Cozy 2 Bdrm Cottage King bed 
Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match 25+ Vacation Rentals Near Chesapeake
NearbyHoliday - Vacation Rentals in Chesapeake
Cozy Portsmouth Retreat 2BR 1BA Best Price Match
9.8 (6 Reviews) Holiday_home
The entire place is yours • 102 m² size • Free WiFi
Best Price Match 
Bright Chesapeake Home Near Shopping and Dining Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • 93 m² size • Kitchen
Best Price Match 
Spacious Chesapeake Home with Pool Table! Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • 223 m² size • On-site parking
Best Price Match 
Portsmouth 2BR 1BA Getaway Best Price Match
7.0 (3 Reviews) Holiday_home
The entire place is yours • 102 m² size • Free WiFi
Best Price Match Luxury Places to Stay in Chesapeake
Over 3+ Luxury Places to Stay in or Near Chesapeake
Hilton Norfolk The Main Best Price Match
8.6 (370 Reviews) Hotel
Breakfast • On-site parking • Indoor swimming pool
Best Price Match 
Renaissance Portsmouth-Norfolk Waterfront Hotel Best Price Match
8.1 (476 Reviews) Hotel
Breakfast • On-site parking • Indoor swimming pool
Best Price Match Cozy Portsmouth Retreat 2BR 1BA Best Price Match
9.8 (6 Reviews) Holiday_home
The entire place is yours • 102 m² size • Free WiFi
Best Price Match Pet-Friendly Vacation Rentals in Chesapeake
Over 4+ Pet-Friendly Vacation Rentals in or Near Chesapeake
Cozy 2 Bdrm Cottage King bed Pets allowed Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match 
Red Roof Inn Norfolk - Portsmouth Pets allowed Best Price Match
6.3 (229 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match 
Motel 6-Portsmouth, VA Pets allowed Best Price Match
4.8 (169 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match 
YourSpace Hotels Chesapeake Pets allowed Best Price Match
9.7 (11 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match Vacation Rentals in Chesapeake
Over 5+ Vacation Rentals in or Near Chesapeake
Cozy 2 Bdrm Cottage King bed Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • Free on-site parking • Pet friendly
Best Price Match Cozy Portsmouth Retreat 2BR 1BA Best Price Match
9.8 (6 Reviews) Holiday_home
The entire place is yours • 102 m² size • Free WiFi
Best Price Match Bright Chesapeake Home Near Shopping and Dining Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • 93 m² size • Kitchen
Best Price Match Spacious Chesapeake Home with Pool Table! Best Price Match
9.3 (3 Reviews) Holiday_home
The entire place is yours • 223 m² size • On-site parking
Best Price Match Portsmouth 2BR 1BA Getaway Best Price Match
7.0 (3 Reviews) Holiday_home
The entire place is yours • 102 m² size • Free WiFi
Best Price Match Hotels in Chesapeake
Over 20+ Hotels in or Near Chesapeake
Comfort Inn & Suites Chesapeake - Portsmouth Best Price Match
5.9 (308 Reviews) Hotel
Breakfast • Free on-site parking • 2 swimming pools
Best Price Match 
Bowers Hill Inn Chesapeake Best Price Match
5.5 (296 Reviews) Hotel
Free on-site parking • Free WiFi • Private bathroom
Best Price Match 
Days Inn by Wyndham Chesapeake Best Price Match
5.9 (233 Reviews) Hotel
Breakfast • Free WiFi • Private bathroom
Best Price Match 
American Inn Chesapeake - Portsmouth Best Price Match
6.1 (164 Reviews) Hotel
Free on-site parking • Free WiFi • Private bathroom
Best Price Match 
Holiday Inn Express & Suites Chesapeake by IHG Best Price Match
7.3 (402 Reviews) Hotel
Breakfast • Free on-site parking • Indoor swimming pool
Best Price Match Renaissance Portsmouth-Norfolk Waterfront Hotel Best Price Match
8.1 (476 Reviews) Hotel
Breakfast • On-site parking • Indoor swimming pool
Best Price Match Hilton Norfolk The Main Best Price Match
8.6 (370 Reviews) Hotel
Breakfast • On-site parking • Indoor swimming pool
Best Price Match 
Quality Inn & Suites Olde Town Best Price Match
7.3 (402 Reviews) Hotel
Breakfast • Free on-site parking • Free WiFi
Best Price Match Cheap Places to Stay in Chesapeake
Over 20+ Cheap Places to Stay in or Near Chesapeake
Bowers Hill Inn Chesapeake Best Price Match
5.5 (296 Reviews) Hotel
Free on-site parking • Free WiFi • Private bathroom
Best Price Match American Inn Chesapeake - Portsmouth Best Price Match
6.1 (164 Reviews) Hotel
Free on-site parking • Free WiFi • Private bathroom
Best Price Match Days Inn by Wyndham Chesapeake Best Price Match
5.9 (233 Reviews) Hotel
Breakfast • Free WiFi • Private bathroom
Best Price Match Comfort Inn & Suites Chesapeake - Portsmouth Best Price Match
5.9 (308 Reviews) Hotel
Breakfast • Free on-site parking • 2 swimming pools
Best Price Match 
Studios 4 Less Chesapeake Best Price Match
6.0 (17 Reviews) Hotel
Free on-site parking • Private bathroom • Bathtub
Best Price Match 
Super 8 by Wyndham Portsmouth - Norfolk Best Price Match
4.0 (178 Reviews) Motel
On-site parking • Wifi • Private bathroom
Best Price Match 
Economy Lodge Portsmouth Best Price Match
3.4 (60 Reviews) Motel
Free on-site parking • Free WiFi • Private bathroom
Best Price Match Motel 6-Portsmouth, VA Best Price Match
4.8 (169 Reviews) Hotel
Free on-site parking • Pet friendly • Free WiFi
Best Price Match Hotels with Suites in Chesapeake
Over 8+ Hotels with Suites in or Near Chesapeake
Comfort Inn & Suites Chesapeake - Portsmouth Best Price Match
5.9 (308 Reviews) Hotel
Breakfast • Free on-site parking • 2 swimming pools
Best Price Match Holiday Inn Express & Suites Chesapeake by IHG Best Price Match
7.3 (402 Reviews) Hotel
Breakfast • Free on-site parking • Indoor swimming pool
Best Price Match Hilton Norfolk The Main Best Price Match
8.6 (370 Reviews) Hotel
Breakfast • On-site parking • Indoor swimming pool
Best Price Match Quality Inn & Suites Olde Town Best Price Match
7.3 (402 Reviews) Hotel
Breakfast • Free on-site parking • Free WiFi
Best Price Match 
Fairfield Inn & Suites by Marriott Chesapeake Suffolk Best Price Match
7.6 (305 Reviews) Hotel
Breakfast • Free on-site parking • Free WiFi
Best Price Match 
Candlewood Suites Chesapeake-Suffolk by IHG Best Price Match
7.8 (139 Reviews) Hotel
Free on-site parking • Pet friendly • Private bathroom
Best Price Match 
Hampton Inn & Suites Chesapeake-Square Mall Best Price Match
6.9 (198 Reviews) Hotel
Breakfast • Free on-site parking • Free WiFi
Best Price Match Super 8 by Wyndham Portsmouth - Norfolk Best Price Match
4.0 (178 Reviews) Motel
On-site parking • Wifi • Private bathroom
Best Price Match About Chesapeake Vacation Rentals
Looking for places to stay in Chesapeake? Compare top options in Virginia.
With more than 25 Chesapeake vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Chesapeake.
Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Chesapeake. Prices average US $126 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Chesapeake, with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Stay Categories in Chesapeake
Use These Quick Filters to Find a Vacation Rental in Chesapeake
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Chesapeake.
Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Chesapeake. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.
Weather in Chesapeake
Average temperatures and rainfall by month range to help plan your stay in Chesapeake.
Mar - May
Avg High21°C / 69°F
Avg Low9°C / 48°F
Rainfall90 mm / 3.6 in
Jun - Aug
Avg High31°C / 88°F
Avg Low20°C / 68°F
Rainfall92 mm / 3.6 in
Sep - Nov
Avg High21°C / 71°F
Avg Low11°C / 52°F
Rainfall85 mm / 3.4 in
Dec - Feb
Avg High10°C / 50°F
Avg Low0°C / 33°F
Rainfall91 mm / 3.6 in