Vacation rentals in Carrabassett Valley

4.98 out of 5 average rating, 137 reviews

A cozy chalet is situated in a snowy landscape, framed by tall, bare trees. The wooden exterior combines rustic charm with modern design. A covered entrance welcomes guests, leading to a snow-covered pathway surrounded by a serene, wintry environment.

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, 103 reviews

A lower level apartment is visible beneath a red two-story structure. A stone pathway leads to a seating area featuring a round table with four chairs, shaded by a red umbrella. Logs are stacked nearby, and greenery surrounds the property, offering a serene outdoor space.

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

A restored red caboose is surrounded by freshly fallen snow, softly illuminated by warm indoor lighting. Snow-covered trees frame the scene, creating a cozy yet secluded atmosphere. The structure showcases its original features, contrasting with the winter landscape.

4.94 out of 5 average rating, 174 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

Condo in Carrabassett Valley

A cozy living area features a comfortable sofa and an accent chair beside a stylish table. A propane fireplace is framed by wooden shelves displaying decorative items. A flat-screen TV is positioned on a wooden console, with board games and books available for guest use.

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, 367 reviews

A cozy living area is highlighted by an electric fireplace set against a stone wall, providing a warm focal point. Two glasses of red wine sit on a rustic glass table, accompanied by decorative wood coasters and a small plant nearby.

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.

4.99 out of 5 average rating, 104 reviews

A tranquil outdoor space features a wooden pergola with seating and a grill, situated beside a hot tub. The fenced backyard is surrounded by tall trees, and the charming house is accentuated by a beautiful sunset sky.

Cabin in Kingfield

Cozy Cabin with Modern Amenities. Pet Friendly!

Kick back and relax in this beautifully renovated home with amenities you didn't know you were missing. Despite its small stature, every square inch is utilized, boasting 4 beds and 1.5 bathrooms, including a huge shower with multiple shower heads and hurricane force water pressure. Located on a quiet street just minutes from the Kingfield village, steps from the snowmobile trail system, and 20 minutes from Sugarloaf. Designed with dogs in mind, complete with a fenced in backyard.

4.87 out of 5 average rating, 143 reviews

An open concept first floor showcases natural wood elements, with a spiral staircase leading to the loft. A wood stove is positioned near large south-facing windows, allowing natural light to enhance the space. A cozy seating area is complemented by a stack of firewood and greenery.

Cabin in Coplin

Cozy Cabin close to Sugarloaf Mountain

This 1100 square foot cozy cabin in the woods is 8 miles north of Sugarloaf ski resort, 25 minutes north east of Rangeley Lake and 5 minutes from Flagstaff Lake. It is equipped with dimmable recessed lighting, a ceiling fan, a front porch, and back deck. There is a loft with a queen bed in addition to the queen bed in the bedroom. Wifi is available on sight as well as a 55" Roku smart TV. This cabin has had many recent updates primarily on the first floor and loft areas.

Chalet in Carrabassett Valley

A cozy living area features natural wood walls and a wooden floor. Multiple seating options, including chairs and a plush lounge cushion, are arranged around a coffee table. A propane stove stands next to the entrance, and natural light fills the space through large windows.

4.89 out of 5 average rating, 117 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 :)

Cabin in Carrabassett Valley

A rustic ski camp is surrounded by snow-covered trees, with soft illumination coming from a window. The building, featuring natural wood accents and a sloped roof, is partially obscured by snow drifts, creating a serene winter landscape.

4.9 out of 5 average rating, 104 reviews

Sugarloaf Mountain, Slim Melvin House

Classic ski camp originally built in 1960 by Sugarloaf founding father, Walter”Slim” Melvin, and updated in 1998. All pine interior. Carpeted second floor bed rooms. Just 3 miles south of the Sugarloaf Mountain access rd. The camp is a very quiet retreat for family and friends. Dog friendly. Snow shoe out the back door and connect with the trails of the Outdoor center. Tune your skis on the basement work bench. Valley shuttle is available on call.

Chalet in Carrabassett Valley

The charming wooden house features a gabled roof and large windows framed in white. A welcoming front porch is visible, and flower beds with assorted greenery enhance the entrance. An American flag is displayed, complementing the natural surroundings.

4.93 out of 5 average rating, 124 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 serene riverbank is framed by lush green trees and foliage. Clear water reflects the surrounding nature, with smooth stones scattered along the shore. Gentle ripples indicate flowing water, creating a tranquil atmosphere for outdoor activities.

4.92 out of 5 average rating, 113 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.

Cabin in Carrabassett Valley

An outdoor seating area features a circular stone fire pit surrounded by a blue rug. A wicker couch with blue cushions provides comfortable seating, accompanied by a wicker coffee table. French doors lead into the cabin, complementing the rustic wooden exterior.

4.92 out of 5 average rating, 260 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 rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Carrabassett Valley vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Carrabassett Valley

A cozy living area features comfortable leather seating arranged around a wooden coffee table. Large windows allow natural light to fill the space, showcasing a classic area rug on warm wooden flooring. Soft throws are draped over one chair, adding a touch of comfort.

4.87 out of 5 average rating, 15 reviews

Whispering Spruce Lodge | Sugarloaf Mountain House

An open concept living area features a spacious sectional couch, accompanied by a modern gas fireplace. A festive Christmas tree is illuminated in the corner, while a ladder leads to the open loft above. Natural light fills the room through large windows.

5 out of 5 average rating, 11 reviews

Carrabassett Cabin

5 out of 5 average rating, 71 reviews

A serene scene features a person fishing by the river, surrounded by lush greenery and mountain views in the distance. The interior showcases wooden beams and a spacious kitchen with stainless steel appliances, complemented by bar stools along a large island.

Home in Eustis

New Cabin. Mountain, River & Dam Views, Kayaks.

Apartment in Carrabassett Valley

An aerial view showcases a modern penthouse condo nestled among vibrant autumn foliage. The surrounding mountains rise in the background, emphasizing the natural beauty of the area. Nearby buildings and roads are visible, indicating a well-connected location.

4.94 out of 5 average rating, 49 reviews

Summit Haus - Golf & Liftside Penthouse!

5 out of 5 average rating, 52 reviews

A welcoming living area features a comfortable leather couch and a plush armchair, arranged around a wooden coffee table. A flat-screen TV is positioned across from the seating. Light wood paneling and a large window allow natural light to brighten the space.

Apartment in Kingfield

Rustic Elegance

Chalet in Carrabassett Valley

The living room features vaulted wooden ceilings and large windows that provide natural light and views of the outdoors. A cozy seating arrangement with a sofa and armchair faces a stone fireplace, while a decorative lamp and coffee table add to the welcoming ambiance.

5 out of 5 average rating, 18 reviews

5BR chalet only 6 miles to Sugarloaf access road!

A charming two-story home is visible, featuring a unique A-frame design with textured siding. Two bicycles are positioned at the front, indicating accessibility for outdoor activities. Surrounding greenery offers a natural backdrop, enhancing the inviting appeal of the residence.

5 out of 5 average rating, 12 reviews

Riverside home perfect for outdoor enthusiasts!