Vacation rentals near Timberline Chairlift
We found 496 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Timberline Chairlift, scroll through and discover private vacation rentals to find the perfect one for your trip. Whether you're staying in a vacation rental with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. What you'll find is a rental for everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Timberline Chairlift
Showing deals for:Nov 7 - Nov 14
Image gallery for Mountain Haven: A cozy 5-bedroom chalet only 6 miles from Sugarloaf access road!
1010 out of 10 rating
Exceptional
(8 reviews)
Mountain Haven: A cozy 5-bedroom chalet only 6 miles from Sugarloaf access road!
Carrabassett Valley, ME
10% off
Price is CA $743
CA $743
CA $6,569 total
CA $6,569 total
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
10% off
Price is CA $1,026
CA $1,026
CA $9,114 total
CA $9,114 total
includes taxes & fees
Image gallery for 4 BR Mountain View Adventure on 15 Acres
1010 out of 10 rating
Exceptional
(11 reviews)
4 BR Mountain View Adventure on 15 Acres
Rangeley, ME
10% off
Price is CA $386
CA $386
CA $3,845 total
CA $3,845 total
includes taxes & fees
Image gallery for Rangeley Lake Views at The Pine Tree Perch. Close to Town & Saddleback Mountain.
1010 out of 10 rating
Exceptional
(28 reviews)
Rangeley Lake Views at The Pine Tree Perch. Close to Town & Saddleback Mountain.
Rangeley, ME
5% off
Price is CA $327
CA $327
CA $2,969 total
CA $2,969 total
includes taxes & fees
Image gallery for 12 Acre Orchard Cabin Getaway
9.89.8 out of 10 rating
Exceptional
(6 reviews)
12 Acre Orchard Cabin Getaway
New Portland, ME
5% off
Price is CA $622
CA $622
CA $5,503 total
CA $5,503 total
includes taxes & fees
Image gallery for Private Log Home in Rangeley! With marina access.
1010 out of 10 rating
Exceptional
(12 reviews)
Private Log Home in Rangeley! With marina access.
Rangeley, ME
5% off
Price is CA $370
CA $370
CA $3,329 total
CA $3,329 total
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
10% off
Price is CA $557
CA $557
CA $5,117 total
CA $5,117 total
includes taxes & fees
Image gallery for Newly built custom home nestled on the edge of the Bigelow Preserve
1010 out of 10 rating
Exceptional
(5 reviews)
Newly built custom home nestled on the edge of the Bigelow Preserve
Stratton, ME
10% off
Price is CA $681
CA $681
CA $6,129 total
CA $6,129 total
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
10% off
Price is CA $435
CA $435
CA $3,968 total
CA $3,968 total
includes taxes & fees
Image gallery for Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise
1010 out of 10 rating
Exceptional
(23 reviews)
Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise
Rangeley, ME
5% off
Price is CA $372
CA $372
CA $3,432 total
CA $3,432 total
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
10% off
Price is CA $222
CA $222
CA $1,994 total
CA $1,994 total
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
10% off
Price is CA $190
CA $190
CA $1,838 total
CA $1,838 total
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
15% off
Price is CA $263
CA $263
CA $2,443 total
CA $2,443 total
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
10% off
Price is CA $425
CA $425
CA $3,838 total
CA $3,838 total
includes taxes & fees
Image gallery for Close to Everything, Cozy Cottage for up to 6, Cleanest in Rangeley!
1010 out of 10 rating
Exceptional
(14 reviews)
Close to Everything, Cozy Cottage for up to 6, Cleanest in Rangeley!
Rangeley, ME
10% off
Price is CA $358
CA $358
CA $3,290 total
CA $3,290 total
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
10% off
Price is CA $239
CA $239
CA $2,241 total
CA $2,241 total
includes taxes & fees
Image gallery for Valley Home with Game Room, Walking Distance to Narrow Gauge Trails & Restaurant
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Valley Home with Game Room, Walking Distance to Narrow Gauge Trails & Restaurant
Carrabassett Valley, ME
10% off
Price is CA $277
CA $277
CA $2,641 total
CA $2,641 total
includes taxes & fees
Image gallery for On-Mountain Home w/ Best View of Sugarloaf!
1010 out of 10 rating
Exceptional
(44 reviews)
On-Mountain Home w/ Best View of Sugarloaf!
Carrabassett Valley, ME
5% off
Price is CA $845
CA $845
CA $7,957 total
CA $7,957 total
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
10% off
Price is CA $522
CA $522
CA $4,550 total
CA $4,550 total
includes taxes & fees
Image gallery for HOT TUB! Close to Sugarloaf, Hiking, and biking! Outdoor Paradise! Pac-Man!!
1010 out of 10 rating
Exceptional
(62 reviews)
HOT TUB! Close to Sugarloaf, Hiking, and biking! Outdoor Paradise! Pac-Man!!
Carrabassett Valley, ME
5% off
Price is CA $285
CA $285
CA $2,645 total
CA $2,645 total
includes taxes & fees
Image gallery for New Cabin in Eustis.Mtn, River & Dam Views
1010 out of 10 rating
Exceptional
(55 reviews)
New Cabin in Eustis.Mtn, River & Dam Views
Eustis, ME
10% off
Price is CA $283
CA $283
CA $2,550 total
CA $2,550 total
includes taxes & fees
Image gallery for Great spot located in the Valley, just 6 miles south of Sugarloaf!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Great spot located in the Valley, just 6 miles south of Sugarloaf!
Carrabassett Valley, ME
15% off
Price is CA $672
CA $672
CA $6,139 total
CA $6,139 total
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 CA $513
CA $513
CA $4,102 total
CA $4,102 total
includes taxes & fees
Image gallery for Stunning 4bd/2.5b condo, beach access Rangeley Lake, close to town & Saddleback
1010 out of 10 rating
Exceptional
(29 reviews)
Stunning 4bd/2.5b condo, beach access Rangeley Lake, close to town & Saddleback
Rangeley, ME
5% off
Price is CA $457
CA $457
CA $4,320 total
CA $4,320 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Timberline Chairlift
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)
Your Adventure! 360° Mountaintop Views / Off-Grid Retreat on 300 Acres
Sleeps 8 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
96 reviews(96 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
127 reviews(127 reviews)
Sugarloaf camp - ski/ outdoors rustic retreat
Sleeps 8 · 3 bedrooms · 0+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Large Lake House with Private Beach, Dock, Canoe & Kayak
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
Top rated rentals - Timberline Chairlift
Sugarloaf
1010 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Cozy Home Base
1010 out of 10
Exceptionalexceptional
28 reviews(28 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, yards and more
More for lessMore space, more privacy, more amenities — more value