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Search results; Over 1,000 homes in Chesapeake

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Top guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
1 bedroom, 1 bed, 1 private bathroom
11–16 Sept
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4.98 out of 5 average rating, 124 reviews
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Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
4.85 out of 5 average rating, 248 reviews
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Top guest favourite
Home in Chesapeake
Cook's Country Escape - Cozy Retreat
3 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.96 out of 5 average rating, 143 reviews
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Top guest favourite
Home in Chesapeake
Quiet 3/2 beautiful Chesapeake
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 65 reviews
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Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.9 out of 5 average rating, 193 reviews
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Guest favourite
Guest suite in Chesapeake
Sweet Suite!
1 bedroom, 2 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 679 reviews
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Guest favourite
Townhouse in Chesapeake
Waterfront Oasis: Fishing Pier, Pool, Beach Access
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 11 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
4.91 out of 5 average rating, 90 reviews
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Top guest favourite
Guest house in Chesapeake
Country Escape - Next DOOR - Hidden Gem
1 bedroom, 4 beds, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 87 reviews
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Guest favourite
Room in Chesapeake
Green room
1 queen bed, 2 bathrooms
7–12 Sept
4.8 out of 5 average rating, 69 reviews
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Guest favourite
Home in Chesapeake
Spacious, 2 Master Suites, sleeps 6-8, 2.5 baths
2 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Chesapeake
Simply Amazing in Chesapeake
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 40 reviews
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Superhost
Place to stay in Chesapeake
Private, Spacious Studio Apartment, Bathroom
2 beds, 1 bathroom
12–17 Sept
4.9 out of 5 average rating, 235 reviews
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Superhost
Home in Norfolk
Modern Comfort Minutes from Waterside & Downtown
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Sept
4.77 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Norfolk
Blessed and peaceful home
4 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 39 reviews
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Home in Chesapeake
Spacious & Stylish in Greenbrier near Hospital
3 bedrooms, 3 beds, 2.5 bathrooms
22–29 Nov
New place to stay
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Guest favourite
Home in Portsmouth
Wooded Wonderland Miniature Golf Hot tub Pool
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 173 reviews
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Guest favourite
Home in Portsmouth
Condo Near Portsmouth Naval on Webster Avenue
3 bedrooms, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 30 reviews
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Guest favourite
Home in Chesapeake
Oasis at the Creek| Park, Family & Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.9 out of 5 average rating, 69 reviews