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

Guest favorite

Guesthouse in Randolph

4.96 out of 5 average rating, 253 reviews

Macintosh Hill Farm

LonnyRating, 5 stars1 week ago
Whatever search parameters led you to this listing, it's most likely exactly what you're looking for. Quaint and cozy, with an ambiance that screams Vermont. The hot tub under the stars is an experience all its own. We sat warm and comfortable in the middle of a snowstorm with icicles forming in my beard. Perfect, all around.
Guest favorite

Chalet in Killington

4.83 out of 5 average rating, 242 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

JoeyRating, 5 stars3 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

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!
Superhost

Condo in Ludlow

5 out of 5 average rating, 11 reviews

3 Bedroom Castle Town Home

PatrickRating, 5 stars2 weeks ago
We were very happy with Andy’s place and will use it again. It’s Well laid out and spacious with a lovely ski house decor. The extra space in the loft area for TV and a second sitting room with a small kitchenette and TV is great for families .
Superhost

Home in Pittsfield

4.84 out of 5 average rating, 231 reviews

Killington area home - 4-seasons & hot tub

KerryRating, 5 stars1 month ago
David's place is amazing! It is very comfortable and clean with plenty of room. The outdoor hot tub is very clean and a great perk. David was very responsive and we are grateful that he allowed us an early check-in and later check-out. The house is well-maintained and fully stocked for everything we needed.
Superhost

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 stars1 week ago
Cammie was a great host. She was very responsive and helpful
Guest favorite

Cabin in Ripton

5 out of 5 average rating, 102 reviews

#7 - Hemlock Hideaway Cabin

ShanaRating, 5 stars3 weeks 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, 150 reviews

The Cozy Little Red Cabin

JohnRating, 5 stars2 weeks ago
My wife and I very much enjoyed our stay at the cozy red cabin. We very much appreciated the wood stove and stock of firewood with the subzero Temps outside. The kitchen had everything we needed. It is a quick 15 minute drive to Okemo so a wonderful alternative to a pricey condo there. Thanks Marina we hope to be back again.
Superhost

Apartment in Middlebury

4.79 out of 5 average rating, 183 reviews

Downtown Middlebury 3 BR Home - Walk Everywhere!

tomRating, 5 stars6 days ago
quaint and quiet. nice Spot in a beautiful town. love the village feel of the house and the town.
Guest favorite

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 favorite

Cabin in Hancock

4.95 out of 5 average rating, 242 reviews

Hancock hideaway

OliviaRating, 5 stars1 month ago
Heidi was so responsive, helpful and accommodating! The place is stunning and so cozy in winter. Couldn’t get over the view and the location was great - so close to so many trails and cute spots!
Guest favorite

Home in Goshen

4.83 out of 5 average rating, 283 reviews

Nature Lover's Paradise

NathanRating, 5 stars4 days 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

4.78 out of 5 average rating, 104 reviews

Sugarbush 1880s Farmhouse - With Scenic Views 5/2

MelissaRating, 5 stars4 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 favorite

Home in Rochester

4.98 out of 5 average rating, 202 reviews

The Guest House at Sky Hollow

EricaRating, 5 stars4 weeks ago
My family and I LOVED our stay! The cottage is incredibly cozy and well appointed. Jess is a fantastic host and made us feel so welcome. She was incredibly kind to our son who absolutely loved the farm and all of the animals. Jess’ dogs were also great hosts playing with our own dog every day. We are already looking forward to our next trip!
Guest favorite

Cabin in Pawlet

4.93 out of 5 average rating, 143 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

AvaRating, 5 stars2 weeks ago
Me and 3 friends stayed in Rik’s place for the weekend to celebrate my birthday! Instantly we were blown away by the craftsmanship of the house. The details were stunning and we were wowed at every turn. The bathrooms were truly unbelievable and unexpected in the best way! Rik greeted us with the most delicious fresh rosemary bread that we devoured. The kitchen was fully stocked with cast iron and stainless steel pans. We already are planning on coming back in the warmer months to experience the property in a lush state. If you visit in the winter months, check out the tree houses on the property. Thanks for a great weekend Rik!!!!

Family-friendly home rentals with a pool

Guest favorite

Home in Granville

4.96 out of 5 average rating, 135 reviews

Epic Views of the Green Mountains

JamesRating, 5 stars1 week ago
This was a great stay for us! We stayed at the Broadloaf Mountain Cottage during the winter so we could do some snowshoeing and winter hiking. The cottage itself was just as described and the views are difficult to describe but in a word, 'Majestic'. The location is remote but that is what we were looking for. Access to grocery stores, restaurants, etc. are about 25 minutes away which was fine for us. William's hospitality was second to none. On our arrival he had already stopped by and even prepared some kindling for the woodstove. As we were unfamiliar with the area, William even stopped by one morning to chat and point out some locations for use to try. This was extremely helpful and his recommendations were spot on for what we were looking for. We'll look forward to returning again for certain.
Guest favorite

Guest suite in Killington

4.95 out of 5 average rating, 141 reviews

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

ShaynaRating, 5 stars3 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.
Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 869 reviews

Moon Valley Country Retreat no clean fee pets yes

OliviaRating, 5 stars1 week ago
I’m proud to say this is my third consecutive year visiting Loraine’s Moon Valley BnB and it’s such a great experience each time. I visit in the winter and always walk in to a cozy fire in the wood stove, a welcoming note on the chalkboard, and the space being clean, inviting, and peaceful. Loraine is always responsive and helpful, and provides a wealth of resources and recommendations for your stay. The space is pet-friendly, and my dog and I especially enjoy walking the nearby snowmobile trails up the mountain. Considering Loraine doesn’t require a pet fee or cleaning fee, the space is kept in wonderful condition. You can tell she truly cares about your time there.
Superhost

Condo in Killington

4.8 out of 5 average rating, 103 reviews

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

KristinRating, 5 stars1 week 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, 256 reviews

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

SamanthaRating, 5 stars3 days 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, 294 reviews

Serene Top Floor Condo (resort style amenities)

CaseyRating, 5 stars3 days ago
Perfect place for a weekend getaway at Killington! Scott’s place is steps from the mountain making it very convenient for a weekend of skiing. The apartment is comfortable, clean, and very well appointed! Health club in the building is a nice addition for relaxation at the end of the day (pool, hot tub, saunas). Scott was a fantastic and responsive host. We’d definitely come back!
Guest favorite

Condo in Killington

4.96 out of 5 average rating, 134 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

ThomasRating, 5 stars5 days ago
We really enjoyed our stay here and it was the perfect place for our annual ski trip. Alexandros provided really helpful information ahead of time so we knew exactly what to expect when we arrived for check-in. The place was very clean and well stocked for our arrival. One of the best features of this accommodation is the ski-in access directly from the mountain. That was a great way to end our ski day. Overall, we would definitely recommend this place to others.
Guest favorite

Condo in Killington

4.93 out of 5 average rating, 430 reviews

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

BurcinRating, 5 stars1 week 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!

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