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Search results; 964 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
Top guest favourite
Home in Portland
2BR Cottage · Lake Lookout · Wine Tasting Included
2 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Portland
Sunset Oasis
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Portland
The Blessing House (Sleeps 15+ (ask)
4 bedrooms, 8 beds
13–18 Sept
4.83 out of 5 average rating, 47 reviews
Guest favourite
Home in Portland
Private Wine Country Estate with 550ft Lakefront
3 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Chalet in Brocton
The Sunset Hideaway
2 bedrooms, 8 beds
20–25 Sept
4.93 out of 5 average rating, 250 reviews
Guest favourite
Home in Brocton
VineCliff - Historic Farmhouse in Vineyard Setting
3 bedrooms, 2 queen beds
13–18 Sept
4.9 out of 5 average rating, 58 reviews
Superhost
Cabin in Portland
Hot Tub, Fire Pit, EV, Wine Tasting | Lux Cabins
3 bedrooms, 4 beds
18–25 Oct
4.83 out of 5 average rating, 23 reviews
Top guest favourite
Home in Van Buren Point
The Dalton
3 bedrooms, 4 beds
24–29 Sept
5.0 out of 5 average rating, 45 reviews
Home in Brocton
Brocton Escape: Skiing, Snowtubing, Hiking!
3 bedrooms, 7 beds
20–25 Sept
4.88 out of 5 average rating, 33 reviews
Top guest favourite
Home in Fredonia
Wine Trail Getaway - Hot Tub open until Oct. 28
3 bedrooms, 6 beds
1–6 Jun
4.96 out of 5 average rating, 80 reviews
Guest favourite
Home in Dunkirk
Point Gratiot Lake House | Sleeps 12+| Lake Views
5 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Fredonia
Charming Historic Retreat on Central Ave
2 bedrooms, 2 queen beds
4–9 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Fredonia
Charming townhouse in Fredonia
2 bedrooms, 3 beds
13–18 Sept
4.97 out of 5 average rating, 119 reviews
Top guest favourite
Cabin in Westfield
Portage Ponds HOT TUB near Lake Erie-CHQ-Wineries
5 bedrooms, 9 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 105 reviews
Top guest favourite
Guest house in Fredonia
Bear Lake Lodge
2 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 63 reviews
Guest favourite
Flat in Westfield
Best of Both Worlds
2 bedrooms, 3 beds
13–18 Sept
4.78 out of 5 average rating, 46 reviews
Guest favourite
Home in Fredonia
Family Estate - pool-tennis-hot tub-hoops-games
9 bedrooms, 16 beds
21–26 May
4.87 out of 5 average rating, 30 reviews
Top guest favourite
Home in Dunkirk
Remodeled home near the beach
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 22 reviews