Chesapeake Bay Vacation Rentals - Wimdu base64Hash Chesapeake Bay Vacation Rentals - Wimdu

Chesapeake Bay Vacation Rentals

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Choose from 12,566 vacation rentals and homes for your trip!

Best-rated vacation rentals in Chesapeake Bay

Discover vacation rentals with top-notch guest ratings

House Betterton
from $339 per night
House ∙ 11 guests ∙ 6 bedrooms

158 m² House

4.8
Outstanding(128 ratings)
Betterton, Worton (Betterton), Maryland, United States
Vrbo
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House Pasadena
from $524 per night
House ∙ 14 guests ∙ 6 bedrooms

279 m² House

4.7
Excellent(97 ratings)
Pasadena, Anne Arundel County, Maryland, United States
Vrbo
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House Fox Hill - Grandview
from $425 per night
House ∙ 12 guests ∙ 4 bedrooms

313 m² House

4.5
Excellent(48 ratings)
Fox Hill - Grandview, Hampton, Virginia, United States
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Pet-friendly rentals in Chesapeake Bay

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

House Cape Charles
from $679 per night
10 guests ∙ 4 bedrooms

House

Cape Charles, Northampton County, Virginia, United States
Pet-friendly
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House Port Haywood
from $259 per night
House ∙ 8 guests ∙ 4 bedrooms

214 m² House

5.0
Outstanding(160 ratings)
Port Haywood, Chesapeake, Virginia, United States
Pet-friendly
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House Reedville
from $235 per night
House ∙ 10 guests ∙ 4 bedrooms

339 m² House

4.9
Outstanding(6 ratings)
Reedville, Northumberland County, Virginia, United States
Pet-friendly
Vrbo
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Vacation rentals with pool in Chesapeake Bay

Discover best cabin and house rentals with pool in Chesapeake Bay

House Annapolis Cove
from $1,391 per night
House ∙ 10 guests ∙ 5 bedrooms

319 m² House

4.9
Outstanding(7 ratings)
Annapolis Cove, Anne Arundel County, Maryland, United States
Pool
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House Dam Neck
from $716 per night
House ∙ 12 guests ∙ 6 bedrooms

339 m² House

4.9
Outstanding(77 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Pool
Vrbo
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House Cape Charles
from $294 per night
House ∙ 9 guests ∙ 3 bedrooms

158 m² House

4.8
Outstanding(11 ratings)
Cape Charles, Northampton County, Virginia, United States
Pool
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Best vacation rental offers in Chesapeake Bay

House Northeast Virginia Beach
from $680 per night
12 guests ∙ 5 bedrooms

House

Northeast Virginia Beach, Virginia Beach, Virginia, United States
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House Deale
from $288 per night
6 guests ∙ 3 bedrooms

House

Deale, Anne Arundel County, Maryland, United States
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House Chic's Beach
from $206 per night
House ∙ 10 guests ∙ 4 bedrooms

137 m² House

4.8
Outstanding(18 ratings)
Chic's Beach, Virginia Beach, Virginia, United States
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House Lake Shore
from $147 per night
15 guests ∙ 7 bedrooms

House

4.9
Outstanding(79 ratings)
Lake Shore, Anne Arundel County, Maryland, United States
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Cottage Scotland
from $377 per night
12 guests ∙ 6 bedrooms

Cottage

4.9
Outstanding(11 ratings)
Scotland, St. Inigoes, Maryland, United States
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House Stevensville
from $314 per night
House ∙ 20 guests ∙ 5 bedrooms

343 m² House

5.0
Outstanding(229 ratings)
Stevensville, Kent Island, Maryland, United States
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House Buckroe Beach
from $653 per night
14 guests ∙ 7 bedrooms

House

4.8
Outstanding(9 ratings)
Buckroe Beach, Hampton, Virginia, United States
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House Perryville
from $804 per night
16 guests ∙ 5 bedrooms

House

5.0
Outstanding(15 ratings)
Perryville, Cecil County, Maryland, United States
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House Chesapeake Ranch Estates-Drum Point
from $357 per night
House ∙ 11 guests ∙ 5 bedrooms

174 m² House

4.9
Outstanding(22 ratings)
Chesapeake Ranch Estates-Drum Point, Solomons Island, Maryland, United States
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House Heathsville
from $384 per night
House ∙ 11 guests ∙ 6 bedrooms

186 m² House

5.0
Outstanding(17 ratings)
Heathsville, Northumberland County, Virginia, United States
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House Reedville
from $315 per night
House ∙ 8 guests ∙ 4 bedrooms

278 m² House

4.8
Outstanding(40 ratings)
Reedville, Northumberland County, Virginia, United States
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House Dam Neck
from $263 per night
House ∙ 11 guests ∙ 4 bedrooms

171 m² House

4.2
Very good(32 ratings)
Dam Neck, Virginia Beach, Virginia, United States
Vrbo
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House Reedville
from $230 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(6 ratings)
Reedville, Northumberland County, Virginia, United States
Vrbo
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House Northeast Virginia Beach
from $485 per night
House ∙ 13 guests ∙ 6 bedrooms

316 m² House

5.0
Outstanding(16 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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House Heathsville
from $248 per night
House ∙ 10 guests ∙ 5 bedrooms

158 m² House

4.9
Outstanding(59 ratings)
Heathsville, Northumberland County, Virginia, United States
Vrbo
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House Willoughby Spit
from $452 per night
12 guests ∙ 5 bedrooms

House

4.7
Excellent(25 ratings)
Willoughby Spit, Norfolk, Virginia, United States
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House Portsmouth
from $166 per night
House ∙ 8 guests ∙ 4 bedrooms

130 m² House

4.9
Outstanding(25 ratings)
Portsmouth, Virginia, United States
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House Palmer
from $472 per night
House ∙ 14 guests ∙ 4 bedrooms

263 m² House

4.8
Outstanding(59 ratings)
Palmer, Lancaster County, Virginia, United States
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House Cape Charles
from $1,734 per night
House ∙ 18 guests ∙ 6 bedrooms

353 m² House

4.8
Outstanding(35 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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House Cape Charles
from $763 per night
House ∙ 12 guests ∙ 5 bedrooms

335 m² House

5.0
Outstanding(62 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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House Bay View
from $362 per night
House ∙ 8 guests ∙ 4 bedrooms

195 m² House

Bay View, Norfolk, Virginia, United States
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House Pasadena
from $771 per night
14 guests ∙ 4 bedrooms

House

5.0
Outstanding
Pasadena, Anne Arundel County, Maryland, United States
Vacasa
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House Northeast Virginia Beach
from $730 per night
12 guests ∙ 6 bedrooms

House

5.0
Outstanding(4 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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House Cape Charles
from $459 per night
House ∙ 7 guests ∙ 3 bedrooms

204 m² House

Cape Charles, Northampton County, Virginia, United States
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House Norfolk
from $153 per night
6 guests ∙ 4 bedrooms

House

4.3
Very good(11 ratings)
Norfolk, Virginia, United States
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House Tracys Landing
from $1,323 per night
House ∙ 20 guests ∙ 7 bedrooms

325 m² House

4.9
Outstanding(68 ratings)
Tracys Landing, Anne Arundel County, Maryland, United States
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House Cambridge
from $447 per night
13 guests ∙ 8 bedrooms

House

5.0
Outstanding(6 ratings)
Cambridge, Dorchester County, Maryland, United States
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House Northeast Virginia Beach
from $422 per night
House ∙ 10 guests ∙ 5 bedrooms

186 m² House

5.0
Outstanding(26 ratings)
Northeast Virginia Beach, Virginia Beach, Virginia, United States
Vrbo
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House White Stone
from $378 per night
13 guests ∙ 5 bedrooms

House

White Stone, Lancaster County, Virginia, United States
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House Cape Charles
from $526 per night
House ∙ 10 guests ∙ 5 bedrooms

260 m² House

4.8
Outstanding(30 ratings)
Cape Charles, Northampton County, Virginia, United States
Vrbo
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Show all 12206 apartments in Chesapeake Bay
2,354,670 reviews
2,354,670 travelers who stayed in Chesapeake Bay rated their vacation home 4.3/5 stars on average.

And we love our apartments

House
House
137 m² House
House
Cottage
Show all 12206 apartments in Chesapeake Bay

Features of Chesapeake Bay vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🏊  Vacation rentals with a pool 4,712 rentals
🌙 Minimum price starting at $71
🐾 Pet friendly vacation homes 3,755 rentals
🏡 Rentals available 12,566 rentals

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Beautiful regions near to consider for next trip

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