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Search results; Over 1,000 homes in Chesapeake

Top guest favourite
Guest suite in Chesapeake
Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Studio, 4 beds, 1 private bathroom
16–21 Sept
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4.97 out of 5 average rating, 392 reviews
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, 141 reviews
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, 675 reviews
Top guest favourite
Guest house in Chesapeake
Country Escape - Next DOOR - Hidden Gem
1 bedroom, 4 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 86 reviews
Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 246 reviews
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, 64 reviews
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, 192 reviews
Top guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 122 reviews
Superhost
Place to stay in Chesapeake
Private, Spacious Studio Apartment, Bathroom
2 beds, 1 bathroom
29 Aug – 3 Sept
4.9 out of 5 average rating, 234 reviews
Superhost
Townhouse in Chesapeake
Waterfront Oasis with Fenced Yard
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.83 out of 5 average rating, 310 reviews
Home in Portsmouth
Tidewater Treasurer
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
New place to stay
Guest favourite
Home in Chesapeake
Comfy House! The Perfect Getaway
4 bedrooms, 4 queen beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 88 reviews
Guest favourite
Home in Chesapeake
Spacious, 2 Master Suites, sleeps 6-8, 2.5 baths
2 bedrooms, 3 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Chesapeake
Prime Location | Spacious 4BR + Chef's Kitchen
4 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 36 reviews
Guest favourite
Apartment in Chesapeake
Entire apartment in Chesapeake, Virginia
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Room in Norfolk
The Velvet Anchor | Meridian Room: Moody & Soulful
1 double bed, No bathroom
7–12 Sept
5.0 out of 5 average rating, 12 reviews
Hotel in Norfolk
Peaceful Lodging | Beach. BBQ Area. Ocean Views
1 bedroom, 2 double beds, 1 bathroom
23–28 Aug
New place to stay
Townhouse in Portsmouth
Coming Soon! The Emerald Wager!
No bathroom
12–17 Sept
New place to stay
Tiny home in Portsmouth
Backyard Cozy Tiny Home
1 bedroom, 1 sofa bed, 1 bathroom
23–28 Aug
New place to stay