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Chesapeake

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Vacation Rentals in Chesapeake, VA

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Rentals you can trust
Reviews by guests
Verified Listings
Most Trusted Travel Advice
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125 Trusted Chesapeake Area Rentals
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
1-20 of 125
Virginia Chesapeake Bay Beachfront, Chesapeake
United States, Virginia, Chesapeake Holiday Rentals
Virginia Chesapeake Bay Beachfront
Slideshow
4.5 of 5 stars 4 reviews
  • Holiday Rental House
  • 5 Bedrooms, sleeps 14
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
220 AUD
Week:
1,534 AUD
Minimum rental - 1 week
Check availability
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The following rentals are within 25 kilometres of Chesapeake, Virginia.

B-314 Beach Getaway, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-314 Beach Getaway
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
139 AUD - 349 AUD
Week:
667 AUD - 2,463 AUD
Minimum rental - 1 week
Check availability
Map unavailable
B-212 Summer Daze, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-212 Summer Daze
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
144 AUD - 359 AUD
Week:
708 AUD - 2,535 AUD
Minimum rental - 1 week
Check availability
Map unavailable
A-423 The Mac Shack, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
A-423 The Mac Shack
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
144 AUD - 369 AUD
Week:
729 AUD - 2,617 AUD
Minimum rental - 1 week
Check availability
Map unavailable
B-213 Coastal Edge II, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-213 Coastal Edge II
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
174 AUD - 441 AUD
Week:
883 AUD - 3,166 AUD
Minimum rental - 1 week
Check availability
Map unavailable
A-306 Infinite Horizon, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
A-306 Infinite Horizon
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Week:
1,021 AUD - 3,684 AUD
Minimum rental - 1 week
Check availability
Map unavailable
B-210 MariSol, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-210 MariSol
Slideshow
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 9
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
205 AUD - 503 AUD
Week:
1,006 AUD - 3,602 AUD
Minimum rental - 1 week
Check availability
Map unavailable
A-319 Heron's Nest, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
A-319 Heron's Nest
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
144 AUD - 369 AUD
Week:
717 AUD - 2,638 AUD
Minimum rental - 1 week
Check availability
Map unavailable
A-109 Aria Di Mare, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
A-109 Aria Di Mare
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
164 AUD - 400 AUD
Week:
800 AUD - 2,884 AUD
Minimum rental - 1 week
Check availability
Map unavailable
A-204 Oceanfront Oasis, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
A-204 Oceanfront Oasis
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
195 AUD - 493 AUD
Week:
919 AUD - 3,484 AUD
Minimum rental - 1 week
Check availability
Map unavailable
B-414 Adagio, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-414 Adagio
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
257 AUD - 411 AUD
Week:
975 AUD - 2,668 AUD
Minimum rental - 1 week
Check availability
Map unavailable
Seashore Delight- Ocean Side- Spacious Condo, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
Seashore Delight- Ocean Side- Spacious Condo
Slideshow
4.5 of 5 stars 5 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
1,232 AUD - 2,206 AUD
Minimum rental - 3 nights
Check availability
Show on map
B-106 Sandy Bottoms, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-106 Sandy Bottoms
Slideshow
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
216 AUD - 544 AUD
Week:
1,088 AUD - 3,859 AUD
Minimum rental - 1 week
Check availability
Map unavailable
B-412 The Great Escape, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-412 The Great Escape
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 9
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
144 AUD - 359 AUD
Week:
718 AUD - 2,566 AUD
Minimum rental - 1 week
Check availability
Map unavailable
A-123 Mango Tango, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
A-123 Mango Tango
Slideshow
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 9
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
133 AUD - 359 AUD
Week:
667 AUD - 2,566 AUD
Minimum rental - 1 week
Check availability
Map unavailable
B-209 Jornica, Virginia Beach
United States, Virginia, Virginia Beach Holiday Rentals
B-209 Jornica
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
205 AUD - 513 AUD
Week:
1,037 AUD - 3,684 AUD
Minimum rental - 1 week
Check availability
Map unavailable
1-20 of 125

Chesapeake Holiday Rental Advice

Where to stay & see harbor activity?
Posted by Wendymath, 23 Jun 2009
... a river, try finding a vacation rental in "Chick's Beach." That's the local nickname for Chesapeake Bay beach. If I haven't come even close to helping you, then post again and give some more information and I'll try to think of something else. Maybe others will ... more
Go to Chesapeake Forums »