Ski-in/Ski-out vacation rentals in Bolton

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

Top-rated ski-in/ski-out rentals in Bolton

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Superhost

Home in Warren

4.82 out of 5 average rating, 117 reviews

Charming Sugarbush Standalone Condo

Situated on the mountain with a panoramic view, this stand alone condo - ski-on/ski-off (winter) / spectacular vistas (fall) / Mad River fun (summer) / blissful bloom (spring) - will be your home away from home. This spacious, three-floored home is filled with light and great for couples, families, business travelers, or solo adventurers. Friendly property manager, Constancia is able to greet guests and offer recommendations. Please find our cleaning protocol in "Other things to note" section.

Guest favorite

Condo in Cambridge

4.94 out of 5 average rating, 153 reviews

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

Smugglers Notch Resort ⭐️ Ski-in/out location Exit the front doors of complex, turn left and cross the small lot to pick up trail leading down to the lift :) • no shuttle bus needed • ground floor unit - 480 sq/ft. • private deck • fully stocked and equipped kitchen • bike/walk/hiking trails Add listing to your wishlist by clicking the ❤️ in the upper right corner. **SMUGG’s CHARGES A DAYPASS AT FRONT DESK FOR USE OF POOL, HOT TUB & FUNZONE** *Drip coffee pot has reusable Mesh Filter.

Guest favorite

Condo in Rutland

4.94 out of 5 average rating, 107 reviews

Ski on Ski off killington/ Pico mountain condo

Beautiful ski on ski off condo at the foot off Pico mountain ski resort. Free shuttle bus to Killington and Rutland at front door. 4th floor (top floor) condo with elevator. Balcony with view of Dears Leep overlook. Quiet top floor end unit. Full kitchen, 1 bedroom with seperate living room. Living room has pull out sofa bed and 54 inch t.v. and WIFI. Hike the Appalachian, Long and Catamount trails from your back door. Ski locker on ground floor. Please be sure to read and agree to house rules.

Guest favorite

Condo in Jay

4.92 out of 5 average rating, 160 reviews

Ski in Ski out - fantastic location on the trail

This condo lies in the heart of the original Jay Village, offering flexible living space for a family or group of friends. With 2 bedrooms and 2 bathrooms, everyone can have the space that they need. Access via private entrance with a mud room for leaving all the outdoor gear, in summer and in winter. Enjoy free parking, outside space and a balcony with a serene view into the woods. Make the most of the resort activities (Water park, pool, golf, ice rink) for a fee to the resort.

Guest favorite

Condo in Warren

5 out of 5 average rating, 24 reviews

Sugarbush ski in/out condo with seasonal pool

Enjoy this ski-on/ski-off, stylishly renovated mountainside condo; literally steps to the ski-on/off trail. The space is perfect for guests who enjoy uber-convenient access to the slopes and great aprés ski options, including the famous Chez Henri Bistrot. Take advantage of our heated pool for guests during the summer months. There are stunning mountain views from the living room and private balcony. Mountainside Ski Service is right downstairs for those last minute tune-ups.

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 105 reviews

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

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

Guest favorite

Apartment in Jay

5 out of 5 average rating, 7 reviews

Absolute best ski on/off at Jay.

Location, location, location. This 2br Slopeside condo is position A on the snowiest mountain in the east. Inside, you'll find 2 bedrooms featuring a queen bed and a twin over full bunk. The kitchen comes fully equipped to make meal prep a breeze. The cozy living room has a gas fireplace to warm up or relax and enjoy an après drink. Our condos always feature complete linens, towels, and essential sundries because no one wants to lug that stuff to their vacation.

Guest favorite

Condo in Killington

4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Superhost

Condo in Jay

4.9 out of 5 average rating, 48 reviews

True Ski-in Ski-out! Walk to hotel-waterpark-golf

This is the perfect mountain spot all-year-round! “The Shredquarters” is a true ski-in-ski out condo with a fully fitted kitchen, new furniture throughout, free Wi-Fi, in unit dryer and washer, a WFH desk setup, and more! Easy access to all, it’s a three minute walk to the hotel restaurants, spa, and pump house water park and ice rink, and a 7 min walk/2 min shuttle to the golf course. There is A/C for the summer and a cozy gas fireplace in the winter.

Guest favorite

Home in Warren

4.92 out of 5 average rating, 49 reviews

Ski in/out 3 Bedroom/3 Bath Sugarbush

Wonderful ski-on/ski-off location (natural snow needed) with exclusive and convenient access to Sugarbush Resort's Cat's Meow trail. Renovated 3 bedrooms/3 baths - stand alone unit that sleeps 8. Beautiful wood burning fireplace with stacked wood right outside the front door. Enjoy all that winter has to offer in the Mad River Valley from this fantastic home. In the summer there is a shared pool and tennis courts for the entire family.

Superhost

Condo in Jay

4.78 out of 5 average rating, 36 reviews

Ski-in Ski-out 2bdrm condo, 3min walk to Waterpark

Ideally located Slopeside Condo overlooking the entire Tram Base Area and is within short 5 minute walk to the Tram House and all restaurants and amenities. Close to Racoon Run ski Trail (just cross the road). 3 minute trail walk to the Pump House Waterpark, Ice Haus Skating Rink and Golf Course Club house/Nordic Center. Direct access to Metro Quad and Flyer ski lifts.

Guest favorite

Condo in Warren

4.86 out of 5 average rating, 101 reviews

Sugarbush Mountainside Retreat - Ski in Ski out

Cozy and conveniently situated in the heart of Sugarbush Village, this recently renovated condo is a top floor end unit with views of the green mountains from every room. Regardless of the season you plan on visiting, this space is a perfect home base for all the Mad River Valley has to offer.

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What guests are saying

Ski-in/Ski-out Lodge Condo at Toll House Lift

4.86 out of 5 average rating, 36 reviews2 months ago

Loved that this was truly ski in/ski out! We were able to come back to the condo for lunch and then get right back out on the mountain. It was perfect! Condo is exactly as described. Kitchen is very well equipped, including a Panini maker! Loved the welcome bag of Vermont goodies! We had the best stay!

Condo in Stowe

What guests are saying

Cozy Ski-in/Ski-out Jay Peak Mountain Condo

5 out of 5 average rating, 37 reviews1 month ago

You can’t find a better place for ski in/ski out accommodations. Condo was perfect for our family of five with everything we needed. Easy walk right down the hill to food/the waterpark/apres fun. Our kids loved that they could literally pop on their skis and head right down to the lifts and I love that I could grab Ramen from the miso hut and then take the magic carpet right back up to the condo for lunch. We will definitely be back. Thank you so much!

Condo in Jay

What guests are saying

Jay Peak’s Premier Ski-in / Ski-out location!!

4.91 out of 5 average rating, 35 reviews3 weeks ago

Jennifer’s place was perfect for our family of four on a spring break trip to Jay Peak. Staying right on the Queen’s Highway was perfect for riding all day and close to pop in for a quick lunch break. We also loved walking to the Tramside restaurants for dinner.

Condo in Jay

What guests are saying

Ski in/Ski Out- Adjacent to Tram and Magic Carpet!

4.98 out of 5 average rating, 43 reviews1 week ago

Our family of four had a wonderful visit at Michael's condo! It is beautifully updated and welcoming. It is also in a perfect location for avid skiers. The condo is tucked into the corner of the building AND just a couple steps from the slopes! We loved the decor and how clean everything was. The appliances were practically brand new as were the dishes and cooking supplies. The beds were comfortable, the sheets and towels pristine. We would definitely recommend!

Condo in Jay

What guests are saying

Prime Ski-in/Ski-out @ PICO Mtn

4.97 out of 5 average rating, 29 reviews2 months ago

We had an amazing stay at Simone’s apartment for our ski vacation. The apartment was even better than the pictures—spacious, clean, and equipped with everything we needed. The location made skiing incredibly convenient, with easy in-and-out access to the slopes. The host was fantastic—super helpful, responsive, and easy to communicate with, which made everything smooth from check-in to check-out. The place had all the essentials and more, making it feel like a home away from home. Very thoughtful touches from the host through the apartment !!!! Highly recommend this place for anyone ( with kids, no kids) looking for a hassle-free and comfortable ski trip. We’ll definitely be back!

Condo in Killington

What guests are saying

Alpine Court Chalet: Ski-In/Ski-Out Escape Pico

4.86 out of 5 average rating, 14 reviews3 weeks ago

I'm almost scared to tell you all how perfect this little ski chalet was - how charming, how well-stocked, how clean, how well designed and well equipped - because then you might not leave any availability for me to return next year. Honestly, this house was exactly what we hoped for. So much more than what you expect from an Airbnb rental. Yes it was well prepared, well cleaned, stocked with all the supplies we needed - more than we had expected (never ran out of anything) - but it was also the charming personal touches - the ski memorabilia decorating the house, the Christmas lights and tree (even in April) - then there was the ample storage and shelves, the ski in/ski out mudroom to house all the ski gear, the hand-crocheted blankets to curl up with in the big comfy sofas - all of it made for the best vacation we could have hoped for. We had 5 people in our group - but it could comfortably house a bigger group. Just be sure to leave some time for us to return!

Home in Killington

What guests are saying

Studio Condo with the BEST Mountain Views!

4.96 out of 5 average rating, 48 reviews1 month ago

The location of Amanda’s condo at Smuggs is perfect. The lifts, village store and dining are all just a very short walk away. The condo has a great views of all 3 mountains and was clean and comfortable. Amanda responded very quickly to our questions and was always polite. If you want the convenience of ski-in / ski-out with easy access to the Village Center, I would recommend staying here.

Condo in Cambridge

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