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Ski-in/Ski-out vacation rentals in Hancock

Find and book unique ski-in/ski-out homes on Airbnb

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Popular amenities for Hancock ski-in/ski-out rentals

Ski-in/ski-out house rentals

Superhost
A tranquil exterior view of a single-story house, framed by lush greenery and vibrant flowers. A gravel path leads to the front door, which is flanked by a small set of stairs. Two satellite dishes are visible on the roof among the trees.
Home in Stephentown
4.8 out of 5 average rating, 76 reviews

A Magic Spot: Booking year round.

PhilRating, 5 stars6 months ago
the airbnb is very homey, well stocked, and easy to navigate. we had one slight issue with a mess that was not found by the cleaning crew, but robert was friendly and shared our concern about this.
Home in Ancramdale
4.86 out of 5 average rating, 7 reviews

Family-Friendly Home on a Private Lake

PatriciaRating, 5 stars6 months ago
We spent 3 nights at Jeens house and our kids (2.5 and 4 years) were in paradise. Great place for families as main rooms are all on ground floor and the basement is great for more kids entertainment. Best feature is the sun room - makes all the difference! Would have liked a more comfy couch here, but that’s a minor thing. It is very quiet around the house but there are neighbors next door, just that you know. Not sure if I’d be missing a bigger deck in the summer - even now at a sunny October day we would have loved a deck to spent time outside. There are many things to do and see all around and Jeens recommendations were great! Love that everything is layed out in the handbook - very helpful. We’ve also had the problem with the smelly (fishy) fridge, hope they get that solved until their next guests arrive. All in all we had a great stay at the house and would always come back! Oh and we saw so many animals from out of the window including deer - great experience!
An inviting living space features rich wooden beams and polished hardwood floors. A comfortable chair and a dining table are visible, accompanied by four chairs. Natural light floods through large windows, illuminating a vibrant area rug and a simple arrangement of fresh flowers.
Home in Canaan
5 out of 5 average rating, 11 reviews

Knoll Rock House (3B/3B) - Best of the Berkshires

AlexanderRating, 5 stars46 months ago
Absolutely fabulous AirBNB. Super beautiful spot, close to Tanglewood. Amazing kitchen and bathrooms, beautiful antiques, quiet secluded spot but near all the best of the Berkshires. Mai was very helpful with local tips and folding chairs and all. Thank you for a great stay, we look forward to returning!
An outdoor deck features a hot tub with steam rising above, surrounded by snow-covered wood. A fire pit with flickering flames adds warmth, while a distant view of ski slopes is visible in the background, framed by sparse trees.
Home in Hancock
4.83 out of 5 average rating, 12 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

LindaRating, 5 stars2 months ago
This home was the perfect place for our family/friends gathering. Location was fantastic - just a short 1-2 min walk to the ski-in spot, making it incredibly convenient for hitting the slopes with little ones. The host was exceptionally informative and friendly, ensuring we had everything for a comfy stay. Kids had fun sledding between the houses and grownups loved the hot tub.
Guest favorite
A snow-covered landscape is visible, with trees lining the sides of a roadway. The hills in the background are partially obscured by clouds, suggesting a serene winter atmosphere. Several homes and parked cars can be seen along the road.
Home in Hancock
4.95 out of 5 average rating, 22 reviews

Condo on the mountain

NicholasRating, 5 stars3 months ago
Lovely one night stay! Perfect location on the mountain, super clean and Zaighum was very helpful and accommodating with an early check in. Would highly recommend!
A rustic wooden home is surrounded by snow-covered ground and towering evergreen trees. A clear blue sky can be seen overhead, and the wide driveway leads to the entrance, showcasing the home’s inviting architecture under a blanket of winter snow.
Home in Woodford
4.7 out of 5 average rating, 10 reviews

Serene getaway in the Vermont National Forrest

BrianRating, 5 stars43 months ago
Great location, 30 min from MASSMOCA. Beautiful home and property. Lots of room. We had two families with kids and had a great time.
Top guest favorite
A cozy living area showcases a large sectional couch and a brick fireplace. Natural wooden paneling adorns the walls, while light reflects off the hardwood flooring. A spacious dining area is visible in the background, with a large table and elegant lighting.
Home in Wilmington
5 out of 5 average rating, 24 reviews

Rustic home near skiing & lakes, walk to downtown

MichaelRating, 5 stars1 month ago
We had a great stay at Dennis’s place. Everything was prepared and perfect upon arrival. We also appreciated the attention to having plates, pot, pans, etc. made it a lot easier than most I’ve stayed at.
Home in Troy
4.75 out of 5 average rating, 113 reviews

Riverfront Rustic 1824 Mansion

BrookeRating, 5 stars1 month ago
One of our favorite stays so far. The place has character for days, with enough modern amenities for comfort. The lived-in feel had us settling in in no time. Beds were comfortable enough - the pull-out sofa beds less so, though I've yet to meet one that was otherwise. Everyone adored the balcony. The kitchen was better equipped than any other airbnb I've stayed in by a long shot. We wished we had more time to spend out on the deck and the lovely lawn stretching down to the water. Hope to return in the summer or fall someday!

Family-friendly, ski-in/ski-out home rentals

A historic farmhouse is nestled in a peaceful farmland setting, surrounded by lush greenery and towering trees. The white exterior features a welcoming front porch, and solar panels are visible on the roof. A well-maintained lawn adds to the tranquil atmosphere.
Home in Craryville
4.84 out of 5 average rating, 49 reviews

Diamond in the Rough

KathleenRating, 5 stars17 months ago
My family and I had a great time at Delana’s lovely house Craryville is a beautiful place We love staying at Delana’s place and hope to come back for our Thanksgiving holiday next year! Thank you very much
Superhost
An old agricultural tool sits in a grassy field, its wheels complementing the expansive landscape. In the background, vibrant hues of sunset illuminate the sky, casting a soft glow over the lush green foliage and distant hills.
Guest suite in Lee
4.74 out of 5 average rating, 197 reviews

Berkshire Charm w/ Panoramic views

KadeeRating, 5 stars6 months ago
Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.
Guest favorite
Hotel room in Hancock
4.87 out of 5 average rating, 15 reviews

Wyndham Bentley Brook ** 2BR Deluxe

KateRating, 5 stars1 month ago
This was a great place to stay as a family for a ski trip! Easy ski on/ski off access to the mountain with ski lockers was a huge plus. Easy enough to walk to a few restaurants. The kids love the movie theater, pool and game room. Very clean and friendly/helpful staff at front desk.
Guest favorite
The wooden cabin is enveloped in a serene winter landscape, with smoke rising gently from the chimney. Snow blankets the ground, and trees dot the backdrop. A front porch extends along the cabin, providing a welcoming entrance. A snowmobile is parked nearby.
Cabin in Woodford
4.98 out of 5 average rating, 145 reviews

Stone's Camp on Stamford Stream

ThomasRating, 5 stars6 months ago
This was our second stay at Stone's Camp. It was just as great as the first stay. It's very private, peaceful and relaxing. We enjoyed hiking around the area and never had to leave the property in our car during our 4 night stay. The walk from the camp down the abandoned road to the washout is perfect. Our dogs enjoyed being off leash and exploring the woods and stream. It was especially nice for our 15 yro dog who is now unable to tackle larger hikes. Nights were spent enjoying a campfire by the babbling stream on rain free nights. Rainy nights were spent playing cards and games around the table indoors. If you are looking for something quiet, private and love to be outside and away from it all this is the place for you. If you have dogs it's the place for them as well. Thank you again, Chuck, for sharing your piece of paradise and thanks for accommodating our daughter and her boyfriend at the last minute who surprised us with a visit from the West Coast. We hope to be back!
Superhost
An interior space features rustic wooden walls and a wooden floor, illuminated by natural light through a window. A picnic-style table sits centrally, while dart boards are mounted on opposite walls. Additional seating is provided by several wooden chairs in the room.
Home in Whitingham
4.93 out of 5 average rating, 70 reviews

The Amos Brown House.

PeterRating, 5 stars2 months ago
This is a really special antique house that has been very well cared for. we visited in the midst of pretty narly presidents dy snow storm and the howling winds and multiple feet of snow outside only made the old house feel even cozier and more special. in the winter, the house sits on the end of a dirt road, due to the southern portion of it being covered in snow so we were nervous that we would get completely snowed in, but the town plowed the road multiple times each day and we had no problems getting in and out! Our big highlights were cross country skiing on the trail that crosses the property, puzzling by the gas fireplace, and the huge mounds of dog toys for our pup! Also, big thank you to Michelle for being so accommodating about our late check out. Our time here makes me want to check out all of the landmark trusts locations!
Hotel room in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook * Studio

LaurelaRating, 5 stars50 months ago
We had such a great time at Rob&Julia's place. Very good communication, great location, the place was sparkling clean! I will definitely come back again with my family! One of my best experiences
Guest favorite
A guest room features a twin bed with a quilted coverlet and a decorative mirror on the wall. A plaid armchair and a bench are positioned near two windows, allowing natural light to illuminate the space. A braided rug adds texture to the floor.
Private room in Claverack
4.92 out of 5 average rating, 108 reviews

Peaceful Solar Home

AriahRating, 5 stars4 months ago
This was our second time staying with Betsy. She has been incredibly accommodating for myself and my toddler. My daughter loves staying at “Tigger’s house” (Tigger is Betsy’s very well behaved friendly dog.)
Guest favorite
The exterior of a wooden lodge is visible, showcasing large windows that reflect the serene winter landscape. Snow carpets the ground, and a lone adirondack chair is positioned nearby. A distant view of rolling hills and trees is framed by a bare tree branch in the foreground.
Home in Hawley
4.95 out of 5 average rating, 38 reviews

Stump Sprouts Lodge

PaulRating, 5 stars5 months ago
We gather with a large group of friends every year and this was an ideal location for our reunion. There is plenty of space to spread out, a well-equipped kitchen, and a spacious dining area. There are wonderful trails to hike (or ski later in the season)

Ski-in/ski-out condo rentals

Guest favorite
An outdoor hot tub is located under a wooden gazebo structure, surrounded by wooden slatting. Two lounge chairs are positioned nearby for relaxation. The backdrop features softly lit resort buildings, with lush greenery and a hillside visible in the distance.
Condo in Hancock
5 out of 5 average rating, 8 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

JoelmaRating, 5 stars4 months ago
Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.
Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.95 out of 5 average rating, 57 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

JenniferRating, 5 stars1 month ago
We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!
Superhost
A wooden gazebo encloses a hot tub, providing a relaxing space with soothing water movement. Wooden lounge chairs are positioned nearby, and the background features the resort buildings softly illuminated in the evening light, surrounded by greenery.
Condo in Hancock
5 out of 5 average rating, 5 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

MaryRating, 5 stars2 months ago
We had a wonderful stay at Jiminy Peak.. hosts were super quick to respond with any questions. Very easy check in and check out. Will definitely be staying again in the future!
Condo in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars15 months ago
We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+
Superhost
A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.
Condo in Hancock
4.87 out of 5 average rating, 31 reviews

Jiminy Peak Apartment

SandyRating, 5 stars2 months ago
Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.
Superhost
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars14 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!
Guest favorite
A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.
Condo in Hancock
4.92 out of 5 average rating, 65 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

MeganRating, 5 stars6 days ago
Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.
A snow-covered landscape features a brightly lit Christmas tree at the center, surrounded by benches and twinkling lights. Buildings with illuminated windows create a cozy atmosphere, while gentle snowfall adds a touch of winter charm to the scene.
Condo in Hancock
4.9 out of 5 average rating, 10 reviews

Ski-in/Ski-Out on Jiminy Peak

BiancaRating, 5 stars2 months ago
Perfect home base for skiing at Jiminy! It was great for me and my kid plus we got to enjoy the hot tub, pool, breakfast at the country store and dinner at bluebird & co. Justine was a great and communicative host - we hope to return soon!

Quick stats about vacation rentals that are ski-in ski-out in Hancock

  • Total rentals

    60 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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