Ski-in/Ski-out vacation rentals in Sugarloaf Mountain

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!

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!

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, Prime Location, Park & Walk!

Your family will enjoy unparalleled convenience when you stay at this centrally located condo on Sugarloaf Mountain. This prime location offers ski-in/ski-out access, with chairlifts visible from your unit. The condo features a queen-sized Murphy bed, built-in bunk beds, full bathroom, living room equipped with a gas fireplace, and a compact kitchen. Additionally, you can easily walk to nearby restaurants and shops. The property is also situated on the shuttle route for added accessibility.

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.

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio

This cozy and comfy ski in/ski out condo is in a desirable location and just a short chairlift ride to the base of Sugarloaf Mountain. Ski or mountain bike directly from the condo! Family friendly. A queen bed settled in an alcove, queen murphy bed and pull out full size sofa bed provide plenty of sleeping space. Convenient indoor access to the pool, hot tubs, and sauna at the Sugarloaf Sports and Fitness Center (additional fees apply). Full kitchen, and one of the few with AC for summer!

Ski In/Ski Out Studio Condo W/ Mountain Views!

This studio condo offers ski-in, ski-out convenience and can accommodate up to three guests. Ideally located, this cozy retreat features one bathroom, a plush queen-sized bed and a single bed, all oriented toward the mountain for breathtaking views. The property is conveniently situated near two ski lifts: the mid-station Snubber lift is just outside the door, while the Sawduster chair lift is a short distance away. Enjoy the unparalleled luxury of skiing directly back to your doorstep.

On-Piste, Ski-in/Ski-out Condo

*NEW LISTING* Book your stay at this ski-in ski-out, cozy studio condo centrally located at Sugarloaf USA. Upon arrival, no need to move your car! You will receive 2 parking passes, be steps from the Snubber Chair lift, settle your belongings in your personalized ski locker and walk a few minutes to the many shops and restaurants in the village. Warm up beside the electric fireplace between runs when you come in for lunch or a cup of coffee. Location, location, location! End unit condo!

Out of Bounds Lounge

Welcome to your perfect ski getaway at our "Out of Bounds Lounge." This hotel-style condo is nestled directly on mountain in Sugarloaf's West Village, perched above the soon to-be Brickyard Hollow Pizza. This condo comfortably sleeps 2 guests with direct access to the SuperQuad lift, unbeatable mountain views, and easy access to Sugarloafs vibrant village (don't miss a burger from the Bag & Kettle!) This Condo offers everything you need for a memorable mountain getaway.

Mountainside at Saddleback - Sunsets! Views!

Welcome to the Last Chair Lodge - our family-friendly mountainside retreat at Saddleback Ski Area in Rangeley, ME. 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. Yes, we have A/C and fast fiber WiFi! HDTV w/streaming services included.

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.

First Tracks at Sugarloaf

Welcome to First Tracks! Our home is located in the Timbers, a great jumping off point for all your adventures. Located right on the ski trail and less than a three minute walk to Sugarloaf Village. Plenty of room to spread out in the condo with a game room downstairs (ping pong tourney anyone?). Two fireplaces, cozy seating, games and a hot tub to recover after a day of adventure.