Vacation rentals near Sugarloaf Mountain

4.98 out of 5 average rating, 130 reviews

Chalet in Kingfield

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.

4.99 out of 5 average rating, 101 reviews

A lone moose is depicted standing on a winding dirt path, surrounded by lush greenery. The background features a dense forest with various trees and foliage, reflecting the natural beauty of the area.

Apartment in Eustis

The Dead River Ranch-16 miles from Sugarloaf

A rustic, cozy lower level apartment that offers plenty of open space for a couples retreat. Enjoy, mornings of provided coffee and the great outdoors! Steps away from Pumpkin Pond to the North Branch of Dead River. Enjoy boating on near-by Flagstaff Lake, fishing, hunting, ATV/snowmobile riding for miles on end! Short walk to Trails End Steak House and Tavern, in Eustis village. Skiing or golfing at Sugarloaf Mountain is less then 25 minutes away. Come kick back in the great North Country!

Train in Carrabassett Valley

4.94 out of 5 average rating, 173 reviews

Train Caboose on Mountain

Sugarloaf Village 1 - on mt ,w free shuttle. featured in "Maine Homes by Downeast" mag "Love Train". This beautifully restored caboose w/3 separate sleeping areas - a master bedroom w full bed - single comfortable bunk and a convertible couch. Fully equipped w many ammenities- Flat Screen tv w chromebox- tiled shower -great bedding/linens- full stove & microwave.-fridge- pots pans & cooking supplies -keurig & trad coffe pot-great deck & 1 1/4 yard w pines . U-Tube video JohannaFowler-x5w

The indoor pool area features a spacious design with large windows allowing natural light to illuminate the space. The pool reflects the surrounding trees through the glass, creating a serene atmosphere. Wooden deck areas are present alongside the pool, providing additional seating options.

4.96 out of 5 average rating, 101 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 one of the few with AC for summer!

4.96 out of 5 average rating, 363 reviews

A cat is perched on a windowsill, gazing outside at the scenic view. The landscape showcases a vibrant display of fall foliage alongside the tranquil Carrabassett River. A small waterfall can be seen flowing, reflecting the clear blue sky above.

Apartment in Kingfield

On The River 2 with Lucy the resident cat

On the River 2 is located in the heart of the historic downtown Kingfield on Main street with river views of the Carrabassett river. Miss Lucy Lu (Lucy) is the cat residents who lives in this special apartment. She is the host and will greet you. She loves people. She is an indoor kitty. There is a restaurant next door, the gallery is downstairs, swimming out the back of the building. Sugarloaf mountain close by. Mountains of possibilities to explore in the western area of Maine.

Chalet in Carrabassett Valley

A view of a bathroom is captured from the doorway, showcasing a window that allows natural light to enter. A laundry basket is placed on the floor, while a modern toilet and a clean vanity are visible. Soft lighting complements the wooden interior.

4.88 out of 5 average rating, 113 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 :)

Chalet in Carrabassett Valley

An open-plan living area features wooden walls and ceilings, with a dining table surrounded by black chairs. A modern kitchen with stainless steel appliances is visible, alongside a comfortable seating area. Large windows allow natural light to fill the space, highlighting the natural surroundings.

4.93 out of 5 average rating, 121 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!

A large window framed by warm fairy lights offers a view of a serene snowy landscape outside, with a flowing river visible and snow-covered trees lining the banks.

4.92 out of 5 average rating, 112 reviews

4 Bed 1 Bath on River: Skiing & Mountain bike!

Quiet get away for the family on the river. Hear the sound of the flowing water right outside the windows. 4 Bedroom, 1 Bath, mudroom, radiant floor heat and propane gas stove, full kitchen, with deck and grill. Only a mile from Sugarloaf mountain and the Outdoor center and 24 miles from Flagstaff Lake. Activities include: cross country skiing, skate skiing, downhill skiing, skating and mountain biking, hiking, fishing and golfing.

4.93 out of 5 average rating, 186 reviews

The camp is nestled among tall trees, set slightly elevated above a clear stream. Large boulders and lush greenery surround the water's edge, offering a serene natural setting. The building features a wooden exterior with a sloped roof, harmonizing with the surrounding landscape.

Cabin in Phillips

Stream-side mountain retreat

This attractively renovated camp in the High Peaks region of western Maine is the perfect place to get away and unplug. Surrounded by conservation land, the camp is airy and bright, with views opening onto woods and stream, and is well screened. Solar panels provide water and electricity. There's limited satellite internet service for emailing and texting, and sometimes phone through wifi, depending on your service provider.

Cabin in Carrabassett Valley

A wooden deck features outdoor seating arrangements and a grill, set against a backdrop of lush greenery. The structure's exterior is clad in shingles with a vibrant blue trim, and large glass doors provide a view of the interior.

4.92 out of 5 average rating, 254 reviews

Private Cabin next to Narrow Gauge Trails & River

Historic Ski camp built in 1957! Located a mile from Sugarloaf access road. View of Sugarloaf! Private trail to the Narrow Gauge Parking lot & Trail system. Biking and Hiking right out the door! Only a 4 minute drive to Super Quad and on the Shuttle route. Located within a mile from Anti~Gravity Center, Outdoor Center, Hugs restaurant, Carrabassett Public Library, Mountain Side Grocery Store & Gas station.

Vacation home in Carrabassett Valley

An outdoor terrace is featured with a wooden picnic table and bench, surrounded by natural stone and gravel. Lush greenery encompasses the area, with trees visible in the background under a partly cloudy sky.

4.88 out of 5 average rating, 109 reviews

The Loaf View - 3 Bed Apt - 10 min from Sugarloaf

Relax, ski, snowshoe, mountain bike, hike or just flake out in our spacious three-bedroom lower-level apartment in Reddington East -- just 10-minutes from the Loaf. 1500 square feet, fully equipped kitchen, comfortable living area great for watching the game, blazing fast internet, and a spectacular view of the mountain. There's plenty of room for your skis, coats, and other items in the secure entryway.

Cabin in Freeman Township

A rustic bathroom features warm wood paneling and a compact layout. A white toilet is positioned next to a simple sink on a wooden countertop. Natural light is provided by an overhead fixture, creating a cozy atmosphere.

4.96 out of 5 average rating, 146 reviews

Trailside Cabin

Come & play in the beautiful mountains of western Maine! Cozy, rustic cabin for two. Enjoy miles of multi use trails right off the front steps! If you decide to venture away from the cabin, Rangeley's Saddleback Mt & Sugarloaf USA are both 35 miles away & the college town of Farmington is just 15 minutes south. Our cell service is terrific, but there's no tv or wifi...come to the woods & unplug!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Sugarloaf Mountain vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Sugarloaf Mountain

Superhost

The living area features a cozy seating arrangement with a sofa adorned in striped throw pillows, complemented by a wooden dining set. A mounted television and fireplace are situated on a wooden wall, with a large window providing access to natural light and outdoor views.

4.78 out of 5 average rating, 32 reviews

*New to Market* 410 Snowflower

AbbyRating, 5 stars1 month ago

Perfect space clean nice and everything we needed , would definitely rent again!

5 out of 5 average rating, 34 reviews

Fun all season home on West Mountain.

MarshallRating, 5 stars2 months ago

Kelly's place was great! Lots of space and a great location.

A cozy nook features a comfortably styled daybed surrounded by an arrangement of decorative pillows in varying patterns. A textured blanket is draped over the side. Below, storage baskets and ski boots are neatly organized, enhancing the functional space.

4.91 out of 5 average rating, 47 reviews

Ski in/ski out

LaurynRating, 5 stars3 months ago

Cute little studio with super easy access to the mountain. Would recommend for a couple but would definitely be tight for a family of 5-6.

5 out of 5 average rating, 44 reviews

A wooden dock extends into a tranquil lake, surrounded by trees and reflecting the cloudy sky above. Flower pots are placed at the edge of the dock, adding a touch of color to the peaceful scenery. The calm water reflects the hues of the sky.

Home in Eustis

Flagstaff Lakeside Cabin Retreat

MichelleRating, 5 stars1 week ago

This was a beautiful and well kept location in Northern Maine. We were staying during the off season, so it was very quiet but that’s what we were looking for. The only thing I wasn’t aware of initially, was that the host was charging for the use of the kayaks that are listed as amenities, the weather didn’t cooperate so we didn’t use anything, but that would have been helpful to have in the description of the home. Other than that it was a great space! It was very spacious and cozy!

4.89 out of 5 average rating, 75 reviews

A circular fire pit, surrounded by stone, is positioned on a snowy surface. Several rustic wooden chairs, designed with vintage skis as armrests, are arranged around the fire pit. Leafless trees create a serene backdrop, with a frozen body of water visible in the distance.

Home in Avon

Sandy River Valley Farm House

BrennahRating, 5 stars2 weeks ago

Beautiful place, would definitely return! the area was private and quiet which was what we were looking for. we enjoyed seeing the cattle and sitting outside by the fire pit. our dog had a great time as well. host communicated well and was flexible.

An open-concept living space showcases a modern kitchen with wooden cabinetry and stainless steel appliances. A spiral staircase ascends to the upper level. Large windows allow natural light to fill the area, revealing a blend of natural materials and contemporary design.

4.97 out of 5 average rating, 39 reviews

Sugarloaf/Carrabassett Valley-Bigelow Bear Den

AbbyRating, 5 stars1 month ago

I cannot say enough about how much we loved this house! The fairy lights inside plus the green outside made it feel magical! So peaceful plus all the amenities you need. And the area was perfect for hiking and exploring. Love love love and will definitely be back!

A view of Sugarloaf Mountain reveals its ski slopes, framed by lush greenery and shaded under a cloudy sky. The image captures chairlifts ascending the mountainside, with the base lodge appearing at the foot of the hill, providing access to nearby ski trails.

4.96 out of 5 average rating, 70 reviews

Ski-in-ski-out-sugarloaf-condo

ChristopherRating, 5 stars1 month ago

Shawn’s place was perfect for our family of 4 and our dog. Directly across the street from the Health and Fitness Center and 60 seconds to the base. Had a great trip for some Spring skiing. Great location and value for the price we paid. Thank you.

Superhost