Ski-in/Ski-out holiday rentals in Rensselaer County

4.95 out of 5 average rating, 59 reviews

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

Jiminy's GEM is everything you're looking for! The location is absolutely prime- steps from the highspeed 6pk lift with your balcony overlooking the beautiful mountain & apres fire pit. Enjoy 3 bdrms/3 full baths with enough beds to accommodate numerous families, sleeping a total of 10 people. Take advantage of a heated pool, hottub & gym when you're not enjoying the mountain. Summer and Leaf Peeping season are equally as entertaining and enjoyable. Let us make your trip better than imagined!

4.98 out of 5 average rating, 44 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

4.92 out of 5 average rating, 13 reviews

Comfortable Berkshires retreat on mtn resort, SISO

Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a chalet: perfect after a ski/hike/bike through the beautiful mountains around it. 4 bdrs allow your group to space out, and a great room with 20 foot high ceilings extends through the dining area. Convenient to many Berkshires spots (Tanglewood, museums, etc.), a 2nd living room, fireplace, jacuzzi, and access to slopes, hot tubs, heated pool & gym complete the perfect getaway.

4.81 out of 5 average rating, 78 reviews

Home in Stephentown

A Magic Spot: Booking year round.

Winter (Skiing), Spring (1500 Tulips and Rare Lilies), Summer (It’s the Berkshires), and Fall (Autumn colors on the mountaintop): all you’ve got to do is call, and you’ll be here. Private/quiet. Art/books in every room. Hiking, birding, mushrooming. Nearby State Park for swimming. Near Tanglewood, Mass Moca, Clark Art Inst, Jiminy Peak. 2 bedrooms/$200, 3/$250, 4/$300. Summer Weekends $300 (Entire house.) summer AC surcharge $25/day if used. Discounts available. Excellent kitchen. Welcome Home!

4.91 out of 5 average rating, 92 reviews

Townhouse in Hancock

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Top guest favourite

Townhouse in Hancock

5 out of 5 average rating, 20 reviews

Serene+Stylish Mountain Retreat

Our beautifully-designed, comfortable, much-loved townhome is great for families or friends wanting an escape to the Berkshire mountains. Located up the hill from Jiminy Peak Village Center, the home has 4 bedrooms over 3 floors, an open plan living space, updated kitchen, family room, and new deck. A short walk to the slopes in winter and use of Jiminy Peak resort pools in the summer make it a year-round destination. Book your stay and find out why once you are here, it’s so hard to leave!

5 out of 5 average rating, 11 reviews

Flat in Hancock

Artsy loft near MassMoCA with pool and hot tubs

This ski-in/ski-out loft at Jiminy Peak offers all of the amenities you could ever possibly ask for! A spacious 1 bedroom loft that sleeps up to 4 (1 Queen Bed, 1 Pullout Couch) is stylish and comfortable. We are the new owners and we are regularly updating the furniture and decor. A full kitchen, full bathroom with tub, ski locker / equipment storage, laundry in unit, dedicated parking spot, access to 2 pools and 2 hot tubs, a sauna, skiing, mountain cart, ropes course, and more!

5 out of 5 average rating, 34 reviews

Cozy Cabin in Berkshires Resort

PERFECT COZY MOUNTAIN CABIN for a couple's getaway, a fun little trip with friends or with family to enjoy all offered by cultural Bershires in MA from outdoor activities, hiking, lake swimming, fun rides on the resort property, and music, performance, art and all cultural events. *** MOUNTAIN RIDES OPERATE FROM MEMORIADAL DAY WEEKEND THROUGH END OF SEPTEMBER ***Outdoor heated pool at Country Inn bldg stays open all year around when it’s above 25’F *** ONLY ONE PET ALLOWED **

4.96 out of 5 average rating, 24 reviews

Holiday home in Hancock

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

4.6 out of 5 average rating, 5 reviews

Flat in Hancock

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

The most fun Suite in the Berkshires - This gorgeous Gamers Suite will bring Families together Like No Other! No detail was missed in this adorable 1BR 1 BA Suite which Sleeps 4 comfortably with its King Bed and Pull out Queen Sofa in main room along with Kitchenette & Full Bath. Located in the BEST location At Jiminy - The Country Inn at the base of the mountain, you need to see this suite to believe it. Fully redone for Memories!

4.91 out of 5 average rating, 23 reviews

Large one bedroom, two full bath, full kitchen

Located in the heart of Hancock's premier ski-resort, Jiminy Peak this lovely appointed self contained apartment is ski on, ski off the 45 runs of the mountain. Perfect for a cozy Fall getaway to leaf peep all of the beautiful Berkshires. Close to Williamstown, North Adams, Lee, Lenox, Pittsfield and more. This is a year round spot with loads of activities. Pool, jacuzzi, exercise room and two restaurants are on site.

4.92 out of 5 average rating, 26 reviews

Family Lodge at Jiminy Peak - Pools & Adventure

Escape to the Berkshires this summer in our spacious 4BR/3BA townhome at Jiminy Peak! Perfect for families, with 2 living rooms, a fully equipped kitchen, and a large Trex deck with mountain views. Enjoy resort perks like outdoor pools, tennis, hiking trails, mountain coaster, and ropes course—all just steps away. With plenty of space and nonstop adventure, it’s the ultimate summer getaway for families and friends!

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Popular amenities for Rensselaer County ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

4.83 out of 5 average rating, 12 reviews

Beautiful 4 Bedroom Townhouse in the Berkshires

LindaRating, 5 stars4 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.

4 out of 5 average rating, 6 reviews

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Pe

AnthonyRating, 5 stars20 months ago

This place is worth every penny. Beautiful location on the mountain. Could not have asked for a better home to stay in.

4.88 out of 5 average rating, 24 reviews

Mountainside: Large 3-level Jiminy Peak Home

AmyRating, 5 stars4 months ago

We had an awesome time at Kathryn and Rob's condo. Kathryn was extremely responsive to my many questions, and flexible with timing. She asked ahead of time if we'd like to arrive early because of the impending snow storm which was very considerate. The house was clean and had everything we could possibly need. The kids (10,8, an 5) loved the basement foosball table and numerous board games, and the grownups enjoyed the many puzzles! The bed situation was perfect for spreading out so each person could have their own space. Kitchen was well-stocked and there really wasn't anything we needed that wasn't available. It looks even better in person than in the pictures. In addition, the location was super convenient for getting to the slope nice and early. Can't wait to come back!

LaurieRating, 5 stars8 months ago

Luxe Single-Fam Home, Jiminy Peak, Berkshires, MA

Jill was an absolute pleasure. Their home is absolutely beautiful, the pictures do not do it justice once you see it in person. They had more amenities in the kitchen than we expected, so I needlessly brought items that we didn't need. Unfortunately we had heavy rain during our stay, so our purpose of doing the activities at Jiminy Peak were a bust. However, our trip was saved with all the games they had in the den to occupy 6 kids without ANY complaints of boredom! 10/10 and will definitely book here again!

Home in Troy

4.75 out of 5 average rating, 118 reviews

Riverfront Rustic 1824 Mansion

TommyRating, 5 stars2 weeks ago

Had a great stay. It was quiet and had all that we needed while we were there. Would rent it again if I ever get back up to the area.

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Ski-in/out apartment rentals

5 out of 5 average rating, 8 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

JoelmaRating, 5 stars6 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.

5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars16 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!!!

4.9 out of 5 average rating, 10 reviews

Ski-in/Ski-Out on Jiminy Peak

BiancaRating, 5 stars4 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!

5 out of 5 average rating, 6 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

LaurenRating, 5 stars3 weeks ago

Hamilton is a wonderful host and the area is always beautiful and fun.

4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars17 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+

4.87 out of 5 average rating, 31 reviews

Jiminy Peak Apartment

SandyRating, 5 stars4 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.

KarenRating, 5 stars4 months ago

Condo Resort at Jiminy Peak Ski Mountain's Base

Hamilton was very responsive. The location was great and the resort was very family friendly.