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Compare 1441 Vacation Homes in Chesapeake with updated reviews, rates, and availability.

Your own private beach with this charming 3-bedroom beachfront house!
Your own private beach with this charming 3-bedroom beachfront house!

Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~
Brand NEW POOL for 2025~Oceanfront Home “Sea Watch”~REDUCED RATES APRIL AND MAY~
10.0 out of 10, Exceptional, (3)

Super close to beaches, the historic triangle, and bush gardens!
Super close to beaches, the historic triangle, and bush gardens!
8.4 out of 10, Very Good, (26)

Spacious oceanfront house w/beach access, decks, grill & free WIFI
Spacious oceanfront house w/beach access, decks, grill & free WIFI

Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi
Dog-friendly home with private pool, fenced yard, ocean view, nice deck & WiFi
7.0 out of 10, Good, (20)

The Art Door only minutes from beach
The Art Door only minutes from beach
9.6 out of 10, Exceptional, (65)
The price is SAR 416
SAR 922 total
includes taxes & fees
1 Apr - 2 Apr

Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly
Oceanside beach home private outdoor pool, fast WiFi & W/D - dog-friendly
8.4 out of 10, Very Good, (25)

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
9.4 out of 10, Exceptional, (13)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chesapeake

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
8.0 out of 10, Very Good, (1158)
The price is SAR 334
SAR 607 total
includes taxes & fees
9 Apr - 10 Apr

The Ocean Key Virginia Beach Resort
The Ocean Key Virginia Beach Resort
7.8 out of 10, Good, (1303)
The price is SAR 334
SAR 607 total
includes taxes & fees
9 Apr - 10 Apr

The Atrium Resort, Virginia Beach by Vacatia
The Atrium Resort, Virginia Beach by Vacatia
8.2 out of 10, Very Good, (1302)
The price is SAR 214
SAR 469 total
includes taxes & fees
1 Apr - 2 Apr
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Chesapeake hotels
Recent reviews of Chesapeake hotels

Hyatt Place Virginia Beach / Oceanfront
5/5 Excellent
"All the views from the windows. Comfortable bed and space for me and my partner "
A verified traveler stayed at Hyatt Place Virginia Beach / Oceanfront
Posted 7 hours ago