
Holiday rentals near Skidway Chairlift
We found 476 holiday rentals — enter your dates for availability
If you'd like to stay close to Skidway Chairlift, scroll through and discover private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Skidway Chairlift
Showing deals for:19 Sept - 26 Sept
Image gallery for New Listing! Cozy Chalet 10-Minute Drive to Sugarloaf, Sleeps 9

1010 out of 10 rating
Exceptional
(13 reviews)
New Listing! Cozy Chalet 10-Minute Drive to Sugarloaf, Sleeps 9
Carrabassett Valley, ME
12% off
Price is NZ$3,782
NZ$3,782
NZ$540 per night
includes taxes & fees
Image gallery for Sugarloaf Carrabassett Valley 4 Bedroom & 2 Bath Home

1010 out of 10 rating
Exceptional
(16 reviews)
Sugarloaf Carrabassett Valley 4 Bedroom & 2 Bath Home
Carrabassett Valley, ME
8% off
Price is NZ$3,801
NZ$3,801
NZ$543 per night
includes taxes & fees
Image gallery for Air conditioned house! Private house and yard close to golf, hiking, and biking

9.69.6 out of 10 rating
Exceptional
(5 reviews)
Air conditioned house! Private house and yard close to golf, hiking, and biking
Carrabassett Valley, ME
8% off
Price is NZ$4,781
NZ$4,781
NZ$683 per night
includes taxes & fees
Image gallery for Beautiful Ski In/Out Sugarloaf Condo Close to Great Amenities

1010 out of 10 rating
Exceptional
(32 reviews)
Beautiful Ski In/Out Sugarloaf Condo Close to Great Amenities
Carrabassett Valley, ME
8% off
Price is NZ$5,356
NZ$5,356
NZ$765 per night
includes taxes & fees
Image gallery for Rangeley Getaway

1010 out of 10 rating
Exceptional
(62 reviews)
Rangeley Getaway
Rangeley, ME
8% off
Price is NZ$4,000
NZ$4,000
NZ$571 per night
includes taxes & fees
Image gallery for Saddleback Mountain 3-4 BR condo with sweeping views (near Rangeley)

1010 out of 10 rating
Exceptional
(18 reviews)
Saddleback Mountain 3-4 BR condo with sweeping views (near Rangeley)
Rangeley, ME
10% off
Price is NZ$4,536
NZ$4,536
NZ$648 per night
includes taxes & fees
Image gallery for High-end Ski/Golf retreat hot tub, fireplace, 4 bd rm, game rm.

9.49.4 out of 10 rating
Exceptional
(10 reviews)
High-end Ski/Golf retreat hot tub, fireplace, 4 bd rm, game rm.
Carrabassett Valley, ME
8% off
Price is NZ$10,982
NZ$10,982
NZ$1,569 per night
includes taxes & fees
Image gallery for Just a step outside of the hustle & bustle

1010 out of 10 rating
Exceptional
(19 reviews)
Just a step outside of the hustle & bustle
Phillips, ME
16% off
Price is NZ$1,266
NZ$1,266
NZ$181 per night
includes taxes & fees
Image gallery for Kingfield Farm House

9.29.2 out of 10 rating
Wonderful
(38 reviews)
Kingfield Farm House
Carrabassett Valley, ME
10% off
Price is NZ$2,742
NZ$2,742
NZ$392 per night
includes taxes & fees
Image gallery for SUGARLOAF on mountain - Best Place For The Money!

1010 out of 10 rating
Exceptional
(13 reviews)
SUGARLOAF on mountain - Best Place For The Money!
Carrabassett Valley, ME
8% off
Price is NZ$9,056
NZ$9,056
NZ$1,294 per night
includes taxes & fees
Image gallery for Sugarloaf & Flagstaff Lake Vacation Rental

1010 out of 10 rating
Exceptional
(17 reviews)
Sugarloaf & Flagstaff Lake Vacation Rental
Stratton, ME
8% off
Price is NZ$2,692
NZ$2,692
NZ$385 per night
includes taxes & fees
Image gallery for Cozy Entertainment house on Sugarloaf Village I, Spectacular Views!

1010 out of 10 rating
Exceptional
(17 reviews)
Cozy Entertainment house on Sugarloaf Village I, Spectacular Views!
Carrabassett Valley, ME
8% off
Price is NZ$12,083
NZ$12,083
NZ$1,726 per night
includes taxes & fees
Image gallery for Mountain Haven: A cozy 5-bedroom chalet only 6 miles from Sugarloaf access road!

1010 out of 10 rating
Exceptional
(7 reviews)
Mountain Haven: A cozy 5-bedroom chalet only 6 miles from Sugarloaf access road!
Carrabassett Valley, ME
8% off
Price is NZ$6,639
NZ$6,639
NZ$948 per night
includes taxes & fees
Image gallery for Eustis Village Camp - Snowmobiling, Fishing, Hunting, Skiing Sugarloaf

1010 out of 10 rating
Exceptional
(38 reviews)
Eustis Village Camp - Snowmobiling, Fishing, Hunting, Skiing Sugarloaf
Eustis, ME
8% off
Price is NZ$1,852
NZ$1,852
NZ$265 per night
includes taxes & fees
Image gallery for Four season cabin near carrabasset river 5 min. from Sugarloaf mountain

1010 out of 10 rating
Exceptional
(39 reviews)
Four season cabin near carrabasset river 5 min. from Sugarloaf mountain
Carrabassett Valley, ME
13% off
Price is NZ$1,844
NZ$1,844
NZ$263 per night
includes taxes & fees
Image gallery for Beautiful new Log Home - Sugarloaf

1010 out of 10 rating
Exceptional
(22 reviews)
Beautiful new Log Home - Sugarloaf
Carrabassett Valley, ME
25% off
Price is NZ$2,999
NZ$2,999
NZ$428 per night
includes taxes & fees
Image gallery for Sugarloaf Mountain Condo with Indoor Pool, Shuttle and Direct Trail Access!

9.69.6 out of 10 rating
Exceptional
(12 reviews)
Sugarloaf Mountain Condo with Indoor Pool, Shuttle and Direct Trail Access!
Carrabassett Valley, ME
8% off
Price is NZ$5,466
NZ$5,466
NZ$781 per night
includes taxes & fees
Image gallery for Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt

1010 out of 10 rating
Exceptional
(24 reviews)
Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt
Carrabassett Valley, ME
8% off
Price is NZ$2,823
NZ$2,823
NZ$403 per night
includes taxes & fees
Image gallery for On-Mountain Luxury Sugarloaf Ski Condo for Rent -- Great Location!

1010 out of 10 rating
Exceptional
(12 reviews)
On-Mountain Luxury Sugarloaf Ski Condo for Rent -- Great Location!
Carrabassett Valley, ME
8% off
Price is NZ$10,322
NZ$10,322
NZ$1,475 per night
includes taxes & fees
Image gallery for Log Cabin Near town

1010 out of 10 rating
Exceptional
(9 reviews)
Log Cabin Near town
Carrabassett Valley, ME
7% off
Price is NZ$2,218
NZ$2,218
NZ$317 per night
includes taxes & fees
Image gallery for Cozy~ON LIFT~Studio~Sugarloaf Views~Walk to it All!

9.49.4 out of 10 rating
Exceptional
(91 reviews)
Cozy~ON LIFT~Studio~Sugarloaf Views~Walk to it All!
Carrabassett Valley, ME
8% off
Price is NZ$2,185
NZ$2,185
NZ$312 per night
includes taxes & fees
Image gallery for Sugarloaf Area Cabin, Clean, Surrounded by Fir Trees, Stratton, Outdoor Activity

1010 out of 10 rating
Exceptional
(88 reviews)
Sugarloaf Area Cabin, Clean, Surrounded by Fir Trees, Stratton, Outdoor Activity
Stratton, ME
8% off
Price is NZ$1,889
NZ$1,889
NZ$270 per night
includes taxes & fees
Image gallery for Sugarloaf Mt. - on the mountain, adjacent to bike trails, indoor pool

1010 out of 10 rating
Exceptional
(68 reviews)
Sugarloaf Mt. - on the mountain, adjacent to bike trails, indoor pool
Carrabassett Valley, ME
8% off
Price is NZ$3,240
NZ$3,240
NZ$463 per night
includes taxes & fees
Image gallery for Beautiful Trailside Condo - Ski In Ski Out - Shared Seasonal or Nightly Rental

1010 out of 10 rating
Exceptional
(8 reviews)
Beautiful Trailside Condo - Ski In Ski Out - Shared Seasonal or Nightly Rental
Carrabassett Valley, ME
8% off
Price is NZ$2,493
NZ$2,493
NZ$356 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Skidway Chairlift
Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
92 reviews(92 reviews)
Private three season cabin nestled in woods on shore of pristine Maine lake
Sleeps 5 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
113 reviews(113 reviews)
Large Lake House with Private Beach, Dock, Canoe & Kayak
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
78 reviews(78 reviews)
Sugarloaf camp - ski/ outdoors rustic retreat
Sleeps 8 · 3 bedrooms · 0+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Lake House with Swim Area, Dock, Deck, Canoe, & Paddle Boat - 1BR+, Sleeps 4-6
Sleeps 6 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
71 reviews(71 reviews)
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Sleeps 6 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
124 reviews(124 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value