Chalet holiday rentals in Somerset County

5BR chalet only 6 miles to Sugarloaf access road!

Welcome to Mountain Haven where you will enjoy stunning views of Sugarloaf Mountain while relaxing in the living room, on the back deck, or around the fire pit! This beautiful home features 5 spacious bedrooms and 3.5 bathrooms. Snuggle up in front of the cozy gas fireplace, cook in a fully equipped kitchen, play in a large game room complete with a pool table, or soak your cares away in the jet tub. Located in a quiet neighborhood with easy access to town, restaurants, and recreational parks.

Pristine, Peaceful Kingfield Chalet

Just a short 15-20 minute drive from Sugarloaf and 3 minutes from historic downtown Kingfield, this chalet provides a peaceful, private respite after a busy day on the mountain. Our 2BR, 1BA eco-friendly chalet is tucked back from the road, with distant neighbors and fast WiFi. You can be surrounded by nature but only minutes from lovely restaurants, local shops, grocery store, gas station and tons of trails, rivers & lakes for snowshoeing, XC, snowmobiling, hiking, huts, MTB, kayaking & more.

Relaxing Mountainside Getaway!!!

A spectacular 3/4 bedroom ski-in/ski-out condo on Saddleback Mountain with stunning views of Saddleback Lake! Fits 6 people comfortably. One queen bedroom with attached private full bathroom upstairs. Three bedrooms (king, queen and ski room with pull-out couch that can convert to twins or king). Open living area with propane fireplace, smart tv and WiFi. Offers all the comforts of home and has everything you will need to enjoy some relaxing time away from it all. You won’t want to leave…

Beaver Pond Retreat

In this secluded private setting you will find peace and solitude overlooking the enchanted Beaver Pond from the outdoor hot tub. This is a 4-season retreat for skiing, snowmobiling, cross country skiing, hiking and much more. Beaver Pond Retreat offers 4 bedrooms, 2 full baths, screened in porch/game room, outdoor fire pit and full amenities to make this the perfect getaway for your group! You'll have the comforts of home while enjoying all that nature has to offer at our front door.

The Epic Sugarloaf Family Getaway!

Experience Sugarloaf luxury and celebrate special occasions at this iconic mountainside property. This modern and graciously constructed custom home serves as your portal for adventure. Located in Sugarloaf's Village on the Green neighborhood, you are a mere two-minute ride to the base. Enjoy breathtaking mountain views, gourmet meals in a state-of-the-art kitchen, and endless games, activities, and spaces to unwind in this epic retreat! An unforgettable Sugarloaf experience awaits.

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!

Carrabassett Valley Private Chalet!

We're thrilled to welcome you to Pine Haven, your cozy getaway nestled in the heart of Carrabassett Valley. Whether you're here for the powdery slopes, the rugged biking trails, a peaceful day on the water, or the thrill of the hunt, Pine Haven is your perfect basecamp for adventure—or just unwinding in nature. Tucked away on a private lot off of Route 27, Pine Haven offers the peace and quiet of the wilderness with easy access to all the area’s best attractions.

Welcome to our Shackteau! Close to loaf + trail!

Unique ski chalet five minutes from Sugarloaf access road, with snowshoe / XC ski trail from the property that connects to valley trail system. Cozy, all-wood interior with funky bunk bed tower, homey propane stove, and den with bar and large TV. Equally well-suited for families, friends, and responsible mountain enthusiasts! We love our shackteau and know you will, too! We received negative feedback on our last cleaner so we have a new AWESOME cleaner :)

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.

Cottage 1: Lake View

Cottage 1 is a two bedroom, one bath cottage that has a queen size bed in the primary bedroom and a twin over full size bunk bed with a pull out trundle bed in the secondary bedroom. This cottage is perfect for a group of 4. Comes with complementary coffee and sundries. Please refer to the aerial view of the cottages, to see associated cottage numbers. Dogs will not be allowed in this cottage. Please refer to our *policy* page for more information.

Hillside Hideaway - Great Location & Hot Tub

Welcome to our cozy Sugarloaf/Carrabassett Valley home! Sitting in the back of Redington is our private home with a hot tub, firepit & grill! There is ample parking for you & your friends. Hiking/snowshoeing trail is 100 yards into the woods out of the back of the house. Check us out on the gram @hillsidehideaway_2039. About 10 minutes from the base of Sugarloaf mountain. Family friendly, wi-fi, decked out kitchen. Feel at home within minutes!

Piper Pond A-Frame

Beautiful ALL season home in the Maine woods. Trailer access to ATV trails and direct access to Maines Interconnected Trail System for snowmobiles (ITS). Great location on Piper Pond for swimming, fishing and kayaking! Private home with plenty of room for the whole family. 7 beds in 4 bedrooms with two separate office spaces. Easy access to hiking and Moosehead Lake region. House comes with 5 kayaks, one canoe, paddles and life jackets.