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Search results; Over 1,000 homes in Highland

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Top guest favourite
Chalet in Highland
Beaver Pond - Secluded Retreat
4 bedrooms, 6 beds, 2 private bathrooms
19–24 Oct
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4.96 out of 5 average rating, 102 reviews
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Cabin in Moscow
Driftwood Lodge
4 bedrooms, 4 beds, 1.5 bathrooms
1–6 Nov
New place to stay
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Top guest favourite
Chalet in Carrabassett Valley
5BR chalet only 6 miles to Sugarloaf access road!
5 bedrooms, 10 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Kingfield
Spacious in town location
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 32 reviews
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Superhost
Chalet in Caratunk
Fantastic 4 Season Cabin across from the Kennebec
3 bedrooms, 4 beds, 1 bathroom
30 Sept – 5 Oct
4.74 out of 5 average rating, 117 reviews
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Cabin in Embden
Maine Cottage | Fall Colors, Hiking & Pond Access
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Superhost
Cabin in Kingfield
Red cabin at Carrabassett town line
2 bedrooms, 1 bed, 1 bathroom
20–25 Sept
4.71 out of 5 average rating, 17 reviews
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Guest favourite
Holiday home in Carrabassett Valley
The Loaf View - 3 Bed Apt - 10 min from Sugarloaf
3 bedrooms, 7 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 130 reviews
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Guest favourite
Home in Kingfield
Carrabassett River Retreat
5 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.92 out of 5 average rating, 12 reviews
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Top guest favourite
Home in West Forks
River House in West Forks trail access ITS 86 & 87
4 bedrooms, 12 beds, 3 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 142 reviews
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Guest favourite
Chalet in Carrabassett Valley
Cozy Chalet, 10-Min Drive to Sugarloaf, Sleeps 9
3 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 78 reviews
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Guest favourite
Cabin in Moscow
Mountain side cabin
4 bedrooms, 6 beds, WC
20–25 Sept
4.89 out of 5 average rating, 45 reviews
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Home in Kingfield
3 acre Farmhouse; Sugarloaf, Wifi and game room
4 bedrooms, 7 beds, 1 bathroom
20–25 Sept
4.78 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Carrabassett Valley
Redington Red House
4 bedrooms, 4 beds, 2.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Cabin in Strong
Lakefront Home w/ Dock | Porter Lake | Sugarloaf
3 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
4.92 out of 5 average rating, 180 reviews
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Cabin in Rangeley
Tumblehome Cabin
2 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
New place to stay
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Top guest favourite
Home in New Portland
Riverway Cottage
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 25 reviews
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Guest favourite
Cabin in Carrabassett Valley
Bubblecuffer Cabin: On shuttle Route w/Hot Tub!
4 bedrooms, 9 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Flat in New Vineyard
Springside Farms Memory Lane upstairs apartment
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 85 reviews