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!

Family · Value · Access

On Mountain Sugarloaf Condo

**Nightly rate now includes Airbnb's 15.5% service fee** Welcome to your cozy, first-floor, pet-friendly condo at Sugartree! Adventure is right outside your door with ski in/out access to the slopes, biking/hiking trails, downhill bike park, world-class golf course, and breathtaking scenery. Central location with on-site fitness center, pool/hot tubs included for a fee (closed summer). Eat, drink, and shop within a short walk or ride. This is the ideal spot for creating new mountain memories!

Value · Location · Hospitality

Snowflower Village Trailside Condo

Come enjoy a Sugarloaf getaway that is convenient for you and your family with our Ski- in/Ski- out Snowflower Court Trailside Condo, located off the Snowbrook trail and Snubber Chairlift. In the winter, enjoy hitting the slopes and a cozying up in the window seat where you can watch the snow falling down! Our 2 bedroom, 2 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.

Family · Location · Checkout

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*

Value · Family · Biking

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!

Family · Location · Biking

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.

Location · Family · Bathroom

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.

Location · Family · Laundry

Best location on the mountain! Park & Walk!

LOCATED ON THE EAST SIDE OF SUGARLOAF, this is truly the best spot on the mountain! Literally just steps away from the ski trails. Truly a ski in and ski out property. First floor features an updated living room area, full size kitchen, open dining/living area with cathedral ceilings, great wood burning wood stove that opens up to a fireplace, mud room ski locker, deck and prime parking pass. This condo should be your # 1 choice if you are looking for convenience, comfort and affordability.

Family · Location · Condition

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!

Value · Family · Amenities

Sugarloaf Ski-In/Ski-Out Condo w/ Pool

Experience ultimate ski-in/ski-out convenience at Snowbrook Village! Steps from the Snubber Trail and chairlift, this condo lets you quickly access Sugarloaf’s slopes! After skiing, unwind in the private recreation center featuring an indoor pool, hot tubs, and a sauna. Enjoy a fully equipped kitchen, cozy fireplace, and dedicated ski storage. The free resort shuttle stops outside for easy access to base village dining. Perfect for winter ski trips or summer mountain biking!

Value · Family · Layout

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!

Location · Family · Checkout

Great Sugarloaf 2-bedroom unit close to everything

Great Sugarloaf location and comfortable two bedroom condo unit with modern kitchen open to living area. One bath with washer and dryer, wifi and TV. Very comfortable and cozy unit with parking and great access to the mountain. Ski in and ski out with a direct connection to the nordic trails, mountain biking and hiking near Burnt Mountain

Value · Location · Pets