Chesapeake Vacation Rentals - HolidayHomes base64Hash Chesapeake Vacation Rentals - HolidayHomes

Chesapeake Vacation Rentals

Browse 735 available vacation homes and compared across 7 trusted partners

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Top-Rated Vacation rentals in Chesapeake

Book the highest-rated Chesapeake vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Butts Station
House with terrace & barbeque | Perfect for remote work
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Apartment Deep Creek South
King Guest Suite - A TOGAR Vacation Rental
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House Greenbrier East
Vacation home | Nature view | Perfect for remote work
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House Pleasant Grove West
Vacation home with garden, grill & terrace | Nature view | Good for workation
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House South Norfolk
Fully equipped nice house with barbeque
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House Deep Creek North
House with yard, terrace & barbeque
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Condo Indian River
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
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House Western Branch North
House with patio | Good for workation
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House Indian River
Southern Charm Warm and WelcomeEntire home hosted by Annette4 guests
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House Deep Creek North
House | Pets allowed
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House Deep Creek North
Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub
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House Western Branch South
Fully equipped nice vacation home with garden & terrace
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House Greenbrier West
Very Decent 4 bedroom / 2 full bath. Located within the heart of the City.
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House Chesapeake
Fully equipped house with garden & pool | Lake view
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House South Norfolk
Vacation home | Dogs allowed
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Top 15 most Recommended Vacation Rentals in Chesapeake

Discover your ideal Chesapeake vacation rental with real-time comparisons of 735 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Condo Indian River
Condo ∙ 4 guests ∙ 1 bedroom

Children-friendly pleasant condo with pool, hot tub & BBQ

Indian River, Chesapeake, Virginia, United States
This 4-person condo in Indian River features a waterfront view and is ideal for family-friendly getaways.
from $205
per night
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House Western Branch North
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque & patio

Western Branch North, Chesapeake, Virginia, United States
This house rental in Western Branch North accommodates 6 guests and features convenient parking for your stay.
from $246
per night
(14)
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House Deep Creek South
House ∙ 8 guests ∙ 4 bedrooms

House with pool

Deep Creek South, Chesapeake, Virginia, United States
This house rental in Deep Creek South accommodates 8 guests and features a private pool for relaxation and enjoyment.
from $328
per night
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House Indian River
House ∙ 2 guests ∙ 3 bedrooms

Children-friendly pleasant vacation home | Perfect for remote work

Indian River, Chesapeake, Virginia, United States
Cozy house rental in Indian River for 2 featuring a fully equipped kitchen perfect for a relaxing getaway.
from $239
per night
(6)
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Apartment Western Branch North
Apartment ∙ 4 guests ∙ 2 bedrooms

Fully equipped ample rental apartment | Suitable for remote work | Dogs allowed

Western Branch North, Chesapeake, Virginia, United States
This apartment rental in Western Branch North accommodates 4 and features a kitchen for convenient meal preparation.
from $129
per night
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House Great Bridge
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped pleasant house with hot tub

Great Bridge, Chesapeake, Virginia, United States
This house rental in Great Bridge accommodates 4 guests and features a convenient kitchen for all your cooking needs.
from $147
per night
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House Western Branch South
House ∙ 10 guests ∙ 5 bedrooms

Charming house with private pool & patio | Pets are welcome

Western Branch South, Chesapeake, Virginia, United States
Spacious house rental in Western Branch South for 10 guests featuring a private pool and ample parking.
from $726
per night
(1)
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House Greenbrier West
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with terrace & yard | Pet-friendly

Greenbrier West, Chesapeake, Virginia, United States
Charming house rental in Greenbrier West for 8 guests featuring a spacious yard and pet-friendly accommodations.
from $245
per night
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Condo South Norfolk
Condo ∙ 2 guests ∙ 1 bedroom

Condo with 1 bedroom for 2 persons

South Norfolk, Chesapeake, Virginia, United States
This cozy condo in South Norfolk accommodates 2 guests and features convenient parking for residents.
from $63
per night
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