Family-friendly vacation 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

Top guest favorite
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars2 days ago
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.
Guest favorite
Chalet in Killington
4.83 out of 5 average rating, 245 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

ShoshannahRating, 5 stars1 week ago
My family and i had a great stay. Everything was as it said and looked like in pictures and for what we needed, which was a comfortable, clean, roomy, mountain location, access road next to EVERYTHING, and affordable spot, it was perfect. The private hot tub and sauna were the deciding factor and they did not disappoint. The hot tub was so clean and top notch. We will def be going back there next time if available.
Guest favorite
Chalet in Ludlow
4.95 out of 5 average rating, 123 reviews

Okemo Ski Chalet with Hot Tub

RamonRating, 5 stars2 weeks ago
Pictures don’t do Bobs house justice, so much space for a big group, really well kept and lovely cosy and rustic feel. Loved the games room, hot tub and how isolated it was from surrounding properties. Bob was a great host - gave plenty of instructions and super responsive. No complaints!
Superhost
Home in Pittsfield
4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

KenleyRating, 5 stars1 week ago
We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!
Guest favorite
Condo in Ludlow
4.92 out of 5 average rating, 104 reviews

One Bedroom Suite Near Okemo

JunbaeRating, 5 stars1 week ago
It was a very nice and convenient place for our ski trip. The front staff were very helpful and the lobby area was also very cozy. We will use this place again for our ski trip to Okemo in the future.
Superhost
Cabin in Londonderry
4.82 out of 5 average rating, 460 reviews

Stunning Rustic Apple Barn - hot tub & sauna

LydiaRating, 5 stars3 weeks ago
Our stay at the Barn at Bent Apple Farms was truly a unique experience. My husband and I chose this spot for its proximity to Okemo and Mount Snow (only about 40 min to both of them), but we ended up enjoying the Barn as much as our time on the slopes! It’s clear that the owners put a lot of imagination into transforming this barn into a cozy retreat, and we’re grateful to have had the opportunity to stay here. I would highly recommend this location to anyone who wants an authentic countryside experience plus a few extra amenities like a modern kitchen and access to a hot tub.
Guest favorite
Chalet in Stockbridge
4.92 out of 5 average rating, 180 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars5 days ago
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend
Guest favorite
Chalet in Killington
4.87 out of 5 average rating, 246 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

KeithRating, 5 stars2 days ago
We had a incredible time enjoying the house and all it has to offer, and the proximity to town for restaurants. It was an awesome guys ski weekend and we’ll do it again next year.

Family- and pet-friendly home rentals

Guest favorite
Cabin in Cavendish
4.95 out of 5 average rating, 156 reviews

The Cozy Little Red Cabin

JohnRating, 5 stars2 weeks ago
We are very pleased to have chosen Marina‘s home. It was a perfect size for a small group, very comfortable and cozy, but also a nice spacious feel. The location is beautiful, especially in the winter time. Having the woodstove was an absolute plus and exceeded our expectations. Thank you for having us!
Superhost
Apartment in Middlebury
4.79 out of 5 average rating, 186 reviews

Downtown Middlebury 3 BR Home - Walk Everywhere!

KarenRating, 5 stars3 days ago
I felt immediately at home in Patrick's apartment in Middlebury. Loved the incredibly well-stocked kitchen, and the full-sized fridge was a real plus. Also loved the table for four in the adjoining room and the fact that there was a desk in that room, as I'd brought my laptop and needed to do some work. The bathroom was squeaky clean, with plenty of towels and an excellent tub/shower. Beds were exceptionally comfy, with nice linens and pillows. The fact that the apartment was within walking distance of town and the college was also a plus and made meeting friends extremely easy. I enjoyed my stay and would definitely return to Patrick's. Highly recommended.
Guest favorite
Cabin in Woodstock
4.95 out of 5 average rating, 198 reviews

Hideaway Cabin by the Stream on 27 Acres

JordanRating, 5 stars6 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!
Top guest favorite
Cabin in Hancock
4.95 out of 5 average rating, 245 reviews

Hancock hideaway

EliottRating, 5 stars3 weeks 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 favorite
Home in Goshen
4.83 out of 5 average rating, 283 reviews

Nature Lover's Paradise

NathanRating, 5 stars1 month 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, 106 reviews

Sugarbush 1880s Farmhouse - With Scenic Views 5/2

JonathanRating, 5 stars1 week ago
A cozy farmhouse with a lot of charm. Good for larger sized groups with the number of beds, as well as dual living rooms and two refrigerators. Highly recommend.
Guest favorite
Home in Rochester
4.98 out of 5 average rating, 203 reviews

The Guest House at Sky Hollow

MargaretRating, 5 stars2 months 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 favorite
Cabin in Pawlet
4.93 out of 5 average rating, 148 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

AnhRating, 5 stars3 days ago
Rik is a phenomenal host and made every detail of our stay fantastic from beginning to end, starting from the warm friendly greeting with thoughtful home-baked scrumptious bread to the intricate woodwork and stone sculpting details all throughout the cabin (and outside!). Our family (including our 2-yr old, 5-yr old + chihuahua) had a ton of imaginative wood forest / “stone cave” themed adventures both inside and outside the cabin - no need for TV cartoons or screens to keep the kids distracted with so much to explore! In addition to the lovely, quiet views as well as warm, cozy fireplace, the kids loved exploring the big, climbable sculpture before we trekked onward to the impressive tree houses nearby on the property. We normally do an annual winter Vermont cabin trip and this one far exceeded our expectations as rare find. Big thank you again for such a memorable experience for our family, Rik, and we look forward to visiting again soon!!

Family-friendly home rentals with a pool

Guest favorite
Guest suite in Killington
4.95 out of 5 average rating, 142 reviews

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

VickiRating, 5 stars1 month 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 favorite
Condo in Killington
4.95 out of 5 average rating, 103 reviews

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

DarrenRating, 5 stars3 weeks 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 favorite
Guesthouse in Granville
4.9 out of 5 average rating, 882 reviews

Moon Valley Country Retreat no clean fee pets yes

AdamRating, 5 stars2 days ago
This place is quite the find - both remote and charming. Friendly hosts who provided accurate instructions to the wood burning stove, etc.
Superhost
Condo in Killington
4.8 out of 5 average rating, 106 reviews

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

DeniseRating, 5 stars1 month 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

ZacharyRating, 5 stars2 weeks ago
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.
Superhost
Condo in Killington
4.78 out of 5 average rating, 302 reviews

Serene Top Floor Condo (resort style amenities)

NikosRating, 5 stars3 weeks ago
Scott is an outstanding host! His place is conveniently located next to the ski slopes, and he was incredibly responsive to any questions we had. Highly recommended!
Guest favorite
Condo in Killington
4.96 out of 5 average rating, 140 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

TaniaRating, 5 stars1 week ago
Alexandro was very helpful and proactive. We contacted him with a washer issue and he had someone come to fix it right away. Amazing ski on ski off accommodation!
Guest favorite
Condo in Killington
4.93 out of 5 average rating, 442 reviews

Pico April discounts 1 bedroom 1 nite Ok shuttle

KenRating, 5 stars2 days ago
Gabe’s condo was perfect for me and my kids on our ski trip. Very clean, quiet, and cozy. We loved the fireplace, plus the extra hand and toe warmers left out on the counter were a nice touch. We would definitely stay here again on future trips!

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