Holiday rentals near Timberline Chairlift
We found 490 holiday rentals — enter your dates for availability
If you are looking to stay near Timberline Chairlift, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Timberline Chairlift
Showing deals for:17 Oct - 24 Oct
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 AU$7,921
AU$7,921
AU$1,132 per night
includes taxes & fees
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 AU$3,464
AU$3,464
AU$495 per night
includes taxes & fees
Image gallery for On Mountain Home, Spectacular Mountain Views, Ski to the Door
1010 out of 10 rating
Exceptional
(68 reviews)
On Mountain Home, Spectacular Mountain Views, Ski to the Door
Carrabassett Valley, ME
8% off
Price is AU$4,246
AU$4,246
AU$607 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 AU$2,028
AU$2,028
AU$290 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 AU$4,388
AU$4,388
AU$627 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 AU$3,482
AU$3,482
AU$497 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 AU$10,196
AU$10,196
AU$1,457 per night
includes taxes & fees
Image gallery for Peaceful, Cozy Cabin Getaway - 4 Season Cabin
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Peaceful, Cozy Cabin Getaway - 4 Season Cabin
Strong, ME
7% off
Price is AU$2,077
AU$2,077
AU$297 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 AU$1,152
AU$1,152
AU$165 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 AU$2,470
AU$2,470
AU$353 per night
includes taxes & fees
Image gallery for Cozy Cabin with Rec Trail and Lake Access!
1010 out of 10 rating
Exceptional
(43 reviews)
Cozy Cabin with Rec Trail and Lake Access!
Rangeley, ME
8% off
Price is AU$2,893
AU$2,893
AU$413 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 AU$5,030
AU$5,030
AU$719 per night
includes taxes & fees
Image gallery for Comfortable mountainside living w/ large outdoor patio, super close to golfing
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Comfortable mountainside living w/ large outdoor patio, super close to golfing
Carrabassett Valley, ME
8% off
Price is AU$5,608
AU$5,608
AU$801 per night
includes taxes & fees
Image gallery for Four season cabin near carrabassett river 5 min. from Sugarloaf mountain.
1010 out of 10 rating
Exceptional
(41 reviews)
Four season cabin near carrabassett river 5 min. from Sugarloaf mountain.
Carrabassett Valley, ME
13% off
Price is AU$1,694
AU$1,694
AU$242 per night
includes taxes & fees
Image gallery for Rangeley Lakefront Cabin. Close to Town. Boat Dock on Property.
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Rangeley Lakefront Cabin. Close to Town. Boat Dock on Property.
Rangeley, ME
16% off
Price is AU$2,927
AU$2,927
AU$418 per night
includes taxes & fees
Image gallery for Riverfront mountain retreat
1010 out of 10 rating
Exceptional
(23 reviews)
Riverfront mountain retreat
Carrabassett Valley, ME
17% off
Price is AU$2,282
AU$2,282
AU$326 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 AU$12,006
AU$12,006
AU$1,715 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
9% off
Price is AU$4,009
AU$4,009
AU$573 per night
includes taxes & fees
Image gallery for Close to Everything, Cozy Cottage for up to 6, Cleanest in Rangeley!
1010 out of 10 rating
Exceptional
(13 reviews)
Close to Everything, Cozy Cottage for up to 6, Cleanest in Rangeley!
Rangeley, ME
8% off
Price is AU$3,110
AU$3,110
AU$444 per night
includes taxes & fees
Image gallery for Sugarloaf Mt. - indoor pool, adjacent to bike trails, on the mountain
1010 out of 10 rating
Exceptional
(69 reviews)
Sugarloaf Mt. - indoor pool, adjacent to bike trails, on the mountain
Carrabassett Valley, ME
8% off
Price is AU$3,152
AU$3,152
AU$450 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 AU$9,610
AU$9,610
AU$1,373 per night
includes taxes & fees
Image gallery for Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
9.49.4 out of 10 rating
Exceptional
(126 reviews)
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Strong, ME
13% off
Price is AU$1,641
AU$1,641
AU$234 per night
includes taxes & fees
Image gallery for Head straight onto the bike trails from your driveway - no car needed!
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Head straight onto the bike trails from your driveway - no car needed!
Carrabassett Valley, ME
8% off
Price is AU$2,375
AU$2,375
AU$339 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 AU$4,927
AU$4,927
AU$704 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Timberline Chairlift
Showing deals for: 13 Oct - 16 Oct
Your Adventure! 360° Mountaintop Views / Off-Grid Retreat on 300 Acres
Sleeps 8 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is AU$2,898
AU$2,898
for 3 nights, 1 home
AU$966 per night
includes taxes & fees
Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
94 reviews(94 reviews)
The current price is AU$694
AU$694
for 3 nights, 1 cabin
AU$231 per night
includes taxes & fees
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
75 reviews(75 reviews)
The current price is AU$827
AU$827
for 3 nights, 1 cottage
AU$276 per night
includes taxes & fees
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
126 reviews(126 reviews)
The current price is AU$831
AU$831
for 3 nights, 1 cottage
AU$277 per night
includes taxes & fees
Private three season cabin nestled in woods on shore of pristine Maine lake
Sleeps 5 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
115 reviews(115 reviews)
The current price is AU$749
AU$749
for 3 nights, 1 cabin
AU$250 per night
includes taxes & fees
Sugarloaf camp - ski/ outdoors rustic retreat
Sleeps 8 · 3 bedrooms · 0+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
The current price is AU$549
AU$549
for 3 nights, 1 cabin
AU$183 per night
includes taxes & fees
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