Ukraine Crisis Relief - Find and Offer Accommodation. Learn more
Choose the perfect vacation rental
Price per night
Revel in the laidback atmosphere of Chesapeake Bay vacation rentals
Chesapeake Bay, Maryland’s most famous estuary, is actually quite big – approximately 200 miles long. It is home to historical attractions such as Fort McHenry and Chesapeake Bay Maritime Museum, as well as natural attractions such as Blackwater National Wildlife Refuge and Calvert Cliffs.
Chesapeake Bay vacation homes are available in different types and sizes. From luxury townhouses and waterfront cottages to apartments and farmhouses, vacation rentals in Chesapeake Bay are available to suit your every need and desire.
Save up to 65%
Best Vacation Home Deals in Chesapeake Bay
Find a vacation rental that meets your criteria among the 10,842 welcoming accommodations from 11 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed accommodations in Chesapeake Bay from 11 different providers.
Book Vacation Rental Offers with the Highest User Rating
Top-Rated Rentals and Accommodations in Chesapeake Bay
Recommended Vacation Rentals in Chesapeake Bay
Find your perfect vacation rental in Chesapeake Bay: from $90 per night
Find Fantastic yet Inexpensive Offers
Budget-friendly Vacation Rentals in Chesapeake Bay
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Chesapeake Bay accommodation with high-speed internet.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Chesapeake Bay and book a vacation rental with air conditioning.
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Chesapeake Bay rental with full kitchen.
Popular Rental Amenities in Chesapeake Bay
Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "Internet" and "Air conditioning" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you enjoy soaking in the hot tub or you want to sweat it out in a sauna. There are just 232 listed accommodations providing "Hot tub" and 251 properties including "Sauna."
Price and Availability Index in Chesapeake Bay
Vacation Rental Price Information in Chesapeake Bay
The price graph will give you the nightly price average for the upcoming months of the year. Prices in a week of May (5/20 - 5/27) go up to $563 per night, which is the highest average price in the next 12 months. On average, the most interesting prices are in a week of December (12/2 - 12/9) as the average price is only $363 per night.
Rental Availability Information in Chesapeake Bay
Check out the graph above to find out how many accommodations are available in Chesapeake Bay(in %). More people travel to Chesapeake Bay a week in April (4/1 - 4/8). So far, 52% of the rentals are occupied this week. August (8/26 - 9/2) has got the highest percentage of available rentals.
The Weather in Chesapeake Bay
- Rainy days
The above is a climate diagram for Chesapeake Bay. During July, maximum temperatures go up to more than 88° However, temperatures can go lower than 28° in Chesapeake Bay in January. The rainiest month is January while the driest month is November.
7-Day Weather Forecast in Chesapeake Bay
Tue, 21 Mar
Wed, 22 Mar
Thu, 23 Mar
Fri, 24 Mar
Sat, 25 Mar
Sun, 26 Mar
Mon, 27 Mar
Receive exclusive offers, inspirational stories, and travel regulation updates.
Become a subscriber* and receive great tips on travel planning sent to your inbox!
Enter email address*
Accommodations for your vacation in Chesapeake Bay
3,490 out of the 10,842 listed properties in Chesapeake Bay are house rental. They account for many of the properties in this destination (60.28%). Additionally, these accommodations have an average size of 228 m² as well as a median price of $677 per night. Moreover, if you are going in a group of 8, house rental are the perfect accommodation type in Chesapeake Bay, as they usually welcome this exact group size. You can also search and find other accommodation types in Chesapeake Bay. Apartment rental are, for example, another popular accommodation option there with 858 properties to compare. These accommodations cost $304 per night on average and have an average size of 97 m².
What is the weather like in Chesapeake Bay?
Ideal time to visit Chesapeake Bay
The peak season for travelers to Chesapeake Bay is the summer period between June and August. Thousands of holidaymakers visit during this time for the hot weather and fun water-sports, including fishing, boating, and swimming.
If you specifically want to avoid the peak crowds, travel to Chesapeake Bay in either spring (March to May) or fall (September to November). During these seasons, you will be able to observe dolphins, explore salt marshes, and go hiking.
What are the best events and festivals in Chesapeake Bay?
Festivals in Chesapeake Bay
Chesapeake Bay Blues Festival is an annual event that takes place in Annapolis, Maryland. Spanning a weekend, this festival raises millions of dollars for charity. Attend this event and you can enjoy some of the world's best blues artists accompanied by gorgeous beachside views and amazing food.
Maryland Seafood Festival is held to celebrate the state's signature blue crabs. This festival also takes place in Annapolis and features numerous vendors selling crab cakes, steamed crab, and cream of crab soup, as well as braided crab pretzels.
What are the must-see attractions in Chesapeake Bay?
Iconic attractions in Chesapeake Bay
Chesapeake Bay Bridge-Tunnel
Located on US Route 13, Chesapeake Bay Bridge-Tunnel is a fixed link crossing in Virginia. This bridge-tunnel includes two mile-long tunnels and was opened in 1964. The structure is one of only ten bridge-tunnel constructions in the world.
Thomas Point Shoal Light
Thomas Point Shoal Light is the most popular lighthouse in Maryland. Built in 1825, it was listed on the National Register of Historic Places in 1975. It is open to the public for just 3 months in the year.
Susquehanna is the longest river in the continental US, and the Chesapeake Bay is actually the ria of this river. The Susquehanna River and the Chesapeake Bay are essentially part of one ecosystem.
Chesapeake Bay Bridge
Chesapeake Bay Bridge is an important link along US Routes 50 and 301. This bridge spans Chesapeake Bay in its entirety and connects the metropolitan Western Shore to the rural Eastern Shore in Maryland.
Situated at the base of Chesapeake Bay Bridge, Kent Island is home to beautiful views and numerous dining options. Kent Narrows is a small water channel that separates this island from the mainland.
Information about vacation rentals in Chesapeake Bay
🏡 Vacation rentals
💳 Possible discounts
up to 60%
🌙 Nightly prices starting at
⭐ Popular amenities
Internet, Air conditioning and TV
🐾 Pet friendly accommodations
🏊 Vacation rentals with pools
Frequently Asked Questions
What is the average price per night for a vacation home in Chesapeake Bay?
The price of a night's stay in Chesapeake Bay starts at $90. If you are looking for a house rental, the nightly price is $677 on average. A apartment rental Chesapeake Bay will cost $304 per night on average.
How many vacation rentals are available to book in Chesapeake Bay?
There are currently 10,842 rentals available for booking for your trip.
What amenities are most popular for vacation rentals in Chesapeake Bay?
Travelers look for Air conditioning, Internet, and TV when booking a vacation rental in Chesapeake Bay.
How many vacation rentals with a pool are in Chesapeake Bay?
There are 4,638 rentals across 11 providers in Chesapeake Bay.
Are dogs allowed in vacation rentals in Chesapeake Bay?
If traveling with a dog in Chesapeake Bay, 20% of vacation rentals allow pets.
What's the best time of year to travel to Chesapeake Bay?
Chesapeake Bay has its warmest time of year around July and June, with average nightly prices being around $90.
We list offers from thousands of providers, including: