Chesapeake Bay Vacation Rentals

Compare 2,499 available properties from 18 providers
Chesapeake Bay
Save up to 28%

Best vacation home deals in Chesapeake Bay

$313
from $236
-25%
1100 ft² House
6 2
Chesapeake Beach, Sunderland, Maryland, United States
Found on
HomeAway
$625
from $506
-19%
1820 ft² House
6 3
Annapolis, Anne Arundel County, Maryland, United States
Found on
HomeAway
$215
from $154
-28%
Apartment
4 1
Naval Academy, Annapolis, Maryland, United States
Found on
HomeAway

Find a vacation rental that meets your criteria among the 2,499 welcoming accommodations from 18 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed acommodations in Chesapeake Bay from 18 different providers.

Recommended vacation rentals in Chesapeake Bay

Rent a vacation accommodation in Chesapeake Bay: from $43 per night

from $88
440 ft² House
3 1
St. Inigoes, St. Mary's County, Maryland, United States
4.8
"Excellent" 56 reviews
Found on HomeAway
from $112
800 ft² Apartment
4 2
Bay View, Norfolk, Virginia, United States
5.0
"Excellent" 1 review
Found on VRBO
from $134
1000 ft² House
6 2
Northeast Virginia Beach, Virginia Beach, Virginia, United States
4.5
"Excellent" 18 reviews
Found on VRBO
from $111
810 ft² Apartment
4 2
Bay View, Norfolk, Virginia, United States
4.3
"Outstanding" 4 reviews
Found on VRBO
from $103
470 ft² House
3 1
St. Inigoes, St. Mary's County, Maryland, United States
4.7
"Excellent" 53 reviews
Found on HomeAway
from $288
1700 ft² Apartment
6 3
Chic's Beach, Virginia Beach, Virginia, United States
4.9
"Excellent" 35 reviews
Found on VRBO
from $146
House
5 2
Cape Charles, Northampton County, Virginia, United States
4.6
"Excellent" 34 reviews
Found on VRBO
from $65
House
4
Northeast Virginia Beach, Virginia Beach, Virginia, United States
4.5
"Excellent" 514 reviews
Found on EconoLodge
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  Vacation homes with fishing spots nearby

from $154
500 ft² House
2 1
Virginia, United States
5.0
"Excellent" 21 reviews
Found on VRBO
from $145
360 ft² Apartment
4
Northeast Virginia Beach, Virginia Beach, Virginia, United States
4.7
"Excellent" 6 reviews
Found on VRBO
from $142
290 ft² Apartment
2
Northeast Virginia Beach, Virginia Beach, Virginia, United States
4.5
"Excellent" 6 reviews
Found on VRBO
from $126
500 ft² House
4 2
St. Inigoes, St. Mary's County, Maryland, United States
4.8
"Excellent" 50 reviews
Found on HomeAway
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  Vacation rentals with a fireplace

from $138
House
5 2
Deal Island, Somerset County, Maryland, United States
4.8
"Excellent" 57 reviews
Found on HomeAway
from $161
1290 ft² House
5 1
Solomons Island, Calvert County, Maryland, United States
4.8
"Excellent" 26 reviews
Found on HomeAway
from $272
1290 ft² House
6 2
St. Inigoes, St. Mary's County, Maryland, United States
4.8
"Excellent" 42 reviews
Found on HomeAway
from $103
1290 ft² House
6 3
St. Inigoes, St. Mary's County, Maryland, United States
5.0
"Excellent" 11 reviews
Found on HomeAway
See all offers

  Apartments with a balcony or patio

from $154
440 ft² Apartment
3
Northeast Virginia Beach, Virginia Beach, Virginia, United States
4.8
"Excellent" 47 reviews
Found on VRBO
from $261
1290 ft² House
4 2
Northeast Virginia Beach, Virginia Beach, Virginia, United States
4.9
"Excellent" 19 reviews
Found on VRBO
from $240
1290 ft² House
4 2
Northeast Virginia Beach, Virginia Beach, Virginia, United States
5.0
"Excellent" 1 review
Found on VRBO
from $175
1800 ft² House
6 2
East Ocean View, Norfolk, Virginia, United States
4.4
"Outstanding" 39 reviews
Found on VRBO
See all offers

Popular rental amenities in Chesapeake Bay

  • Kitchen (1,924)
  • Internet (1,821)
  • TV (1,815)
  • AC (1,767)
  • No smoking (1,734)
  • Microwave (1,732)
  • Parking (1,659)
  • Washer (1,407)
  • Dishwasher (1,376)
  • Grill (1,220)
  • No pets (1,177)
  • Fishing (1,079)
Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "TVs" and "internet" turn out to be the most frequently offered features in Chesapeake Bay. Plan your vacation in advance if you need a crib for your baby or you want to sweat it out in a sauna. There are just 1 listed accommodations providing "cribs" and 43 properties including "saunas."

Price and Availability Index Chesapeake Bay

Vacation Rental Price Information in Chesapeake Bay

The price graph will give you the nightly price average for the upcoming 6 months. Prices in a week of June (6/16 - 6/23) go up to $356 per night, which is the highest average price in the next 6 months. On average, the most interesting prices are in a week of October (10/27 - 11/3) as the average price is only $275 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 June (6/30 - 7/7). So far, 57% of the rentals are occupied this week. October (10/27 - 11/3) has got the highest percentage of available rentals.

The weather in Chesapeake Bay

43°
28°
45°
30°
55°
37°
66°
46°
75°
59°
84°
66°
88°
72°
84°
68°
79°
63°
68°
52°
57°
41°
54°
37°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. On average, the warmest month is July. January is the coolest month, with average minimal temperature reaching 28°. January is the wettest month.

1,537 out of the 2,499 listed properties in Chesapeake Bay are house rentals. They account for more than half of the properties in this destination (50.26%). Additionally, these accommodations have an average size of 2,450 ft² as well as a median price of $431 per night. Moreover, if you are going in a group of 9, house rentals 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. Hotel rooms are, for example, another popular accommodation option there with 812 properties to compare. These accommodations cost $239 per night on average and have an average size of 550 ft².

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.

Show all 2,499 properties
Weather & Climate

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.

Local Events

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.

Sights & things to do 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

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.

Kent Island

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.

We compare more than 250 providers, including:

Booking.com Vacation Rentals in Chesapeake Bay VRBO Vacation Rentals in Chesapeake Bay HomeAway Vacation Rentals in Chesapeake Bay TripAdvisor Vacation Rentals in Chesapeake Bay VacationRentals.com Vacation Rentals in Chesapeake Bay HouseTrip Vacation Rentals in Chesapeake Bay FlipKey Vacation Rentals in Chesapeake Bay Wimdu Vacation Rentals in Chesapeake Bay 9flats.com Vacation Rentals in Chesapeake Bay VaycayHero Vacation Rentals in Chesapeake Bay PerfectPlaces.com Vacation Rentals in Chesapeake Bay Homestay.com Vacation Rentals in Chesapeake Bay only-apartments Vacation Rentals in Chesapeake Bay Interhome Vacation Rentals in Chesapeake Bay Bedycasa Vacation Rentals in Chesapeake Bay Novasol Vacation Rentals in Chesapeake Bay HomeEscape Vacation Rentals in Chesapeake Bay