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Ski-in/out vacation rentals in Jiminy Peak

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

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Popular amenities for Jiminy Peak ski-in/out rentals

Ski-in/out house rentals

Superhost
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 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!
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 favourite
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!
Top guest favourite
Home in Wilmington
5 out of 5 average rating, 25 reviews

Rustic home near skiing & lakes, walk to downtown

JessicaRating, 5 stars1 week ago
We had a great time at this Airbnb! The game room was a selling point and it didn’t disappoint! The house was very spacious so everyone was able to have their own space if they wanted. The short walk to downtown was perfect and the town was so quaint and filled with friendly people! I would highly recommend this place we had an excellent time.
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!
Guest favourite
Home in Wilmington
4.89 out of 5 average rating, 27 reviews

Brand new, 5 BR, next to Hermitage Club&Hermt Inn

MargaretRating, 5 stars8 months ago
We loved this house! And plan to come back again soon! Beautiful home with great amenities. Host was very responsive. We had a great visit!
Top guest favourite
Home in Dover
4.98 out of 5 average rating, 52 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

JessicaRating, 5 stars1 month ago
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!

Family-friendly, ski-in/out home rentals

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
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 favourite
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 favourite
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
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 favourite
Townhouse in Mt. Snow, West Dover
4.78 out of 5 average rating, 40 reviews

Comfy Cozy Ski Townhome - Free Shuttle, Ski Home!

RyanRating, 5 stars2 months ago
Great place and amazing host! Very close to Mt Snow and easy mountain access with shuttle.
Guest favourite
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.)

Ski-in/out condo rentals

Guest favourite
Condo in Hancock
5 out of 5 average rating, 8 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

JoelmaRating, 5 stars5 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 favourite
Condo in Hancock
4.95 out of 5 average rating, 58 reviews

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

EladRating, 5 stars1 week ago
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.
Superhost
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
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.
Top guest favourite
Condo in Dover
4.86 out of 5 average rating, 14 reviews

Mount Snow Townhouse Dover VT 2BR, 2BA & Loft

LindsayRating, 5 stars1 month ago
Susan’s condo was perfect for our ski weekend! The condo was very clean and comfortable. The kitchen was really well stocked which made cooking our meals so easy. Susan communicated with us with very clear instructions for check in and out and responded quickly to questions. The location is great for visiting Mt. Snow. Our stay here was very enjoyable!
Superhost
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!!!

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