Ski-in/Ski-out vacation rentals in Somerset County

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Top-rated ski-in/ski-out rentals in Somerset County

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Carrabassett Valley

4.96 out of 5 average rating, 56 reviews

2BR, 2BA Sugarloaf Mountain Ski-in Ski-out condo

Second-level Sugarloaf Mountain condo getaway! Master bedroom w/ queen bed; upper level open loft bedroom sleeps up to 4 in 1 twin-sized bunk beds + 2 twins; 2 full baths; gas-fireplace; laundry; granite kitchen countertops; & private balcony. Extremely convenient 1-min walk to Snubber chairlift, 30-sec walk to shuttle stop, & easy trail access to Sugarloaf Outdoor Center. Year-round activities: alpine skiing, x-country skiing, snow shoeing, fat biking, mountain biking, golf, hiking, & more!

Guest favorite

Home in Carrabassett Valley

5 out of 5 average rating, 9 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!

Guest favorite

Chalet in Sandy River

4.98 out of 5 average rating, 108 reviews

Saddleback On-Mountain Condo - Family Friendly!

Welcome to the Last Chair Lodge! This is our family-friendly mountainside retreat on the slopes of Saddleback Mountain Ski Area in Rangeley, ME. Ski -in/Ski-out in winter (natural snow dependent), in summer enjoy a peaceful, beautiful and comfortable mountain retreat. The view is breathtaking in all seasons. Come for outdoor adventures, time on the nearby lakes or just to unwind and soak in the scenery. Yes, we have A/C! We have fast fiber WiFi! HDTV w/several streaming services included.

Guest favorite

Rental unit in Carrabassett Valley

5 out of 5 average rating, 36 reviews

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!

Superhost

Home in Carrabassett Valley

4.94 out of 5 average rating, 16 reviews

Timbers Pow Shack 4bdrm/4.5 bath

Best ski in-ski out at Sugarloaf. On and off slopes just above the Superquad. Main floor -Open concept kitchen/dining/living. 70 inch round table seats 8. Five bar stools at counter. King sized master with en-suite (twin sinks, jacuzzi tub, separate shower) access to patio . Lower level features rec room with full sized pool table, full bath, sliding door to slopes. Upper level features 3 bedrooms and 2 baths , including queen bed, full/twin bunk, and twin bunk bed. SmartTV’s

Superhost

Home in Sandy River

5 out of 5 average rating, 11 reviews

Wulff Haus - Modern Ski Retreat on Saddleback Mtn.

Newly built in 2023, Wulff Haus is a family ski retreat nestled trailside in the ski-in/ski-out Magalloway neighborhood on Saddleback Mountain. Our home features a spacious kitchen/dining area, four bedrooms, two bathrooms, a large mudroom with storage for ski gear, gas fireplace, and a remote work area. Kids (and adults!) will love our bunk bedroom, featuring four bunks. Enjoy all that Rangeley has to offer year-round with lakes, trails, hiking, fishing, skiing and more!

Guest favorite

Rental unit in Carrabassett Valley

5 out of 5 average rating, 17 reviews

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.

Guest favorite

Condo in Carrabassett Valley

4.96 out of 5 average rating, 78 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 AC for summer!

Guest favorite

Guesthouse in Cornville

5 out of 5 average rating, 111 reviews

Quiet Retreat; Barker Pond Farm Cabins, LLC: Pine

Barker Pond Farm Cabins, built in 2010, feature modern amenities including a full bath and kitchen, outfitted with towels, linens and cookware. Each cabin sleeps 4 people, with a queen sized bedroom and a 2 twin sleeping loft, accessed by a ship's ladder. A screened-in porch is the perfect place to sit and listen to our resident loons. We offer two identical cabins for rent, Pine, listed here, and Spruce, which can be found under "Barker Pond Farm Cabins; Spruce"

Guest favorite

Condo in Carrabassett Valley

4.96 out of 5 average rating, 50 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.

Guest favorite

Condo in Carrabassett Valley

4.96 out of 5 average rating, 73 reviews

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, a massage chair and a hot tub to recover after a day of adventure.

Superhost

Home in Carrabassett Valley

4.67 out of 5 average rating, 24 reviews

Condo near wiffletree chairlift!

3 bedrooms 2 bathroom with 7 bed condo ! Can easily fit 10 people (perfect for 2 familly) ! Short walk to Wiffletree chairlift ! Lots of commodity included so you can only bring your food, personal items and outdoor gear. Spend the day skiing and relax when the evening comes. The condo is also near of golf course, the mountain bike trail and more !