Chesapeake Vacation Rentals - Wimdu base64Hash Chesapeake Vacation Rentals - Wimdu

Chesapeake Vacation Rentals

Anytime
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Anytime
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Choose from 713 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chesapeake

Discover vacation rentals with top-notch guest ratings

House Pleasant Grove West
from $131 per night
House ∙ 6 guests ∙ 3 bedrooms

121 m² House

5.0
Outstanding(25 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
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House Great Bridge
from $255 per night
5 guests ∙ 3 bedrooms

House

4.8
Outstanding(25 ratings)
Great Bridge, Chesapeake, Virginia, United States
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Farmhouse Pleasant Grove West
from $210 per night
Farmhouse ∙ 5 guests ∙ 1 bedroom

372 m² Farmhouse

4.8
Outstanding(10 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 West
from $805 per night
10 guests ∙ 4 bedrooms

House

Greenbrier West, Chesapeake, Virginia, United States
Pet-friendly
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Apartment Western Branch South
from $37 per night
2 guests ∙ 1 bedroom

Apartment

Western Branch South, Chesapeake, Virginia, United States
Pet-friendly
View deal
House Indian River
from $148 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(4 ratings)
Indian River, 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 $329 per night
6 guests ∙ 2 bedrooms

Condo

Indian River, Chesapeake, Virginia, United States
Pool
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House Chesapeake
from $402 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Chesapeake, Virginia, United States
Pool
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Condo Indian River
from $451 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 $240 per night
House ∙ 8 guests ∙ 4 bedrooms

222 m² House

3.7
Good(3 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Western Branch North
from $157 per night
House ∙ 4 guests ∙ 2 bedrooms

93 m² House

4.9
Outstanding(9 ratings)
Western Branch North, Chesapeake, Virginia, United States
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House Western Branch South
from $332 per night
9 guests ∙ 4 bedrooms

House

4.4
Very good(24 ratings)
Western Branch South, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $88 per night
2 guests ∙ 1 bedroom

Apartment

Western Branch North, Chesapeake, Virginia, United States
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House Great Bridge
from $114 per night
House ∙ 4 guests ∙ 2 bedrooms

84 m² House

Great Bridge, Chesapeake, Virginia, United States
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House Indian River
from $162 per night
12 guests ∙ 3 bedrooms

House

Indian River, Chesapeake, Virginia, United States
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House Western Branch South
from $225 per night
6 guests ∙ 3 bedrooms

House

4.7
Excellent(7 ratings)
Western Branch South, Chesapeake, Virginia, United States
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House Great Bridge
from $137 per night
House ∙ 3 guests ∙ 2 bedrooms

84 m² House

Great Bridge, Chesapeake, Virginia, United States
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House Greenbrier East
from $233 per night
House ∙ 7 guests ∙ 3 bedrooms

136 m² House

5.0
Outstanding(7 ratings)
Greenbrier East, Chesapeake, Virginia, United States
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House Indian River
from $280 per night
House ∙ 6 guests ∙ 3 bedrooms

83 m² House

4.6
Excellent(13 ratings)
Indian River, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $126 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

102 m² Apartment

Western Branch North, Chesapeake, Virginia, United States
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House Western Branch South
from $213 per night
6 guests ∙ 2 bedrooms

House

4.0
Very good(6 ratings)
Western Branch South, Chesapeake, Virginia, United States
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House Indian River
from $199 per night
12 guests ∙ 3 bedrooms

House

Indian River, Chesapeake, Virginia, United States
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House Indian River
from $282 per night
House ∙ 2 guests ∙ 3 bedrooms

205 m² House

4.0
Very good(6 ratings)
Indian River, Chesapeake, Virginia, United States
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Cabin Western Branch South
from $778 per night
Cabin ∙ 8 guests ∙ 4 bedrooms

222 m² Cabin

Western Branch South, Chesapeake, Virginia, United States
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House Indian River
from $330 per night
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

Indian River, Chesapeake, Virginia, United States
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House South Norfolk
from $275 per night
8 guests ∙ 3 bedrooms

House

4.9
Outstanding(29 ratings)
South Norfolk, Chesapeake, Virginia, United States
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House Western Branch North
from $357 per night
House ∙ 8 guests ∙ 4 bedrooms

223 m² House

Western Branch North, Chesapeake, Virginia, United States
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Apartment Western Branch North
from $129 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 $208 per night
House ∙ 4 guests ∙ 2 bedrooms

93 m² House

Western Branch North, Chesapeake, Virginia, United States
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House Deep Creek North
from $282 per night
7 guests ∙ 4 bedrooms

House

Deep Creek North, Chesapeake, Virginia, United States
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Motel Western Branch North
from $79 per night
Motel ∙ 10 guests ∙ 1 bedroom

Budget Lodge Churchland

3.5
Good
Western Branch North, Chesapeake, Virginia, United States
View deal
Motel Western Branch South
from $73 per night
Motel ∙ 2 guests ∙ 1 bedroom

27 m² Motel

3.4
(223 ratings)
Western Branch South, 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 South
from $73 per night
Motel ∙ 4 guests ∙ 1 bedroom

27 m² Motel

3.4
(223 ratings)
Western Branch South, Chesapeake, Virginia, United States
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Motel Western Branch North
from $81 per night
Motel ∙ 2 guests ∙ 1 bedroom

20 m² Motel

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

Motel

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

20 m² Motel

Western Branch North, Chesapeake, Virginia, United States
View deal
Motel Deep Creek North
from $85 per night
5 guests ∙ 1 bedroom

Motel

Deep Creek North, Chesapeake, Virginia, United States
View deal
Motel Indian River
from $91 per night
2 guests ∙ 1 bedroom

Motel

Indian River, Chesapeake, Virginia, United States
View deal
Show all 653 apartments in Chesapeake

And we love our apartments

222 m² House
93 m² House
House
Apartment
84 m² House
Show all 653 apartments in Chesapeake

Features of Chesapeake vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 319 rentals
🌙 Minimum price starting at $60
🐾 Pet friendly vacation homes 175 rentals
🏡 Rentals available 713 rentals

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