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Search results; 962 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, 14 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
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
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
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
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
Top guest favourite
Cottage in Fredonia
Rock Cottage Getaway
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 233 reviews
Guest favourite
Home in Fredonia
Family Estate - pool-tennis-hot tub-hoops-games
9 bedrooms, 16 beds, 4.5 bathrooms
21–26 May
4.86 out of 5 average rating, 29 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
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
Home in Fredonia
Country Wine Retreat
3 bedrooms, 4 beds, 1 bathroom
7–12 Oct
New place to stay
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
Top guest favourite
Cabin in Westfield
Portage Ponds HOT TUB near Lake Erie-CHQ-Wineries
5 bedrooms, 9 beds, 3 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 105 reviews
Top guest favourite
Home in Fredonia
Charming townhouse in Fredonia
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 119 reviews