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

4.85 out of 5 average rating, 182 reviews

A two-story home is surrounded by trees, with a welcoming front porch and outdoor seating area. The yard features a well-maintained lawn and stone path, ideal for relaxation and enjoying the natural scenery.

Home in Rumford

Sunnyside close to Sunday River/Black Mt A/C

Sunnyside is the perfect getaway for the family, a group of friends, or couples looking for peace and quiet. In the winter, come enjoy easy access to Sunday River, (20 minutes drive) Black Mountain, ( 7 minutes drive) and Mount Abram -30 minute. In the summer swimming (Ellis Pond, Roxbury Pond) for hikers, Whitecap Mountain Preserve. The trail is great for camping and hiking! Fall foliage is a stunning spectacle. Our home is perfect for your next vacation and we're looking forward to sharing it.

Home in Carrabassett Valley

The exterior of a modern condo is showcased against a mountainous backdrop, featuring a deck and surrounded by trees. Snow-capped slopes are visible in the distance, while the structure is set amidst a natural landscape, providing a serene atmosphere.

5 out of 5 average rating, 16 reviews

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!

An inviting living room features a gas fireplace framed by wooden paneling. Two blue armchairs and a gray sofa, adorned with a checkered throw, are arranged around a wooden coffee table. A window seat with comfortable cushions overlooks the snowy exterior, with natural light brightening the space.

4.92 out of 5 average rating, 12 reviews

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.

An aerial view captures the Sugarloaf mountain and surrounding area, showcasing snow-covered slopes and trails. The Snubber Chairlift is visible along with several snow-dusted buildings nestled among evergreen trees, highlighting the winter landscape.

4.97 out of 5 average rating, 31 reviews

Beautiful Ski InSki out 5 Bedroom Condo Townhouse!

This newly listed condo is the perfect spot for your vacation. A tastefully decorated and vibrant condo centrally located on Sugarloaf mountain. A ski in, ski out property with a chairlift right out back. This spacious and well lit condo features a sunny living room, 4 bedrooms, 3.5 bathrooms, and much more. The kitchen is stocked with everything you need to cook your favorite meals. The living room is comfortable and cozy with hardwood floors and a fireplace to enjoy after a day of skiing!.

Home in Carrabassett Valley

A living space features a modern fireplace framed by dark cabinetry. Two patterned armchairs are positioned around a wooden coffee table atop a plush area rug. A staircase leads to an upper level, while a well-equipped kitchen with wood cabinetry is visible in the background.

4.89 out of 5 average rating, 9 reviews

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.

An aerial view captures the snowy slopes of Sugarloaf, showcasing multiple ski runs against a bright blue sky. The Whiffletree chairlift is visible alongside Gondola Village, where a building sits among the landscapes of trees and winter terrain.

5 out of 5 average rating, 16 reviews

Cozy Condo Park & Walk to the Village of Sugarloaf

When you choose to stay at this centrally located condo, your family will enjoy easy access to numerous attractions. Surrounded by stunning mountain views, the property is just steps away from the Whiffletree chairlift. This cozy two-bedroom, two-bathroom condo comfortably accommodates four guests and features a Smart TV, a gas fireplace, and a fully equipped kitchen, perfect for preparing all your ski meals. Additionally, it is within walking distance of everything Sugarloaf has to offer.

A cozy living area features a comfortable sofa and an accent chair beside a stylish table. A propane fireplace is framed by wooden shelves displaying decorative items. A flat-screen TV is positioned on a wooden console, with board games and books available for guest use.

4.96 out of 5 average rating, 104 reviews

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!

The living room features a stone fireplace surrounded by cozy seating arrangements, including a brown couch and two chairs. A television is mounted on the wall beside bookshelves filled with books. A wooden coffee table sits on a patterned rug, with a window dressed in light curtains allowing natural light.

5 out of 5 average rating, 8 reviews

Trailside Ski Retreat

Welcome to your home away from home. This beautifully designed ski in/ski out condo located in the Snowflower association on Sugarloaf Mountain offers the perfect space for families or groups to unwind and enjoy a relaxing getaway while skiing or snowboarding. This spacious 3 bedroom 3 full bathroom condo sleeps 8 comfortably. Whether you're here to relax, explore the mountain or make core memories with loved ones, this condo offers a comfortable space for everyone.

4.96 out of 5 average rating, 323 reviews

An open living area features large windows with expansive mountain views, allowing natural light to fill the space. Comfortable seating is arranged around a dark coffee table. A sliding door leads to an outdoor deck, enhancing the connection between indoor and outdoor environments.

Chalet in Rangeley

Saddleback Ski Lodge - Ski-in-Ski out Condo

Ski in, ski out beautiful townhouse at on the highest road on Saddleback Mountain Ski Resort. Sun filled, 55" and 40" HDTVs with directv, extra playroom w couch and Giant lovesac beanbag. Master bedroom with king bed, bunk room w double and trundle, upstairs queen. Nice deck w amazing lake views and beyond. 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.

4.98 out of 5 average rating, 134 reviews

A peaceful outdoor deck is showcased with two red Adirondack chairs facing a panoramic view of rolling hills and a clear blue sky adorned with clouds. Lush greenery surrounds the area, enhancing the natural setting.

Chalet in Sandy River

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.

A welcoming three-story, wooden townhouse is showcased, featuring a combination of stone and wood siding. The entrance includes two front doors framed by large windows. A wooden staircase leads to the entryway, surrounded by a gravel path and a rock border.

4.97 out of 5 average rating, 62 reviews

6011 Allagash Drive at Sugarloaf

1,200 square foot townhouse on West Mountain. On mountain convenience, with off the beaten path quietness. It is about a 3-4 minute walk to the West Mountain chair, for 'almost' ski-in ski out convenience. The Explorer Shuttle comes right to the development 3 times an hour on weekends, 2 during the week. Top of the line finishes, fireplace, laundry, gourmet kitchen with exceptional cookware. 1 King Bed in master and a Queen bed in each other room.