Chesapeake Vacation Rentals - Wimdu base64Hash Chesapeake Vacation Rentals - Wimdu

Chesapeake Vacation Rentals

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Choose from 736 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 $113 per night
Apartment ∙ 3 guests ∙ 1 bedroom

Rental apartment with BBQ, garden & patio

4.9
Outstanding(65 ratings)
Deep Creek South, Chesapeake, Virginia, United States
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House South Norfolk
from $320 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped nice house with barbeque

5.0
Outstanding(31 ratings)
South Norfolk, Chesapeake, Virginia, United States
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House Deep Creek North
from $246 per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, terrace & barbeque

5.0
Outstanding(22 ratings)
Deep Creek North, 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 $336 per night
House ∙ 8 guests ∙ 4 bedrooms

House with pool

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

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

Western Branch North, Chesapeake, Virginia, United States
Pet-friendly
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House Greenbrier West
from $714 per night
House ∙ 10 guests ∙ 4 bedrooms

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

Greenbrier West, Chesapeake, Virginia, United States
Pet-friendly
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Vacation rentals with pool in Chesapeake

Discover best cabin and house rentals with pool in Chesapeake

Condo Indian River
from $339 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with pool, hot tub & BBQ

Indian River, Chesapeake, Virginia, United States
Pool
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Condo Indian River
from $199 per night
Condo ∙ 4 guests ∙ 1 bedroom

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

Indian River, Chesapeake, Virginia, United States
Pool
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Condo Indian River
from $163 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with hot tub, grill & pool

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

Best vacation rental offers in Chesapeake

Motel Deep Creek North
from $131 per night
Motel ∙ 5 guests ∙ 1 bedroom

Motel for 5 persons

Deep Creek North, Chesapeake, Virginia, United States
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House Great Bridge
from $135 per night
House ∙ 3 guests ∙ 2 bedrooms

Vacation home with hot tub

5.0
Outstanding(3 ratings)
Great Bridge, Chesapeake, Virginia, United States
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Apartment South Norfolk
from $268 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Nice apartment with 1 room for 4 persons

South Norfolk, Chesapeake, Virginia, United States
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House Western Branch North
from $254 per night
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque & patio

4.5
Excellent(14 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Great Bridge
from $148 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 $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
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Condo South Norfolk
from $66 per night
Condo ∙ 2 guests ∙ 1 bedroom

Condo with 1 room for 2 persons

South Norfolk, Chesapeake, Virginia, United States
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House Pleasant Grove West
from $145 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden, grill & terrace | Nature view | Good for workation

5.0
Outstanding(33 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
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House Deep Creek North
from $255 per night
House ∙ 10 guests ∙ 5 bedrooms

House | Pets allowed

4.5
Excellent(8 ratings)
Deep Creek North, Chesapeake, Virginia, United States
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House Greenbrier West
from $575 per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with 3 rooms for 10 persons

Greenbrier West, Chesapeake, Virginia, United States
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House Western Branch South
from $770 per night
House ∙ 10 guests ∙ 5 bedrooms

Charming house with private pool & patio | Pets are welcome

4.0
Very good(1 rating)
Western Branch South, Chesapeake, Virginia, United States
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House Butts Station
from $155 per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace & barbeque | Perfect for remote work

5.0
Outstanding(86 ratings)
Butts Station, Chesapeake, Virginia, United States
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House Indian River
from $163 per night
House ∙ 4 guests ∙ 2 bedrooms

Child-friendly house with grill & terrace | Dogs allowed

5.0
Outstanding(10 ratings)
Indian River, Chesapeake, Virginia, United States
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Apartment Indian River
from $192 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental apartment with pool, hot tub & barbeque

5.0
Outstanding(6 ratings)
Indian River, Chesapeake, Virginia, United States
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Condo Indian River
from $241 per night
Condo ∙ 6 guests ∙ 1 bedroom

Fully equipped condo with hot tub, barbecue & pool

4.0
Very good(7 ratings)
Indian River, Chesapeake, Virginia, United States
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Cabin Greenbrier East
from $355 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Fully equipped charming cottage with barbecue | Perfect for remote work

Greenbrier East, Chesapeake, Virginia, United States
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Condo Indian River
from $250 per night
Condo ∙ 4 guests ∙ 1 bedroom

Condo with pool, barbeque & hot tub

Indian River, Chesapeake, Virginia, United States
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House Indian River
from $399 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with garden | Pets allowed

Indian River, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $181 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with garden

Western Branch North, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $127 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Holiday apartment with 2 rooms for 4 persons

Western Branch North, Chesapeake, Virginia, United States
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House Chesapeake
from $411 per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped house with garden & pool | Lake view

5.0
Outstanding(6 ratings)
Chesapeake, Virginia, United States
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House Western Branch North
from $282 per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly beautiful vacation home

4.4
Very good(21 ratings)
Western Branch North, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $96 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
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Studio flat Indian River
from $177 per night
Studio flat ∙ 3 guests ∙ 1 bedroom

Child-friendly studio with jacuzzi, pool & barbeque

Indian River, Chesapeake, Virginia, United States
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Aparthotel Western Branch North
from $147 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom

Fully equipped pleasant aparthotel with grill | Dogs allowed

Western Branch North, Chesapeake, Virginia, United States
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House Greenbrier West
from $799 per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with 3 rooms for 10 persons

Greenbrier West, Chesapeake, Virginia, United States
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House Western Branch South
from $880 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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Condo Indian River
from $270 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly nice condo with pool | Pets allowed

Indian River, Chesapeake, Virginia, United States
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Apartment Deep Creek West
from $173 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday apartment for 4 persons

Deep Creek West, Chesapeake, Virginia, United States
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Motel Western Branch South
from $75 per night
Motel ∙ 4 guests ∙ 1 bedroom

Motel for 4 persons

3.4
(234 ratings)
Western Branch South, Chesapeake, Virginia, United States
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Show all 786 apartments in Chesapeake

And we love our apartments

Motel for 5 persons
Vacation home with hot tub
Nice apartment with 1 room for 4 persons
House with barbeque & patio
Fully equipped pleasant house with hot tub
Show all 786 apartments in Chesapeake

Features of Chesapeake vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 306 rentals
🌙 Minimum price starting at $58
🐾 Pet friendly vacation homes 176 rentals
🏡 Rentals available 736 rentals

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