, and the porch was my favorite spot to feel connected to nature. Kevin was very communicative and the instructions in the cabin were very clear. Luce’s lookout was amazing at the top and a really great recommendation by our hosts. We would definitely go back!
Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 246 reviews

Hancock hideaway

EliottRating, 5 stars6 days ago
Heidi‘s cabin is lovely. We went for a snowboarding trip, it’s situated perfectly between Killington and Sugarbush. Would definitely stay again.
Guest favourite

Home in Goshen

4.83 out of 5 average rating, 283 reviews

Nature Lover's Paradise

NathanRating, 5 stars3 weeks ago
Had a fantastic time. Went backcountry skiing before work and then worked from his place with multiple people doing zoom calls without issues. Perfect place for us
Superhost

Home in Hancock

4.77 out of 5 average rating, 105 reviews

Sugarbush 1880s Farmhouse - With Scenic Views 5/2

MelissaRating, 5 stars5 months ago
This place is exactly as described.. not luxurious, old style farmhouse with lots of charm. Plenty of space for many people, with 2 living room areas plus an upstairs with sleeping quarters.. laundry and kitchen. The road is exactly as Bethany describes… but not so busy that you feel like you’re on a main route. Beautiful scenery.. close to the town we had a family wedding in. Many local attractions nearby. A couple hiccups, but nothing unexpected in an old house and Bethany was responsive and very happy to get feedback. Tons of linen, kitchen accessories and windows to let the fresh air in. The home has beautiful old charm, could use some upgrade in furniture but otherwise great place and we’d rent again. Bethany was flexible for check out abs reasonable
Guest favourite

Home in Rochester

4.98 out of 5 average rating, 203 reviews

The Guest House at Sky Hollow

MargaretRating, 5 stars1 month ago
The house more than met our expectations! We skied at Killington and Sugarbush and snowshoed on trails behind the house. The house was very cozy and quiet with a large kitchen and very cozy spots to read and sleep in after a long day of being outside. I highly recommend staying here!
Guest favourite

Cabin in Pawlet

4.93 out of 5 average rating, 146 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

AndrewRating, 5 stars1 week ago
Hands down the coolest Airbnb I have ever stayed in. Plus, Rik was a great host! Will definitely be back again

Family-friendly home rentals with a pool

Guest favourite

Guest suite in Killington

4.95 out of 5 average rating, 142 reviews

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

VickiRating, 5 stars2 weeks ago
This place was great! Nothing fancy but a great price and plenty of room for me and my friends. Exactly as photographed and described. Foster is also a very nice man! Super friendly. Would definitely recommend and stay there again!
Guest favourite

Condo in Killington

4.95 out of 5 average rating, 103 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

DarrenRating, 5 stars4 days ago
James was a great host, the place was very clean and VERY close the the ski trail. Would love to stay again some day!
Guest favourite

Guesthouse in Granville

4.9 out of 5 average rating, 875 reviews

Moon Valley Country Retreat no clean fee pets yes

MelissaRating, 5 stars4 days ago
We had a lovely stay. The site was as private as described, but we never felt Lorraine was unavailable or distant. She was terrific with all communication.
Superhost

Condo in Killington

4.8 out of 5 average rating, 105 reviews

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

DeniseRating, 5 stars2 weeks ago
Dray was great - immediate response to any questions. Finding the place and getting in was easy. Had everything you need - maybe could of used a couple extra towels. Beds were comfortable. Great stay!
Superhost

Condo in Killington

4.82 out of 5 average rating, 257 reviews

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

SamanthaRating, 5 stars3 weeks ago
We had a great stay, everything was as described! Jonathan was great, always got back to us immediately when we had questions and was really accommodating and helpful.
Superhost

Condo in Killington

4.78 out of 5 average rating, 298 reviews

Serene Top Floor Condo (resort style amenities)

JamesRating, 5 stars2 weeks ago
Can't think of anything to add to all that's been said in the 5 star reviews! Scott was great to deal with and will absolutely stay again
Guest favourite

Condo in Killington

4.96 out of 5 average rating, 137 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

JennyRating, 5 stars1 week ago
Perfect location for our weekend ski trip to Killington, about a 10 min walk to Snowshed Lodge area and a ski home trail right to the building. The condo is well outfitted and spacious, with newer mattresses. We didn't get a chance to use the sauna, but everything was very comfortable.
Guest favourite

Condo in Killington

4.93 out of 5 average rating, 437 reviews

Pico Ski in out 1 bedroom 1 nite Ok free shuttle

ChristineRating, 5 stars1 week ago
Gabe's place was great for our ski weekend at Killington and Pico. A spacious place for our family of four and the kitchen had everything we needed. Super convenient ski location for Pico and a short drive to Killington. Would definitely look to stay again!

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