Holiday rentals in Sugarloaf Mountain

Apartment in Carrabassett Valley

4.97 out of 5 average rating, 67 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!

4.81 out of 5 average rating, 103 reviews

Cottage in Embden

Gorgeous lakefront, sunsets, kayaks, fire pit

Enjoy breathtaking sunset views from this cozy, quiet waterfront home. Relax and play at our serene lake house, 40 feet from the water. Embden is the 3rd cleanest lake in Maine and our lot is wooded for nice privacy. Fire pit, lounge chairs and hammock at the water's edge. Kayak, paddleboard, swim, yard games, fish or relax! Great golf close by! In the winter warm up by the fire after playing outside (sugarloaf 35 mins) ski, snowmobile, ice fish for salmon! Our driveway accommodates trailers.

Home in Carrabassett Valley

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!

Home in Carrabassett Valley

4.92 out of 5 average rating, 37 reviews

A Perfect Home For Family Summer Vacations!

This expansive and family-oriented home is situated on Sugarloaf, offering 5 bedrooms, 4.5 bathrooms, two spacious living areas, and a generously sized kitchen and dining space. Located on the Winter shuttle route and within close proximity to hiking/biking trails, the Carrabassett River and golf course! Enjoy the gas fireplace after a day on the slopes or a game of ping pong with the family! Nestled in the mountains, this exquisite home presents an ideal setting for your upcoming vacation.

4.94 out of 5 average rating, 62 reviews

Guest suite in Hanover

Mystery Mountain View Near many outdoor activities

Put up your feet at this 900 sqft rental unit with 1 large bedroom, full kitchen, media room, sitting room, full bath, dining area, and dart board. Private entrance, daylight basement in lower level of our home. There is a key code box to obtain access, and guest parking. 15 minutes to Sunday River and Black Mountain and 20 minutes to Mt. Abram ski resorts. Swimming access at Howard Pond. Skiers, riders, hikers, kayakers, and outdoor enthusiasts would love this location anytime of the year.

4.77 out of 5 average rating, 47 reviews

Cabin in Rangeley

Waterfront Cabin on Rangeley Lake!

True Lyons Cabin 1. Two bedroom, plus sleeping loft, right on Rangeley Lake! Comfy beds and new furnishings! Wonderful little wood stove for those cold nights! 150’ beach with large dock right out front! Large fire pit. Gorgeous views all day long and amazing sunsets! Walking distance to the LOON LODGE & FARM HOUSE Downtown Rangeley 1.5miles away. One bedroom has a queen bed and other has two twins. Loft has full bed. Great WiFi! Brand new Air Conditioning system in entire cabin!

4.8 out of 5 average rating, 15 reviews

Home in Skowhegan

Cozy, Comfortable, welcoming With private suite

Keep it simple at this peaceful and centrally located place. This rental property is in walking distance of the historic area of downtown Skowhegan yet secluded enough to enjoy privacy while on your vacation. Local groceries stores, well-known eateries, and small business shops are just minutes away. Close location to lakes, fairgrounds (active depending on time of stay), movie theaters (Drive-in & Spotlight Cinemas), and more. You need quiet time, enjoy the private suite you’ll love it .

5 out of 5 average rating, 40 reviews

Chalet in Newry

R&R Mountain Retreat in Newry

Welcome to R&R! This charming short-term rental offers a perfect getaway in an ideal location only 6 minutes away from Sunday River Ski Resort! Unwind in our cozy camp featuring modern amenities, comfortable furnishings, and a peaceful ambiance. Enjoy entertainment with Smart TV's, WiFi, cornhole, board games, as well as many nearby attractions. This chalet has so much to offer no matter which season you stay! Your ultimate escape awaits at R&R, where rest and rejuvenation are guaranteed.

5 out of 5 average rating, 119 reviews

Home in Belgrade

SkyView Treehouse | Lakefront • Private Hot Tub

A peaceful retreat nestled in the trees along Belgrade Stream, just minutes from Belgrade Lakes Village and Messalonskee Lake. Built by three generations of our family, SkyView Treehouse is more than a stay — it’s a reflection of everything we value: peace, nature, comfort, and meaningful connection. Whether you’re planning a honeymoon, celebrating an anniversary, or surprising your partner with a birthday getaway, we’ve poured our hearts into making this a place where memories are made.

4.99 out of 5 average rating, 94 reviews

Cabin in Eustis

Private lakefront cabin Flagstaff Oasis.

Flagstaff Oasis is the private, lakefront cabin you have been looking for. Enjoy the endless sunsets from your private dock and outdoor firepit. The cabin sits in a quiet neighborhood, 10 minutes from Sugarloaf for skiers with miles of dirt roads and hiking trails. The lake is perfect for swimming, canoeing and kayaking. Enjoy the all new appliances and fully stocked kitchen and outdoor grill. ATV trails are within a mile and fishing is outstanding in the area. No Jet Skis on Lake!

Flat in Carrabassett Valley

4.67 out of 5 average rating, 6 reviews

Centrally located 1 bedroom condo on mountain!

This one bedroom condo boasts a prime location at the heart of Sugarloaf. Situated along the shuttle route, it's only a brief walk from the Snubber Midstation lift. Walk to the Shipyard Brew Haus for a refreshing drink, or access the Sugarloaf Fitness Center located across the street, for an additional fee. The condo itself includes a fully equipped kitchen, a cozy living room with a gas fireplace and pull out couch, a full bathroom, and a washer/dryer for your convenience.