Chesapeake Vacation Rentals

Find quality vacation rentals and city apartments!

Top deals for house rentals in Chesapeake

Find best vacation rental deals in Chesapeake and save up to 63%

e.g. 12/3 - 12/10 (Sat - Sat)

-63%

~~$392~~

$144 per night

House ∙ 4 guests ∙ 2 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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e.g. 12/4 - 12/11 (Sun - Sun)

-40%

~~$258~~

$154 per night

Condo ∙ 2 guests ∙ 1 bedroom

4.0

"Very good" (2 ratings)

Indian River, Chesapeake, Virginia, United States

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e.g. 12/4 - 12/11 (Sun - Sun)

-36%

~~$225~~

$144 per night

Apartment ∙ 3 guests ∙ 1 bedroom

Indian River, Chesapeake, Virginia, United States

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Pet-friendly rentals in Chesapeake

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

$675 per night

House ∙ 11 guests ∙ 4 bedrooms

Greenbrier West, Chesapeake, Virginia, United States

Pet-friendly

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$88 per night

Apartment ∙ 3 guests ∙ 1 bedroom

4.9

Outstanding (51 ratings)

Deep Creek South, Chesapeake, Virginia, United States

Pet-friendly

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$163 per night

House ∙ 6 guests ∙ 3 bedrooms

5.0

Outstanding (2 ratings)

Western Branch North, Chesapeake, Virginia, United States

Pet-friendly

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Accommodation with Internet in Chesapeake

Choose your ideal rental with Internet and WiFi in Chesapeake

$237 per night

House ∙ 8 guests ∙ 4 bedrooms

Western Branch North, Chesapeake, Virginia, United States

Internet

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$122 per night

House ∙ 6 guests ∙ 3 bedrooms

5.0

Outstanding (15 ratings)

Pleasant Grove West, Chesapeake, Virginia, United States

Internet

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$204 per night

House ∙ 6 guests ∙ 2 bedrooms

4.0

Very good (6 ratings)

Western Branch South, Chesapeake, Virginia, United States

Internet

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Vacation rentals with pool in Chesapeake

Discover best cabin and house rentals with pool in Chesapeake

$192 per night

Studio flat ∙ 3 guests ∙ 1 bedroom

Indian River, Chesapeake, Virginia, United States

Pool

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$245 per night

Condo ∙ 2 guests ∙ 1 bedroom

Indian River, Chesapeake, Virginia, United States

Pool

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$240 per night

Condo ∙ 4 guests ∙ 1 bedroom

Indian River, Chesapeake, Virginia, United States

Pool

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Best vacation rental offers in Chesapeake

$469 per night

House ∙ 9 guests ∙ 4 bedrooms

Western Branch South, Chesapeake, Virginia, United States

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$195 per night

House ∙ 2 guests ∙ 3 bedrooms

3.0

(3 ratings)

Indian River, Chesapeake, Virginia, United States

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$261 per night

House ∙ 8 guests ∙ 4 bedrooms

4.4

Very good (5 ratings)

Western Branch South, Chesapeake, Virginia, United States

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$147 per night

House ∙ 4 guests ∙ 2 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$246 per night

House ∙ 8 guests ∙ 4 bedrooms

South Norfolk, Chesapeake, Virginia, United States

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$209 per night

House ∙ 5 guests ∙ 2 bedrooms

Greenbrier West, Chesapeake, Virginia, United States

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$189 per night

House ∙ 5 guests ∙ 3 bedrooms

Great Bridge, Chesapeake, Virginia, United States

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$79 per night

House ∙ 3 guests ∙ 2 bedrooms

Great Bridge, Chesapeake, Virginia, United States

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$318 per night

House ∙ 9 guests ∙ 4 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$132 per night

House ∙ 5 guests ∙ 3 bedrooms

5.0

Outstanding (1 rating)

South Norfolk, Chesapeake, Virginia, United States

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$229 per night

House ∙ 8 guests ∙ 4 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$99 per night

Apartment ∙ 4 guests ∙ 2 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$137 per night

House ∙ 12 guests ∙ 3 bedrooms

4.5

Excellent (2 ratings)

Indian River, Chesapeake, Virginia, United States

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$146 per night

Apartment ∙ 2 guests ∙ 1 bedroom

Western Branch North, Chesapeake, Virginia, United States

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$214 per night

Apartment ∙ 4 guests ∙ 1 bedroom

South Norfolk, Chesapeake, Virginia, United States

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$141 per night

House ∙ 8 guests ∙ 4 bedrooms

4.7

Excellent (6 ratings)

Greenbrier West, Chesapeake, Virginia, United States

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$341 per night

House ∙ 4 guests ∙ 2 bedrooms

5.0

Outstanding (2 ratings)

Chesapeake, Virginia, United States

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$203 per night

Apartment ∙ 3 guests ∙ 1 bedroom

Indian River, Chesapeake, Virginia, United States

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$245 per night

Condo ∙ 6 guests ∙ 1 bedroom

Indian River, Chesapeake, Virginia, United States

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$87 per night

House ∙ 4 guests ∙ 2 bedrooms

Great Bridge, Chesapeake, Virginia, United States

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$110 per night

Apartment ∙ 2 guests ∙ 1 bedroom

Culpepper Landing, Chesapeake, Virginia, United States

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$134 per night

Resort ∙ 6 guests ∙ 1 bedroom

Deep Creek North, Chesapeake, Virginia, United States

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$137 per night

House ∙ 4 guests ∙ 2 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$124 per night

Apartment ∙ 2 guests ∙ 1 bedroom

Culpepper Landing, Chesapeake, Virginia, United States

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$60 per night

Motel ∙ 5 guests ∙ 1 bedroom

Deep Creek North, Chesapeake, Virginia, United States

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$135 per night

House ∙ 12 guests ∙ 3 bedrooms

Indian River, Chesapeake, Virginia, United States

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$132 per night

House ∙ 4 guests ∙ 2 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$284 per night

House ∙ 6 guests ∙ 3 bedrooms

Chesapeake, Virginia, United States

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Agoda

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$521 per night

House ∙ 4 guests ∙ 2 bedrooms

Western Branch North, Chesapeake, Virginia, United States

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$62 per night

Motel ∙ 4 guests ∙ 1 bedroom

3.0

(98 ratings)

Greenbrier West, Chesapeake, Virginia, United States

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$191 per night

House ∙ 6 guests ∙ 3 bedrooms

4.9

Outstanding (12 ratings)

South Norfolk, Chesapeake, Virginia, United States

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$171 per night

House ∙ 6 guests ∙ 3 bedrooms

4.4

Very good (10 ratings)

Western Branch North, Chesapeake, Virginia, United States

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$330 per night

House ∙ 8 guests ∙ 3 bedrooms

4.9

Outstanding (18 ratings)

South Norfolk, Chesapeake, Virginia, United States

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$326 per night

House ∙ 8 guests ∙ 4 bedrooms

4.0

Very good (6 ratings)

Western Branch North, Chesapeake, Virginia, United States

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$147 per night

House ∙ 6 guests ∙ 3 bedrooms

5.0

Outstanding (2 ratings)

Indian River, Chesapeake, Virginia, United States

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$154 per night

House ∙ 5 guests ∙ 3 bedrooms

4.7

Excellent (6 ratings)

Greenbrier West, Chesapeake, Virginia, United States

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$144 per night

House ∙ 6 guests ∙ 3 bedrooms

5.0

Outstanding (3 ratings)

Western Branch North, Chesapeake, Virginia, United States

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$296 per night

Condo ∙ 6 guests ∙ 2 bedrooms

4.6

Excellent (15 ratings)

Indian River, Chesapeake, Virginia, United States

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$258 per night

Condo ∙ 4 guests ∙ 1 bedroom

4.0

Very good (2 ratings)

Indian River, Chesapeake, Virginia, United States

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Chesapeake Vacation Rentals

Top deals for house rentals in Chesapeake

Pet-friendly rentals in Chesapeake

Accommodation with Internet in Chesapeake

Vacation rentals with pool in Chesapeake

Best vacation rental offers in Chesapeake

And we love our apartments

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