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Search results; 973 homes in Portland

Top guest favourite
Cottage in Portland
Lake-View Cottage for 4 · Wine Tasting Included
1 bedroom, 1 bed, 1 shared bathroom
4–9 Oct
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4.96 out of 5 average rating, 156 reviews
Superhost
Home in Portland
The Blessing House (Sleeps 15+ (ask)
4 bedrooms, 8 beds, 1.5 bathrooms
12–17 Sept
4.83 out of 5 average rating, 47 reviews
Top guest favourite
Home in Portland
2BR Cottage · Lake Lookout · Wine Tasting Included
2 bedrooms, 3 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Portland
Sunset Oasis
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Portland
Private Wine Country Estate with 550ft Lakefront
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Westfield
Pool Table | Spacious | Perfect Location | Patio
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Chalet in Brocton
The Sunset Hideaway
2 bedrooms, 8 beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 250 reviews
Superhost
Cabin in Portland
Hot Tub, Fire Pit, EV, Wine Tasting | Lux Cabins
3 bedrooms, 4 beds, 2 bathrooms
18–25 Oct
4.83 out of 5 average rating, 23 reviews
Top guest favourite
Home in Mayville
Small town happiness
3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Fredonia
Wine Trail Getaway - Hot Tub open until Oct. 28
3 bedrooms, 6 beds, 2 bathrooms
1–6 Jun
4.96 out of 5 average rating, 80 reviews
Top guest favourite
Guest house in Fredonia
Bear Lake Lodge
2 bedrooms, 4 beds, 1 bathroom
10–15 Sept
4.98 out of 5 average rating, 63 reviews
Home in Brocton
Brocton Escape: Skiing, Snowtubing, Hiking!
3 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.88 out of 5 average rating, 33 reviews
Guest favourite
Home in Dunkirk
Point Gratiot Lake House | Sleeps 12+| Lake Views
5 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Home in Westfield
The Pleasant House
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
New place to stay
Top guest favourite
Home in Mayville
3 Bedroom Countryside Log Cottage Near Chautauqua
3 bedrooms, 3 beds, 1 bathroom
10–15 Sept
4.95 out of 5 average rating, 91 reviews
Guest favourite
Home in Cassadaga
Joann’s Joy - Inspired by Family & Togetherness
4 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 12 reviews
Superhost
Cottage in Fredonia
Gorgeous lakefront home 12 min to Dunkirk Harbor
3 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
4.81 out of 5 average rating, 42 reviews
Home in Fredonia
Country Wine Retreat
3 bedrooms, 4 beds, 1 bathroom
7–12 Oct
New place to stay
Home in Mayville
Lake Chautauqua/Lakefront Estate - 154 W Lake Rd
4 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
4.6 out of 5 average rating, 5 reviews