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Over 1,000 places in Chesapeake

Superhost
Guest suite in Chesapeake
Sweet Suite!
2 beds
Oct 1 – 6
$78 per night
Superhost
Apartment in Great Bridge
Blissful Nook @ Washington
1 bed
Oct 1 – 6
$89 per night
Superhost
Room in Chesapeake
Stay with Nivedita
Eco friendly home private bed-bath & Parking
Oct 1 – 6
$33 per night
Apartment in Chesapeake
Entire Apartment - No Cleaning Fees!
1 king bed
Oct 15 – 20
$85 per night
Superhost
Home in Chesapeake
Cook's Country Escape - House nestled in woods
4 beds
Oct 1 – 6
$113 per night, originally $138
Superhost
Room in Chesapeake
Stay with Terisa
Cozy Room in Chesapeake
Oct 1 – 6
$44 per night
Superhost
Place to stay in Chesapeake
Private, Spacious Studio Apartment, Bathroom
4 beds
Oct 1 – 6
$49 per night, originally $69
Superhost
Townhouse in Chesapeake
2BR-1.5 Bath Electric & Vibrant R&R Townhome
3 beds
Oct 1 – 6
$105 per night
Superhost
Guest suite in Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
1 king bed
Oct 9 – 14
$66 per night
Superhost
Apartment in Chesapeake
Warm Luxury unit Central Greenbrier
1 bed
Oct 11 – 16
$86 per night
Superhost
Guesthouse in Chesapeake
Country Escape - Next DOOR - Hidden Gem
4 beds
Oct 2 – 7
$89 per night
Townhouse in Chesapeake
Cancun Daze
4 beds
Oct 1 – 6
$99 per night
Superhost
Guesthouse in Chesapeake
River House Private Studio Apt-Poolside
1 king bed
Oct 1 – 6
$165 per night
Superhost
Guest suite in Chesapeake
Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
4 beds
Oct 1 – 6
$86 per night
Home in Great Bridge
Townhome in Great Bridge Newly Renovated
3 beds
Oct 1 – 6
$188 per night, originally $223
Superhost
Townhouse in Chesapeake
Best Temporary Rental in Chesapeake
2 beds
Oct 11 – 16
$135 per night
Superhost
Townhouse in Chesapeake
Tasha's Townhouse *King, Queen, Twin*
3 beds
Oct 14 – 19
$132 per night
Superhost
Home in Chesapeake
Hidden Gem in Chesapeake, Virginia
3 beds
Nov 4 – 9
$124 per night