Chesapeake Vacation Rentals - Wimdu base64Hash Chesapeake Vacation Rentals - Wimdu

Chesapeake Vacation Rentals

Anytime
1 guest
Anytime
1 guest
Choose from 736 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 $143 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(24 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Vrbo
View deal
House Butts Station
from $169 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(20 ratings)
Butts Station, Chesapeake, Virginia, United States
Vrbo
View deal
House Chesapeake
from $253 per night
House ∙ 11 guests ∙ 6 bedrooms
5.0
Outstanding(13 ratings)
Chesapeake, Virginia, United States
Vrbo
View deal

Pet-friendly rentals in Chesapeake

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

House Indian River
from $116 per night
House ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent(11 ratings)
Indian River, Chesapeake, Virginia, United States
Pet-friendly
Vrbo
View deal
Farmhouse Pleasant Grove West
from $208 per night
Farmhouse ∙ 5 guests ∙ 1 bedroom
4.8
Outstanding(10 ratings)
Pleasant Grove West, Chesapeake, Virginia, United States
Pet-friendly
Vrbo
View deal
House South Norfolk
from $299 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(27 ratings)
South Norfolk, Chesapeake, Virginia, United States
Pet-friendly
Vrbo
View deal
See all pet-friendly offers

Accommodation with Internet in Chesapeake

Choose your ideal rental with Internet and WiFi in Chesapeake

House Western Branch North
from $219 per night
House ∙ 8 guests ∙ 4 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Internet
HomeToGo
View deal
House Western Branch North
from $172 per night
House ∙ 6 guests ∙ 3 bedrooms
4.4
Very good(19 ratings)
Western Branch North, Chesapeake, Virginia, United States
Internet
Vrbo
View deal
House Great Bridge
from $273 per night
House ∙ 5 guests ∙ 3 bedrooms
4.6
Excellent(15 ratings)
Great Bridge, Chesapeake, Virginia, United States
Internet
Vrbo
View deal
See all offers with internet

Vacation rentals with pool in Chesapeake

Discover best cabin and house rentals with pool in Chesapeake

Studio flat Indian River
from $118 per night
Studio flat ∙ 3 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Pool
HomeToGo
View deal
Condo Indian River
from $345 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Indian River, Chesapeake, Virginia, United States
Pool
HomeToGo
View deal
Condo Indian River
from $289 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent(16 ratings)
Indian River, Chesapeake, Virginia, United States
Pool
Vrbo
View deal
See all offers with pool

Best vacation rental offers in Chesapeake

House Western Branch North
from $224 per night
House ∙ 8 guests ∙ 5 bedrooms
4.3
Very good(8 ratings)
Western Branch North, Chesapeake, Virginia, United States
Vrbo
View deal
House Greenbrier East
from $266 per night
House ∙ 6 guests ∙ 3 bedrooms
Greenbrier East, Chesapeake, Virginia, United States
Vrbo
View deal
House Western Branch South
from $482 per night
House ∙ 8 guests ∙ 4 bedrooms
Western Branch South, Chesapeake, Virginia, United States
Agoda
View deal
House Western Branch North
from $262 per night
House ∙ 8 guests ∙ 4 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Agoda
View deal
House Western Branch North
from $253 per night
House ∙ 8 guests ∙ 4 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Vio.com
View deal
House Western Branch North
from $186 per night
House ∙ 4 guests ∙ 2 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Vio.com
View deal
House Chesapeake
from $403 per night
House ∙ 4 guests ∙ 2 bedrooms
Chesapeake, Virginia, United States
Vio.com
View deal
Motel Western Branch North
from $71 per night
Motel ∙ 10 guests ∙ 1 bedroom
3.5
Good
Western Branch North, Chesapeake, Virginia, United States
Agoda
View deal
House Pleasant Grove West
from $172 per night
House ∙ 6 guests ∙ 3 bedrooms
Pleasant Grove West, Chesapeake, Virginia, United States
Vio.com
View deal
Apartment Deep Creek South
from $105 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Deep Creek South, Chesapeake, Virginia, United States
Vio.com
View deal
Motel Deep Creek North
from $72 per night
Motel ∙ 5 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
HomeToGo
View deal
House Indian River
from $286 per night
House ∙ 2 guests ∙ 3 bedrooms
4.0
Very good(6 ratings)
Indian River, Chesapeake, Virginia, United States
Vrbo
View deal
House Great Bridge
from $122 per night
House ∙ 3 guests ∙ 2 bedrooms
Great Bridge, Chesapeake, Virginia, United States
Vrbo
View deal
House Western Branch South
from $303 per night
House ∙ 8 guests ∙ 5 bedrooms
5.0
Outstanding(3 ratings)
Western Branch South, Chesapeake, Virginia, United States
Vrbo
View deal
House Indian River
from $422 per night
House ∙ 8 guests ∙ 3 bedrooms
4.8
Outstanding(10 ratings)
Indian River, Chesapeake, Virginia, United States
Vrbo
View deal
House Great Bridge
from $122 per night
House ∙ 4 guests ∙ 2 bedrooms
Great Bridge, Chesapeake, Virginia, United States
Vrbo
View deal
House Western Branch South
from $215 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(3 ratings)
Western Branch South, Chesapeake, Virginia, United States
Vrbo
View deal
House Western Branch North
from $146 per night
House ∙ 4 guests ∙ 2 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Vrbo
View deal
Condo South Norfolk
from $304 per night
Condo ∙ 5 guests ∙ 2 bedrooms
4.0
Very good(1 rating)
South Norfolk, Chesapeake, Virginia, United States
Vrbo
View deal
House Indian River
from $153 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(2 ratings)
Indian River, Chesapeake, Virginia, United States
Vrbo
View deal
House Western Branch North
from $142 per night
House ∙ 4 guests ∙ 2 bedrooms
Western Branch North, Chesapeake, Virginia, United States
Vrbo
View deal
Apartment Indian River
from $195 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Vrbo
View deal
Apartment South Norfolk
from $301 per night
Apartment ∙ 4 guests ∙ 1 bedroom
South Norfolk, Chesapeake, Virginia, United States
Vrbo
View deal
Apartment Western Branch North
from $90 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
Vrbo
View deal
House Greenbrier West
from $855 per night
House ∙ 10 guests ∙ 4 bedrooms
Greenbrier West, Chesapeake, Virginia, United States
Vio.com
View deal
Studio flat Indian River
from $133 per night
Studio flat ∙ 2 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
HomeToGo
View deal
House South Norfolk
from $294 per night
House ∙ 8 guests ∙ 3 bedrooms
South Norfolk, Chesapeake, Virginia, United States
Vio.com
View deal
Lodge South Norfolk
from $81 per night
Lodge ∙ 12 guests ∙ 4 bedrooms
South Norfolk, Chesapeake, Virginia, United States
Vio.com
View deal
Motel Western Branch South
from $69 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.4
(217 ratings)
Western Branch South, Chesapeake, Virginia, United States
HomeToGo
View deal
House Indian River
from $198 per night
House ∙ 6 guests ∙ 3 bedrooms
Indian River, Chesapeake, Virginia, United States
Vio.com
View deal
Motel Western Branch North
from $76 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
HomeToGo
View deal
Motel Western Branch North
from $76 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
HomeToGo
View deal
Motel Western Branch North
from $72 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
HomeToGo
View deal
Motel Western Branch South
from $69 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.4
(217 ratings)
Western Branch South, Chesapeake, Virginia, United States
HomeToGo
View deal
Motel Greenbrier West
from $57 per night
Motel ∙ 2 guests ∙ 1 bedroom
Greenbrier West, Chesapeake, Virginia, United States
Vio.com
View deal
Motel Western Branch North
from $69 per night
Motel ∙ 2 guests ∙ 1 bedroom
Western Branch North, Chesapeake, Virginia, United States
Vio.com
View deal
Motel Indian River
from $63 per night
Motel ∙ 2 guests ∙ 1 bedroom
Indian River, Chesapeake, Virginia, United States
Vio.com
View deal
Motel Deep Creek North
from $61 per night
Motel ∙ 3 guests ∙ 1 bedroom
Deep Creek North, Chesapeake, Virginia, United States
HomeToGo
View deal
Cottage Western Branch South
from $534 per night
Cottage ∙ 8 guests ∙ 4 bedrooms
Western Branch South, Chesapeake, Virginia, United States
HomeToGo
View deal
Show all 651 apartments in Chesapeake
222,698 reviews
222,698 travelers who stayed in Chesapeake rated their vacation home 3.5/5 stars on average.

And we love our apartments

223 m² House
House
223 m² House
223 m² House
House
Show all 651 apartments in Chesapeake

Features of Chesapeake vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 325 rentals
🌙 Minimum price starting at $55
🐾 Pet friendly vacation homes 178 rentals
🏡 Rentals available 736 rentals

Other Popular Vacation Destinations

Interesting destinations to consider for your next trip

Destinations worth visiting near Chesapeake

image-tag