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Search results; Over 1,000 homes in Chesapeake

Top guest favourite
Flat in Chesapeake
Entire Apartment - No Cleaning Fees!
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.97 out of 5 average rating, 109 reviews
Top guest favourite
Home in Chesapeake
Quiet 3/2 beautiful Chesapeake
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 56 reviews
Guest favourite
Home in Chesapeake
Comfy House! The Perfect Getaway
4 bedrooms, 4 queen beds, 2 bathrooms
12–17 Jul
4.91 out of 5 average rating, 81 reviews
Superhost
Townhouse in Chesapeake
Waterfront Oasis: Fishing Pier, Pool, Beach Access
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.85 out of 5 average rating, 238 reviews
Top guest favourite
Home in Chesapeake
Cook's Country Escape - Cozy Retreat
3 bedrooms, 4 beds, 1 bathroom
11–16 Jul
4.96 out of 5 average rating, 136 reviews
Guest favourite
Home in Chesapeake
Cowbell Cottage
3 bedrooms, 7 beds, 1 bathroom
14–19 Aug
4.88 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Chesapeake
Entire apartment in Chesapeake, Virginia
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Jul
4.9 out of 5 average rating, 183 reviews
Superhost
Townhouse in Chesapeake
Waterfront Oasis with Fenced Yard
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
4.83 out of 5 average rating, 301 reviews
Superhost
Home in Chesapeake
Premium Comfort Home
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Aug
4.61 out of 5 average rating, 18 reviews
Superhost
Home in Portsmouth
Cozy Modern Retreat, Peaceful Stay Near Everything
4 bedrooms, 6 beds, 3.5 bathrooms
25–30 Jul
4.9 out of 5 average rating, 10 reviews
Guest favourite
Room in Virginia Beach
Sunny room B
1 queen bed, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 135 reviews
Place to stay in Chesapeake
Cozy Room in Chesapeake 1
1 bedroom, 1 king bed, 1.5 bathrooms
5–10 Jul
4.68 out of 5 average rating, 28 reviews
Guest favourite
Home in Chesapeake
2 Master Suites, Sleeps 6-8, King bed, 2.5 baths
2 bedrooms, 3 beds, 2.5 bathrooms
12–17 Jul
4.96 out of 5 average rating, 98 reviews
Guest favourite
Home in Chesapeake
Simply Amazing in Chesapeake
3 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Guest suite in Chesapeake
Beautiful Two Bedroom King Bed Guest House
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 181 reviews
Guest favourite
Townhouse in Chesapeake
Best Temporary Rental in Chesapeake
2 bedrooms, 2 beds, 2.5 bathrooms
10–15 Aug
4.85 out of 5 average rating, 60 reviews
Top guest favourite
Guest house in Chesapeake
Country Escape - Next DOOR - Hidden Gem
1 bedroom, 4 beds, 1 bathroom
18–23 Jul
4.99 out of 5 average rating, 80 reviews