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Search results; Over 1,000 homes in Port Haywood

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Top guest favourite
Cottage in Port Haywood
Modern Beachfront Cottage with Endless Bay Views
2 bedrooms, 5 beds, 1 private bathroom
6–11 Oct
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4.94 out of 5 average rating, 199 reviews
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Home in Port Haywood
Brighton Winter House - Restored Historic Home
4 bedrooms, 5 beds, 1.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 13 reviews
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Tiny home in Port Haywood
The Tulgey Wood
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 30 reviews
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Top guest favourite
Cottage in Chesapeake
The Cottage @ Captain Genes - Secluded Waterfront
3 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 163 reviews
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Tiny home in Diggs
Stargazer Tiny Cabin
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 235 reviews
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Home in Port Haywood
Relax & Heal Cottage Near Ocean & Forest Retreat
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 69 reviews
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Home in Cobbs Creek
Blue Heron WaterSide
4 bedrooms, 8 beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 176 reviews
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Home in Mathews County
Driftwood Cove Cottage
3 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Onemo
The Harbor House - Waterfront with private pier!
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 80 reviews
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Cottage in Onemo
3 BR Bay Home w Private Dock & all the Amenities
3 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 62 reviews
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Home in Bavon
Your Private Beachfront Retreat - Selah on the Bay
3 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 8 reviews
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Home in Port Haywood
East River/Mobjack Bay Mathews
3 bedrooms, 4 beds, 3 bathrooms
24–29 Nov
4.97 out of 5 average rating, 32 reviews
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Home in New Point
Wilton’s Watch now with 4 BR & 2 Full Bath
4 bedrooms, 5 beds, 2 bathrooms
10–15 Oct
4.96 out of 5 average rating, 98 reviews
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Home in North
Cozy Cottage on The North River
2 bedrooms, 5 beds, 1 bathroom
29 Sept – 4 Oct
4.96 out of 5 average rating, 96 reviews
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Guest favourite
Home in Onemo
Spacious waterfront home, private dock
5 bedrooms, 8 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Home in Gwynn
‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 103 reviews
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Top guest favourite
Home in Mathews
Garden Cottage in Downtown Mathews
1 bedroom, 1 king bed, 1 bathroom
19–24 Oct
4.99 out of 5 average rating, 137 reviews
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Home in Grimstead
Gwynns Island Waterfront Getaway
3 bedrooms, 4 beds, 1 bathroom
16–21 Sept
4.89 out of 5 average rating, 367 reviews
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Guest favourite
Loft in Bohannon
Rooftop Chesapeake Bay Views! Waterfront Retreat
1 king bed, 1 bathroom
29 Sept – 4 Oct
5.0 out of 5 average rating, 7 reviews