Ski-in/Ski-out vacation rentals in Carrabassett Valley

Condo near wiffletree chairlift!

3bdr, 2 bath, 7bed. Sleep 10, perfect for 2 families! Steps from Wiffletree chairlift & MTN bike trails, near fitness center, restaurants & golf course. Out from the 70s, condo has nothing fancy, but has a LOT of heart & feels like 2nd home. 2 families (9 kids!) usually share it. Expect a fully functional place with many games. Bring your food, belongings & outdoor gear. Spend the day searching for powder & relax at night in front of the fireplace, where spirits of Amos Winter & Bob Marley meet!

Saddleback Chalet - Ski-in Ski-out

Ski in, ski out beautiful condo at on the highest road on Saddleback Mountain Ski Resort. Sun filled, 65” and 40” TV’s, extra playroom w couch. Two bedrooms furnished with one queen-size bed in each, and one bunk room with four twin-sized beds. Nice deck w amazing views of Saddleback Lake and beyond. Great place to utilize Saddleback skin trails. Come in the spring/summer for hiking the AT, biking & access to Trophy rivers for native brook trout fly fishing or Fall for unbelievable fall colors.

Spacious 4 BR Condo in Carrabassett Valley

Looking for direct access to adventure? This is it! Space for 10 means 2 families easily fit. Trail access is just a few steps away, straight to the super quad. Want to start slower? Try the shuttle to the village! Need to unwind at the end of the day? Downstairs family room provides large couch, tv, games, puzzles, etc for the kids while the adults enjoy some quiet time in the upstairs kitchen/living room. Hot tub to ease muscles at the end of an adventurous day! *hot tub closed May-Oct*

Cozy Ski-In/Ski-Out Escape at Sugarloaf with AC

Cozy ski-in/ski-out condo in Sugarloaf’s desirable Sugartree complex. Wake up, click in, and ski out. Enjoy effortless slope access, mountain adventures, and relaxing après ski memories. Perfect for families, couples, and outdoor enthusiasts year-round, with hiking, mountain biking, golf, and foliage outside your door. Mountain views from your private balcony, plus indoor access to the pool, hot tubs & sauna at the Sugarloaf Fitness Center (add’l fees apply). Full kitchen, and AC for summer!

Gondola Village at Sugarloaf

Welcome to the heart of Carrabassett Valley in the western mountains of Maine. Come golf, hike, bike, ski, and relax. Conveniently located at the bottom of Whiffletree chair (ski in, ski out) with views of Bigelow. Take a scenic chairlift ride or test out the new Sugarloaf Bike Park. Sugarloaf Golf Club is only minutes away. Enjoy miles of mountain biking, hiking, and cross-country trails. Short walk to base area for restaurants and shops. Then relax in this cozy condo after your adventures.

Ski-In Ski-Out Condo Perfect for Families!

Prime Location: Access the Condo Cross Cut trail right behind the condo, or take a leisurely 6-10 minute stroll to the Sawduster Chairlift and the popular Shipyard Brew Pub. Outdoor Space: Unwind on the porch after a thrilling day on the mountain. Fun for Everyone: Challenge your friends and family to a game of ping pong in the game area—perfect for friendly competition! Accommodations: Our 3 bedrooms and 3 bathrooms, plus a fun lower-level twin bunk bed, ideal for kids or extra guests.

Modern Ski and Golf - West Mnt

New in 2021 4BR townhouse at Sugarloaf! Hot tub and pet friendly. Walk to the West Mnt Trail or hop the free shuttle to the base lodge. Features a master king suite, 2 queen bedrooms, full guest bath. Basement has a teen retreat including a queen bed and bunkbeds, a private bath, and living room. Two living areas with big smart TVs, mountain views, and a fully stocked kitchen. Steps from golf, hiking, and biking trails. Perfect for families or friends looking for year-round mountain fun!

On-Mountain @ Saddleback-Hot Tub | Mountain Views

Welcome to the Last Chair Lodge - our family-friendly mountainside retreat at Saddleback Ski Area in Rangeley, ME. Custom, Maine-made Cedar Hot Tub! Incredible views - and sunsets - in all seasons. Ski-in/Ski-out in winter (natural snow dependent), in summer enjoy a peaceful, beautiful and comfortable mountain retreat. Come for outdoor adventures, time on the nearby lakes or just to unwind and soak in the scenery. One of very few mountainside listings with a hot tub, A/C and views!

Northwoods Ski in/Ski Out Home

Northwoods Haven is a stylish and spacious 4-bedroom, 3-bath home, nestled in the heart of Sugarloaf Mountain. Located right on Mountain, Ski in/Ski Out, it’s perfect for year-round adventures at the Loaf. Enjoy cathedral ceilings on the main floor and an additional lower-level space offering plenty of room and fun for everyone. This home provides a warm, inviting setting for family and friends to gather after a day on the slopes or exploring the Western Mountains of Maine

Snowdrop Trailside Condo

Come enjoy the convenience of our all four seasonal Snowflower Trailside Condo located at Sugarloaf Mountain Resort. Mountain views from the living room and a cozy window seat! Biking, hiking and golf all located right out your front door step. Your family will be close to everything. Our 3 bedroom, 3 full bath condo is pet friendly; the perfect location to rest and relax with the comforts of being central to some of the best four season activities this area has to offer.

First Tracks at Sugarloaf

Welcome to First Tracks! Located right on mountain bike trails and less than a three minute walk to Sugarloaf Village. With epic hiking, waterfall swims, disc golf, zip lining and mountain biking right out the back door we've got your vacation covered. Plenty of room to spread out in the condo with a game room downstairs and a hot tub to soothe your tired muscles after a day of play. Sugarloaf in the summer is magical. Let us know if you need any recommendations!

Mountain Biking, Hiking & Golf/Sugarloaf condo A/C

Unwind in the comfort of air conditioning after a day of adventure. The condo features a fully equipped kitchen, modern living area, and access to an indoor pool and tennis courts. Enjoy convenient amenities, including Wi-Fi, parking, and in-house washer and dryer. Whether you’re seeking thrilling outdoor activities or a peaceful mountain escape, our condo is the ideal base for your next vacation. Book now and experience the best of mountain living!