Ski-in/Ski-out holiday rentals in Connecticut River

Mountainside - Ski In/Out Condo

You'll be close to everything in this modern condo. Top of Mountainside Road - walk 1 min to the trail & ski down to Whiffletree lift. Easy to stop for lunch or quick warm up. Après - stroll down to the Village for food & fun! 3 bedrooms (2 queen beds & 4 bunks) Open Kitchen, living & dining room w/ fireplace. Large mudroom for all your gear. Deck overlooking Bigelow Range. Last 6+ years 4.9 star reviews & managed by rental agent. Now Book direct with owner, a Sugarloafer since 1977!

The Lil’ Chalet-Assoc. Beach-NO Cleaning Fee!

This unique "Arched Cabin" is located on the side of Pleasant Ski Mtn off of Rabbit Run Trail. Summer Private Association beach access! Creatively built with local hewn pine boards and radiant heated flooring, this Lil' Chalet has been designed with a spirited and eclectic ski theme through out. Only steps from Bridgton's best skiing and hiking, this 1st floor walk out is 30 min to N Conway eats/ski/shopping and 7 min to the sweet village of Bridgton. Local favs/Association Beach access😎

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

Post & Beam, Ski-in/Ski-Out Birchwood Penthouse

Editors choice!! Located in the heart of the action!! Beautiful post and beam, ski-in/ski-out Birchwood penthouse perfect for a family and friends getaway. Sleeps 10. Fantastic views of the mountain as well as the Bigelow range. Minutes walk (or ski) to the best that Sugarloaf has to offer: Sugarloaf Village, Upper Snubber trail and lifts (Sawduster), Shipyard Brew Haus, Sugartree Sports & Fitness Center with indoor pool, indoor and outdoor hot tubs, steam room, sauna and more!

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.

⭐️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

Pet friendly condo - come visit for the summer!

This centrally-located condo offers proximity to various amenities. Ski in-Ski Out, Equipped with a full kitchen, bathroom, flat-screen TV, ski locker, Wi-Fi, and more, this condo ensures a comfortable stay. Step outside to find the ski lift conveniently located just outside the door. Suitable for 2 adults, guests can enjoy post-skiing drinks at the Sugarloaf BrewHaus within walking distance or the Sugarloaf Fitness Center across the street (for a fee). Dog friendly!

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.

Ski-in, Ski-out Timbers 4-Bedroom condo

This Timbers location cannot be beat: ski-in, ski-out, only a 5 minute walk to base village and right next to the Superquad! Newly furnished and stylishly decorated, this family-friendly 4 bed, 3 bath Timbers condo features an open-concept main floor with living area, kitchen, and dining table for 10. Well-stocked kitchen and TV for each bedroom. Upstairs has 3 BR, 2 BA and basement has ski prep & rec area, additional bathroom and bunk room.