Chalet vacation rentals in Somerset County

Moosehead Lakefront Cabin|Pets Ok|Dock|Views|WIFI

Bring the whole family and friends to this great place with lots of room for fun. Lodge style log home with 5 suites, each with a full bathroom. Located on Moosehead Lake in Maine. Great Room with floor to ceiling fireplace and amazing lake views. Enjoy the covered deck with another fireplace! Large lawn area for kids to play. Fun game room. 300 feet of private water frontage and dock. 4 season recreational fun. Fast Starlink WIFI. More info on our page, just search for PineTreeStays and save!

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.

Tucked Away Family Chalet

Tucked Away Family Chalet is conveniently located in Carrabassett Valley close to hiking, biking, community pool/playground/tennis courts, Tufulio's restaurant and much more! A great place to enjoy nature, relax, unwind, check out from the hustle and bustle, and spend quality time with the family. Some of the best mountain biking is right out the front door and swimming in the nearby river is not to be missed. In the wintertime, access to the Narrow Gauge ski trail is a short walk away.

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…

Cheerful three bedroom Cabin in Wyman, Maine

Unwind at a peaceful cabin. Located 6 minutes north of Sugarloaf. This private spot is across from the Bigelow Preserve, close by to the Appalachian Trail head, bike trails, and Flagstaff Lake. There are three bedrooms including a master bedroom with queen size bed & TV, second bedroom has full-size bed & TV, and the third has twin size bunk beds. Downstairs is an open concept living area and kitchen. The yard features a fire pit. Cozy up to the woodstove if you wish and enjoy the scenery.

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.

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.

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.