Chesapeake Vacation Rentals - Wimdu base64Hash Chesapeake Vacation Rentals - Wimdu

Chesapeake Vacation Rentals

Anytime
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Anytime
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Choose from 702 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 $98 per night
Apartment ∙ 3 guests ∙ 1 bedroom

37 m² Apartment

4.9
Outstanding(66 ratings)
Deep Creek South, Chesapeake, Virginia, United States
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House Great Bridge
from $241 per night
5 guests ∙ 3 bedrooms

House

4.9
Outstanding(34 ratings)
Great Bridge, Chesapeake, Virginia, United States
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House Pleasant Grove West
from $121 per night
House ∙ 6 guests ∙ 3 bedrooms

121 m² House

5.0
Outstanding(29 ratings)
Pleasant Grove West, 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 Greenbrier East
from $205 per night
House ∙ 7 guests ∙ 3 bedrooms

136 m² House

5.0
Outstanding(19 ratings)
Greenbrier East, Chesapeake, Virginia, United States
Pet-friendly
View deal
House Butts Station
from $159 per night
House ∙ 6 guests ∙ 3 bedrooms

148 m² House

5.0
Outstanding(63 ratings)
Butts Station, Chesapeake, Virginia, United States
Pet-friendly
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House Greenbrier West
from $797 per night
10 guests ∙ 4 bedrooms

House

Greenbrier West, Chesapeake, Virginia, United States
Pet-friendly
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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 $357 per night
6 guests ∙ 2 bedrooms

Condo

Indian River, Chesapeake, Virginia, United States
Pool
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House Chesapeake
from $359 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Chesapeake, Virginia, United States
Pool
View deal
Condo Indian River
from $386 per night
6 guests ∙ 2 bedrooms

Condo

4.7
Excellent(16 ratings)
Indian River, Chesapeake, Virginia, United States
Pool
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See all offers with pool

Best vacation rental offers in Chesapeake

House Western Branch North
from $224 per night
House ∙ 4 guests ∙ 2 bedrooms

93 m² House

4.9
Outstanding(47 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Great Bridge
from $134 per night
House ∙ 3 guests ∙ 2 bedrooms

84 m² House

5.0
Outstanding(1 rating)
Great Bridge, Chesapeake, Virginia, United States
View deal
Cabin Greenbrier East
from $233 per night
Cabin ∙ 8 guests ∙ 3 bedrooms

92 m² Cabin

Greenbrier East, Chesapeake, Virginia, United States
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House Great Bridge
from $149 per night
House ∙ 4 guests ∙ 2 bedrooms

84 m² House

Great Bridge, Chesapeake, Virginia, United States
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House Greenbrier West
from $250 per night
8 guests ∙ 4 bedrooms

House

Greenbrier West, Chesapeake, Virginia, United States
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House Western Branch North
from $219 per night
House ∙ 6 guests ∙ 3 bedrooms

176 m² House

4.5
Excellent(14 ratings)
Western Branch North, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $125 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

102 m² Apartment

Western Branch North, Chesapeake, Virginia, United States
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House Western Branch North
from $217 per night
House ∙ 8 guests ∙ 4 bedrooms

223 m² House

4.4
Very good(20 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Deep Creek North
from $233 per night
10 guests ∙ 5 bedrooms

House

4.4
Very good(6 ratings)
Deep Creek North, Chesapeake, Virginia, United States
View deal
House Deep Creek South
from $247 per night
8 guests ∙ 4 bedrooms

House

Deep Creek South, Chesapeake, Virginia, United States
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House Deep Creek North
from $295 per night
7 guests ∙ 4 bedrooms

House

5.0
Outstanding(5 ratings)
Deep Creek North, Chesapeake, Virginia, United States
View deal
House Indian River
from $241 per night
House ∙ 2 guests ∙ 3 bedrooms

205 m² House

4.0
Very good(6 ratings)
Indian River, Chesapeake, Virginia, United States
View deal
House South Norfolk
from $386 per night
5 guests ∙ 3 bedrooms

House

South Norfolk, Chesapeake, Virginia, United States
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Apartment Indian River
from $166 per night
3 guests ∙ 1 bedroom

Apartment

Indian River, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $94 per night
2 guests ∙ 1 bedroom

Apartment

4.0
Very good(1 rating)
Western Branch North, Chesapeake, Virginia, United States
View deal
House Greenbrier West
from $547 per night
10 guests ∙ 3 bedrooms

House

Greenbrier West, Chesapeake, Virginia, United States
View deal
House Western Branch South
from $228 per night
6 guests ∙ 3 bedrooms

House

4.8
Outstanding(30 ratings)
Western Branch South, Chesapeake, Virginia, United States
View deal
House Indian River
from $273 per night
House ∙ 6 guests ∙ 3 bedrooms

109 m² House

Indian River, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $127 per night
2 guests ∙ 1 bedroom

Apartment

Western Branch North, Chesapeake, Virginia, United States
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Studio flat Indian River
from $142 per night
3 guests ∙ 1 bedroom

Studio flat

Indian River, Chesapeake, Virginia, United States
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Apartment South Norfolk
from $275 per night
4 guests ∙ 1 bedroom

Apartment

South Norfolk, Chesapeake, Virginia, United States
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Motel Western Branch South
from $73 per night
Motel ∙ 2 guests ∙ 1 bedroom

27 m² Motel

3.4
(234 ratings)
Western Branch South, Chesapeake, Virginia, United States
View deal
Motel Western Branch South
from $73 per night
Motel ∙ 4 guests ∙ 1 bedroom

27 m² Motel

3.4
(234 ratings)
Western Branch South, Chesapeake, Virginia, United States
View deal
Motel Deep Creek North
from $72 per night
3 guests ∙ 1 bedroom

Motel

Deep Creek North, Chesapeake, Virginia, United States
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Motel Western Branch North
from $79 per night
Motel ∙ 2 guests ∙ 1 bedroom

20 m² Motel

Western Branch North, Chesapeake, Virginia, United States
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Motel Western Branch North
from $77 per night
Motel ∙ 2 guests ∙ 1 bedroom

20 m² Motel

Western Branch North, Chesapeake, Virginia, United States
View deal
Motel Western Branch North
from $79 per night
Motel ∙ 2 guests ∙ 1 bedroom

20 m² Motel

Western Branch North, Chesapeake, Virginia, United States
View deal
Motel Deep Creek North
from $78 per night
5 guests ∙ 1 bedroom

Motel

Deep Creek North, Chesapeake, Virginia, United States
View deal
House Indian River
from $425 per night
8 guests ∙ 3 bedrooms

House

4.8
Outstanding(10 ratings)
Indian River, Chesapeake, Virginia, United States
View deal
House South Norfolk
from $278 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(31 ratings)
South Norfolk, Chesapeake, Virginia, United States
View deal
Show all 767 apartments in Chesapeake

And we love our apartments

93 m² House
84 m² House
92 m² Cabin
84 m² House
House
Show all 767 apartments in Chesapeake

Features of Chesapeake vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 292 rentals
🌙 Minimum price starting at $55
🐾 Pet friendly vacation homes 171 rentals
🏡 Rentals available 702 rentals

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