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Search results; Over 1,000 homes in Chesapeake

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Top guest favourite
Guest house in Chesapeake
Beautiful and Chic Studio Apartment
1 bedroom, 1 bed, 1 private bathroom
29 Sept – 4 Oct
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4.98 out of 5 average rating, 263 reviews
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Guest favourite
Guest suite in Chesapeake
Sweet Suite!
1 bedroom, 2 beds, 1.5 bathrooms
11–16 Oct
4.94 out of 5 average rating, 685 reviews
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Top guest favourite
Home in Chesapeake
Quiet 3/2 beautiful Chesapeake
3 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.94 out of 5 average rating, 69 reviews
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Top guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
1 bedroom, 1 bed, 1 bathroom
29 Sept – 4 Oct
4.98 out of 5 average rating, 125 reviews
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Top guest favourite
Guest suite in Chesapeake
Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
4 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 396 reviews
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Superhost
Place to stay in Chesapeake
Private, Spacious Studio Apartment, Bathroom
2 beds, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 240 reviews
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Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Nov
4.9 out of 5 average rating, 196 reviews
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Guest favourite
Room in Chesapeake
Green room
1 queen bed, 2 bathrooms
5–10 Oct
4.8 out of 5 average rating, 71 reviews
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Guest favourite
Home in Chesapeake
Comfy House! The Perfect Getaway
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Sept
4.9 out of 5 average rating, 94 reviews
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Guest house in Chesapeake
Cozy country studio apartment
2 beds, 1 bathroom
20–25 Sept
4.79 out of 5 average rating, 42 reviews
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Top guest favourite
Boat in Portsmouth
Cozy Sailboat Stay in Olde Towne Portsmouth
1 bedroom, 2 beds, WC
29 Sept – 4 Oct
4.96 out of 5 average rating, 24 reviews
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Guest favourite
Apartment in Chesapeake
Entire apartment in Chesapeake, Virginia
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 14 reviews
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Guest favourite
Home in Chesapeake
Simply Amazing in Chesapeake
3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 42 reviews
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Top guest favourite
Guest house in Chesapeake
Western Branch Loft Suite
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.91 out of 5 average rating, 140 reviews
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Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.86 out of 5 average rating, 251 reviews
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Home in Portsmouth
Cozy Historic Home Near Downtown Ferry
2 bedrooms, 2 beds, 1.5 bathrooms
3–8 Oct
4.9 out of 5 average rating, 10 reviews
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Superhost
Room in Chesapeake
Private Entrance, Spacious Master Bedroom Suite
2 beds, 1 bathroom
27 Sept – 2 Oct
4.86 out of 5 average rating, 132 reviews
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Guest favourite
Home in Chesapeake
Cowbell Cottage
3 bedrooms, 7 beds, 1 bathroom
24–29 Sept
4.85 out of 5 average rating, 39 reviews
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Guest favourite
Tiny home in Chesapeake
Tiny house spooky themed sept and Oct Great bridge
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 93 reviews