Vacation rentals near Skidway Chairlift
We found 481 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Skidway Chairlift, scroll through and discover private vacation rentals to find the perfect one for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, including WiFi and parking. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Skidway Chairlift
Showing deals for:Nov 14 - Nov 21
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 $3,894 total
CA $3,894 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 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 $3,385 total
CA $3,385 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 $3,018 total
CA $3,018 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 $522
CA $522
CA $4,647 total
CA $4,647 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 Log Cabin Near town
1010 out of 10 rating
Exceptional
(9 reviews)
Log Cabin Near town
Carrabassett Valley, ME
10% off
Price is CA $187
CA $187
CA $1,809 total
CA $1,809 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 $3,344 total
CA $3,344 total
includes taxes & fees
Image gallery for Rangeley Lakefront Cabin. Close to Town. Boat Dock on Property.
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Rangeley Lakefront Cabin. Close to Town. Boat Dock on Property.
Rangeley, ME
20% off
Price is CA $237
CA $237
CA $2,220 total
CA $2,220 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 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
10% off
Price is CA $277
CA $277
CA $2,641 total
CA $2,641 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 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 $204
CA $204
CA $1,956 total
CA $1,956 total
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
20% off
Price is CA $263
CA $263
CA $2,867 total
CA $2,867 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 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
10% off
Price is CA $991
CA $991
CA $8,586 total
CA $8,586 total
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
20% off
Price is CA $660
CA $660
CA $5,700 total
CA $5,700 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Skidway 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)
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)
Top rated rentals - Skidway Chairlift
Favorite Sugarloaf Condo
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
This was our third time staying at this property. Highly recommend it based on location, cleanliness, comfort and host communication.
Marta Z.
Stayed Mar 2025
Excellent accommodation and close to the hill.
1010 out of 10
Exceptionalexceptional
59 reviews(59 reviews)
This is a lovely property—well looked after with excellent appliances, comfy furniture and a convenient ski locker. It is a short walk to the hill and the whiffletree lift. We hope to be back again!
Marnie A.
Stayed Mar 2025
Cozy Home Base
1010 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Great location for a ski vacation. A beautiful spot to rest & relax after a day at the slopes! Accommodations exceeded our expectations with a cozy fire, comfy beds, and great views. Thanks Devon for sharing your space!
Ginger C.
Stayed Mar 2023
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