Chesapeake Bay, Maryland, United States
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Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Weather in Chesapeake Bay

Hi: 8.9°
Lo: -0.6°
January
Hi: 10.6°
Lo: 0.6°
February
Hi: 14.4°
Lo: 3.9°
March
Hi: 20°
Lo: 8.9°
April
Hi: 23.9°
Lo: 13.9°
May
Hi: 28.3°
Lo: 19.4°
June
Hi: 30.6°
Lo: 21.7°
July
Hi: 29.4°
Lo: 21.1°
August
Hi: 26.1°
Lo: 17.8°
September
Hi: 21.1°
Lo: 11.1°
October
Hi: 16.1°
Lo: 6.1°
November
Hi: 11.1°
Lo: 1.7°
December

Vacation Rentals in Chesapeake Bay

Find the best Chesapeake Bay vacation rentals on Tripping.com. With over 24285 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Chesapeake Bay range from $25 a night. Many rentals can also be booked directly online.

Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 20680 homes in Chesapeake Bay offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 9077 rentals with pool or jacuzzi, or relax with the family in one of the 21152 homes with cable TV.

For all those pet owners with dogs or cats, Chesapeake Bay offers 3699 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com.

Search properties from 14 vacation rental sites in Chesapeake Bay where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 11815 HomeAway rentals, 5595 TripAdvisor short term rentals and 2206 Booking.com vacation rentals.