Chesapeake Vacation Rentals - Wimdu base64Hash Chesapeake Vacation Rentals - Wimdu

Chesapeake Vacation Rentals

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Anytime
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Choose from 752 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chesapeake

Discover vacation rentals with top-notch guest ratings

Apartment Deep Creek South
from $105 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental apartment with BBQ, garden & patio

4.9
Outstanding(68 ratings)
Deep Creek South, Chesapeake, Virginia, United States
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House Deep Creek North
from $208 per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, terrace & barbeque

5.0
Outstanding(34 ratings)
Deep Creek North, Chesapeake, Virginia, United States
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House Western Branch South
from $516 per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped nice vacation home with garden & terrace

5.0
Outstanding(7 ratings)
Western Branch South, 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

House Deep Creek South
from $328 per night
House ∙ 8 guests ∙ 4 bedrooms

House with pool

Deep Creek South, Chesapeake, Virginia, United States
Pet-friendly
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House Greenbrier West
from $805 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped wonderful house with jacuzzi, grill & private pool | Pet-friendly

Greenbrier West, Chesapeake, Virginia, United States
Pet-friendly
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Apartment Western Branch North
from $130 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with 2 bedrooms for 4 persons

Western Branch North, Chesapeake, Virginia, United States
Pet-friendly
View deal
See all pet-friendly offers

Vacation rentals with pool in Chesapeake

Discover best cabin and house rentals with pool in Chesapeake

Condo Indian River
from $203 per night
Condo ∙ 6 guests ∙ 1 bedroom

Child-friendly condo with pool, jacuzzi & barbeque

Indian River, Chesapeake, Virginia, United States
Pool
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Studio flat Indian River
from $163 per night
Studio flat ∙ 3 guests ∙ 1 bedroom

Studio with pool, hot tub & BBQ

Indian River, Chesapeake, Virginia, United States
Pool
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Condo Indian River
from $338 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool, hot tub & BBQ

Indian River, Chesapeake, Virginia, United States
Pool
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See all offers with pool

Best vacation rental offers in Chesapeake

House Indian River
from $376 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden | Pets allowed

Indian River, Chesapeake, Virginia, United States
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House Western Branch North
from $341 per night
House ∙ 4 guests ∙ 2 bedrooms

House with patio | Good for workation

4.8
Outstanding(17 ratings)
Western Branch North, Chesapeake, Virginia, United States
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Apartment Indian River
from $194 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Holiday apartment with hot tub, pool & barbecue | Good for workation

Indian River, Chesapeake, Virginia, United States
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House Greenbrier West
from $591 per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with jacuzzi

Greenbrier West, Chesapeake, Virginia, United States
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House South Norfolk
from $470 per night
House ∙ 5 guests ∙ 3 bedrooms

House with barbecue

South Norfolk, Chesapeake, Virginia, United States
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House Western Branch South
from $868 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with barbecue & yard

4.0
Very good(6 ratings)
Western Branch South, Chesapeake, Virginia, United States
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House Great Bridge
from $146 per night
House ∙ 3 guests ∙ 2 bedrooms

Vacation home with hot tub

5.0
Outstanding(5 ratings)
Great Bridge, Chesapeake, Virginia, United States
View deal
Motel Western Branch South
from $78 per night
Motel ∙ 2 guests ∙ 1 bedroom

Motel for 2 persons

3.5
Good(378 ratings)
Western Branch South, Chesapeake, Virginia, United States
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Motel Western Branch South
from $78 per night
Motel ∙ 4 guests ∙ 1 bedroom

Wonderful motel for 4 persons

3.5
Good(378 ratings)
Western Branch South, Chesapeake, Virginia, United States
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Motel Deep Creek North
from $84 per night
Motel ∙ 3 guests ∙ 1 bedroom

Motel for 3 persons

Deep Creek North, Chesapeake, Virginia, United States
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Motel Western Branch North
from $81 per night
Motel ∙ 2 guests ∙ 1 bedroom

Beautiful motel for 2 persons

Western Branch North, Chesapeake, Virginia, United States
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Motel Western Branch North
from $80 per night
Motel ∙ 3 guests ∙ 1 bedroom

Motel for 3 persons

Western Branch North, Chesapeake, Virginia, United States
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Motel Western Branch North
from $81 per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

Western Branch North, Chesapeake, Virginia, United States
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Motel Deep Creek North
from $89 per night
Motel ∙ 5 guests ∙ 1 bedroom

Motel for 5 persons

Deep Creek North, Chesapeake, Virginia, United States
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Motel Deep Creek North
from $89 per night
Motel ∙ 5 guests ∙ 1 bedroom

Motel for 5 persons

Deep Creek North, Chesapeake, Virginia, United States
View deal
Apartment Western Branch North
from $97 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment with yard, patio & jacuzzi | Suitable for remote work

4.0
Very good(1 rating)
Western Branch North, Chesapeake, Virginia, United States
View deal
Apartment Deep Creek West
from $172 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday apartment for 4 persons

Deep Creek West, Chesapeake, Virginia, United States
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Apartment South Norfolk
from $268 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Nice apartment with 1 bedroom for 4 persons

South Norfolk, Chesapeake, Virginia, United States
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House Chesapeake
from $393 per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house with garden & pool | Lake view

5.0
Outstanding(6 ratings)
Chesapeake, Virginia, United States
View deal
Studio flat Indian River
from $163 per night
Studio flat ∙ 3 guests ∙ 1 bedroom

Children-friendly nice studio with grill, pool & hot tub

Indian River, Chesapeake, Virginia, United States
View deal
House Indian River
from $283 per night
House ∙ 2 guests ∙ 3 bedrooms

Children-friendly pleasant vacation home | Perfect for remote work

4.0
Very good(6 ratings)
Indian River, Chesapeake, Virginia, United States
View deal
House Great Bridge
from $156 per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped pleasant house with hot tub

Great Bridge, Chesapeake, Virginia, United States
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House Indian River
from $177 per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard | Perfect for remote work

Indian River, Chesapeake, Virginia, United States
View deal
House Indian River
from $152 per night
House ∙ 4 guests ∙ 2 bedrooms

Child-friendly house with grill & terrace | Dogs allowed

4.9
Outstanding(16 ratings)
Indian River, Chesapeake, Virginia, United States
View deal
House South Norfolk
from $306 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped nice house with barbeque

5.0
Outstanding(32 ratings)
South Norfolk, Chesapeake, Virginia, United States
View deal
Apartment Western Branch North
from $179 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with garden

Western Branch North, Chesapeake, Virginia, United States
View deal
House Greenbrier West
from $262 per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped house with terrace & yard | Pet-friendly

Greenbrier West, Chesapeake, Virginia, United States
View deal
Apartment Greenbrier West
from $624 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday apartment with pool & fast internet

Greenbrier West, Chesapeake, Virginia, United States
View deal
House Western Branch North
from $262 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly beautiful vacation home

4.3
Very good(25 ratings)
Western Branch North, Chesapeake, Virginia, United States
View deal
Condo Indian River
from $176 per night
Condo ∙ 2 guests ∙ 1 bedroom

Child-friendly nice condo with grill, jacuzzi & pool

Indian River, Chesapeake, Virginia, United States
View deal
Show all 813 apartments in Chesapeake

And we love our apartments

Vacation home with garden | Pets allowed
House with patio | Good for workation
Holiday apartment with hot tub, pool & barbecue | Good for workation
Vacation home with jacuzzi
House with barbecue
Show all 813 apartments in Chesapeake

Features of Chesapeake vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 313 rentals
🌙 Minimum price starting at $65
🐾 Pet friendly vacation homes 189 rentals
🏡 Rentals available 752 rentals

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