Holiday rentals near Timberline Chairlift
We found 492 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:14 Nov - 21 Nov
Image gallery for Mountain Haven: A cozy 5-bedroom chalet only 6 miles from Sugarloaf access road!
1010 out of 10 rating
Exceptional
(9 reviews)
Mountain Haven: A cozy 5-bedroom chalet only 6 miles from Sugarloaf access road!
Carrabassett Valley, ME
8% off
Price is S$6,114
S$6,114
S$873 nightly
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 S$8,912
S$8,912
S$1,273 nightly
Includes taxes & fees
Image gallery for 4 BR Mountain View Adventure on 15 Acres
1010 out of 10 rating
Exceptional
(12 reviews)
4 BR Mountain View Adventure on 15 Acres
Rangeley, ME
7% off
Price is S$3,595
S$3,595
S$514 nightly
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 S$4,718
S$4,718
S$674 nightly
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 S$3,693
S$3,693
S$528 nightly
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 S$1,693
S$1,693
S$242 nightly
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 S$2,279
S$2,279
S$326 nightly
Includes taxes & fees
Image gallery for Rangeley Lakefront Cabin. Close to Town. Boat Dock on Property.
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Rangeley Lakefront Cabin. Close to Town. Boat Dock on Property.
Rangeley, ME
16% off
Price is S$2,050
S$2,050
S$293 nightly
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
8% off
Price is S$3,087
S$3,087
S$441 nightly
Includes taxes & fees
Image gallery for On Mountain Home, Spectacular Mountain Views, Ski to the Door
1010 out of 10 rating
Exceptional
(69 reviews)
On Mountain Home, Spectacular Mountain Views, Ski to the Door
Carrabassett Valley, ME
8% off
Price is S$3,572
S$3,572
S$510 nightly
Includes taxes & fees
Image gallery for Cozy & Peaceful Waterfront Cabin on Porter Lake!
1010 out of 10 rating
Exceptional
(18 reviews)
Cozy & Peaceful Waterfront Cabin on Porter Lake!
New Vineyard, ME
14% off
Price is S$2,671
S$2,671
S$382 nightly
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 S$1,824
S$1,824
S$261 nightly
Includes taxes & fees
Image gallery for Valley Home with Game Room, Walking Distance to Narrow Gauge Trails & Restaurant
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Valley Home with Game Room, Walking Distance to Narrow Gauge Trails & Restaurant
Carrabassett Valley, ME
8% off
Price is S$2,466
S$2,466
S$352 nightly
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 S$4,231
S$4,231
S$604 nightly
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
8% off
Price is S$2,380
S$2,380
S$340 nightly
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
12% off
Price is S$5,717
S$5,717
S$817 nightly
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 S$8,370
S$8,370
S$1,196 nightly
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
9% off
Price is S$3,825
S$3,825
S$546 nightly
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 S$1,921
S$1,921
S$274 nightly
Includes taxes & fees
Image gallery for West Mountain Trailside - ski in/ski out breakaway apartment.
1010 out of 10 rating
Exceptional
(5 reviews)
West Mountain Trailside - ski in/ski out breakaway apartment.
Carrabassett Valley, ME
17% off
Price is S$5,254
S$5,254
S$751 nightly
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
(25 reviews)
Ski In Ski Out Family Friendly Sugarloaf Condo @ Snubber Trail Mid Station on Mt
Carrabassett Valley, ME
8% off
Price is S$2,526
S$2,526
S$361 nightly
Includes taxes & fees
Image gallery for Trailside, four bedroom, sun filled condo, with pool, view of Sugarloaf and AC
9.69.6 out of 10 rating
Exceptional
(89 reviews)
Trailside, four bedroom, sun filled condo, with pool, view of Sugarloaf and AC
Carrabassett Valley, ME
12% off
Price is S$2,550
S$2,550
S$364 nightly
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 S$2,117
S$2,117
S$302 nightly
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 S$4,145
S$4,145
S$592 nightly
Includes taxes & fees
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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
9.49.4 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Your Adventure! 360° Mountaintop Views / Off-Grid Retreat on 300 Acres
Sleeps 8 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 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)
Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
96 reviews(96 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)
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