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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
14–19 Sept
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4.97 out of 5 average rating, 111 reviews
Top guest favourite
Home in Chesapeake
Quiet 3/2 beautiful Chesapeake
3 bedrooms, 4 beds
13–18 Sept
4.93 out of 5 average rating, 60 reviews
Guest favourite
Home in Chesapeake
Comfy House! The Perfect Getaway
4 bedrooms, 4 queen beds
2–7 Aug
4.92 out of 5 average rating, 84 reviews
Top guest favourite
Flat in Chesapeake
Blissful Nook @ Washington
1 bedroom, 1 bed
27 Jul – 1 Aug
4.98 out of 5 average rating, 120 reviews
Townhouse in Chesapeake
The Cove House
4 bedrooms, 4 beds
8–13 Sept
Top guest favourite
Home in Chesapeake
Cook's Country Escape - Cozy Retreat
3 bedrooms, 4 beds
8–13 Aug
4.96 out of 5 average rating, 138 reviews
Top guest favourite
Guest house in Chesapeake
Country Escape - Next DOOR - Hidden Gem
1 bedroom, 4 beds
16–21 Aug
4.99 out of 5 average rating, 81 reviews
Guest favourite
Townhouse in Chesapeake
Family friendly townhouse
3 bedrooms, 4 beds
9–14 Aug
4.9 out of 5 average rating, 186 reviews
Superhost
Home in Norfolk
NEW Cottage Style Family Getaway - Near DT Norfolk
4 bedrooms, 4 beds
30 Jul – 4 Aug
New place to stay
Guest favourite
Home in Chesapeake
Simply Amazing in Chesapeake
3 bedrooms, 4 beds
31 Aug – 5 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Portsmouth
Hidden Gem.4/bedroom cozy home fenced in yard
4 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 104 reviews
Guest favourite
Home in Chesapeake
Cowbell Cottage
3 bedrooms, 7 beds
19–24 Aug
4.89 out of 5 average rating, 35 reviews
Guest favourite
Flat in Portsmouth
Private Boutique Apt •W/D• Near Casino & Downtown
2 bedrooms, 2 beds
30 Aug – 4 Sept
4.92 out of 5 average rating, 24 reviews
Guest favourite
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 bedrooms, 3 beds
30 Sept – 5 Oct
4.85 out of 5 average rating, 241 reviews
Top guest favourite
Guest suite in Chesapeake
Sweet Suite!
1 bedroom, 2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 664 reviews
Superhost
Place to stay in Chesapeake
Private, Spacious Studio Apartment, Bathroom
2 beds
11–16 Aug
4.9 out of 5 average rating, 232 reviews
Guest favourite
Home in Norfolk
Blessed and peaceful home
4 bedrooms, 4 beds
9–14 Aug
4.93 out of 5 average rating, 28 reviews
Superhost
Tiny home in Portsmouth
A Ray of Sunshine
1 bedroom, 2 beds
5–10 Aug
New place to stay
Superhost
Home in Norfolk
10 min to Ocean View Beach: 20% Off Aug
3 bedrooms, 4 beds
23–28 Aug
4.89 out of 5 average rating, 133 reviews