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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
20–25 Sept
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4.97 out of 5 average rating, 394 reviews
Top guest favourite
Home in Chesapeake
Quiet 3/2 beautiful Chesapeake
3 bedrooms, 4 beds
9–14 Nov
4.94 out of 5 average rating, 69 reviews
Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms, 3 beds
30 Sept – 5 Oct
4.86 out of 5 average rating, 250 reviews
Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
3 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 195 reviews
Top guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
1 bedroom, 1 bed
22–27 Sept
4.98 out of 5 average rating, 125 reviews
Guest favourite
Guest suite in Chesapeake
Sweet Suite!
1 bedroom, 2 beds
11–16 Oct
4.94 out of 5 average rating, 683 reviews
Guest favourite
Home in Chesapeake
Cowbell Cottage
3 bedrooms, 7 beds
24–29 Sept
4.85 out of 5 average rating, 39 reviews
Guest favourite
Room in Chesapeake
Green room
1 queen bed
18–23 Sept
4.8 out of 5 average rating, 71 reviews
Guest favourite
Home in Chesapeake
Simply Amazing in Chesapeake
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 41 reviews
Superhost
Place to stay in Chesapeake
Private, Spacious Studio Apartment, Bathroom
2 beds
16–21 Sept
4.9 out of 5 average rating, 238 reviews
Superhost
Townhouse in Chesapeake
Waterfront Oasis with Fenced Yard
3 bedrooms, 4 beds
5–10 Oct
4.83 out of 5 average rating, 313 reviews
Guest favourite
Home in Chesapeake
2 Master Suites, Sleeps 6-8, King bed, 2.5 baths
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 105 reviews
Superhost
Home in Portsmouth
Wooded Wonderland Miniature Golf Hot tub Pool
4 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 175 reviews
Superhost
Home in Norfolk
Waterfront Home Near VA Beach | Sleeps 16+ | 5BR
5 bedrooms, 11 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chesapeake
The Manor- Extended Stays
4 bedrooms, 5 beds
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Chesapeake
Comfy House! The Perfect Getaway
4 bedrooms, 4 queen beds
20–25 Sept
4.9 out of 5 average rating, 92 reviews
Superhost
Home in Norfolk
Modern Comfort Minutes from Waterside & Downtown
3 bedrooms, 4 beds
20–25 Sept
4.75 out of 5 average rating, 32 reviews
Home in Portsmouth
Yvettes Place 3 Bdrms 2 Bths Mins to Rivers Casino
3 bedrooms, 3 beds
24–29 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chesapeake
Oasis at the Creek| Park, Family & Pet Friendly
3 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 72 reviews