Chalet vacation rentals in Somerset County

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Top-rated chalet rentals in Somerset County

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Guest favorite

Chalet in Franklin County

4.89 out of 5 average rating, 81 reviews

Saddleback Chalet - Ski-in Ski-out

Ski in, ski out beautiful condo at on the highest road on Saddleback Mountain Ski Resort. Sun filled, 65” and 40” TV’s, extra playroom w couch. Two bedrooms furnished with one queen-size bed in each, and one bunk room with four twin-sized beds. Nice deck w amazing views of Saddleback Lake and beyond. Great place to utilize Saddleback skin trails. 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.

Guest favorite

Chalet in Greenville

4.92 out of 5 average rating, 49 reviews

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!

Guest favorite

Chalet in Kingfield

4.97 out of 5 average rating, 111 reviews

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.

Guest favorite

Chalet in Carrabassett Valley

5 out of 5 average rating, 34 reviews

Chalet w/hot tub, EV charger

In the morning, ski when you want with no long drive. After having a fun day skiing on the mountain or x-country trails, or snowshoeing, fat tire biking, relax in the hot tub or chill in the great room with views of Sugarloaf Mountain while the kids have a blast in the downstairs game room! This new, contemporary ski lodge is perfect for groups or families and their pets. Fully equipped kitchen. Recharge your EVs every day. Heated mud room and boot dryers ensure that your equipment is ready.

Guest favorite

Chalet in Carrabassett Valley

4.97 out of 5 average rating, 108 reviews

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.

Guest favorite

Chalet in Sandy River

4.97 out of 5 average rating, 110 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

Chalet in Highland

4.97 out of 5 average rating, 74 reviews

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.

Guest favorite

Chalet in Wilton

5 out of 5 average rating, 11 reviews

Idyllic Fall Lakefront Escape•Hot Tub•Walk to Town

Suite Serenity Properties presents Tranquil Waters—an idyllic retreat on the stunning shores of Wilson Lake. This brand-new, contemporary chalet is the ultimate lakeside escape, designed for comfort and year-round adventure. Relax in a luxurious hot tub overlooking the lake, taking in panoramic views. Just a short drive from renowned ski mountains, scenic golf courses, snowmobile/ATV trails, a drive-in theater, and UMF, this oasis promises an unforgettable experience in any season!

Superhost

Chalet in Eustis

4.86 out of 5 average rating, 123 reviews

The Chalet on the Ridge-a Mtn, lake and ski escape

The 'Chalet on the Ridge' is a chalet style home that offers 4bdrm/3 baths (+sleeping loft) with breathtaking views of the Bigelow Mountain range. It is a great spot to get away from it all to enjoy outdoor adventures, or just kick back for some R&R. The chalet is just 20 mins to Sugarloaf, 45 mins to Saddleback, and mins from the ITS trail access. Four seasons of activities await you-ski, snowmobile, hunt, fish, bike, golf, hike, swim, boat, dine out, stargaze, or sleep in.

Guest favorite

Chalet in Carrabassett Valley

4.88 out of 5 average rating, 104 reviews

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 :)

Guest favorite

Chalet in Carrabassett Valley

4.94 out of 5 average rating, 104 reviews

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!

Guest favorite

Chalet in Abbot

4.92 out of 5 average rating, 61 reviews

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.