Chesapeake Bay Vacation Rentals

Compare 2,248 available properties from 24 providers
Chesapeake Bay
Save up to 17%

Best Vacation Home Deals in Chesapeake Bay

-15%
e.g. 11/2 - 11/9
Apartment ∙ 4 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $391 $460
travelstaytion
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-17%
e.g. 11/2 - 11/9
Apartment ∙ 8 guests ∙ 4 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $606 $732
travelstaytion
5.0
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-15%
e.g. 11/2 - 11/9
Apartment ∙ 4 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $391 $460
travelstaytion
5.0
View deal

Find a vacation rental that meets your criteria among the 2,248 welcoming accommodations from 24 partner websites in Chesapeake Bay. HomeToGo instantaneously presents you with the best offers by comparing all of the listed acommodations in Chesapeake Bay from 24 different providers.

Recommended Vacation Rentals in Chesapeake Bay

Rent a vacation accommodation in Chesapeake Bay: from $41 per night

House ∙ 3 guests ∙ 1 bedroom
Scotland, St. Inigoes, Maryland, United States
from $229
VRBO
4.9
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House ∙ 6 guests ∙ 3 bedrooms
Willoughby Spit, Norfolk, Virginia, United States
from $137
VRBO
4.4
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House ∙ 5 guests ∙ 1 bedroom
Port Republic, Solomons Island, Maryland, United States
from $108
VRBO
4.8
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Apartment ∙ 4 guests ∙ 2 bedrooms
Bay View, Norfolk, Virginia, United States
from $121
VRBO
4.2
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House ∙ 5 guests ∙ 2 bedrooms
Cape Charles, Northampton County, Virginia, United States
from $109
VRBO
4.7
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House ∙ 6 guests ∙ 2 bedrooms
Scotland, St. Inigoes, Maryland, United States
from $233
VRBO
4.8
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Apartment ∙ 6 guests ∙ 3 bedrooms
Chic's Beach, Virginia Beach, Virginia, United States
from $198
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Cape Charles, Northampton County, Virginia, United States
from $196
VRBO
4.4
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Apartment ∙ 2 guests ∙ 1 bedroom
Stevensville, Kent Island, Maryland, United States
from $161
VRBO
5.0
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Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 4 guests
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $41
VRBO
4.6
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Fishing
Apartment ∙ 5 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $41
VRBO
4.8
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Fishing
House ∙ 4 guests ∙ 2 bedrooms
Grimstead, Gwynn, Virginia, United States
from $194
VRBO
4.9
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Cape Charles, Northampton County, Virginia, United States
from $159
VRBO
4.4
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Fireplace
House ∙ 5 guests ∙ 2 bedrooms
Deal Island, Somerset County, Maryland, United States
from $135
VRBO
4.7
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Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Grimstead, Gwynn, Virginia, United States
from $125
VRBO
5.0
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Apartments With Balconies or Patios

Balcony/Patio
Apartment ∙ 4 guests
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from $145
VRBO
4.8
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Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Scotland, St. Inigoes, Maryland, United States
from $216
VRBO
4.8
View deal
Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Cobbs Creek, Piankatank, Virginia, United States
from $167
VRBO
4.9
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Popular Rental Amenities in Chesapeake Bay

  • Internet (2,034)
  • TV (1,980)
  • No smoking (1,978)
  • AC (1,964)
  • Kitchen (1,960)
  • Parking (1,834)
  • Microwave (1,829)
  • Washer (1,698)
  • Dishwasher (1,417)
  • Grill (1,354)
  • No pets (1,283)
  • Fishing (1,037)
Using our filters will help you find the perfect vacation rental in Chesapeake Bay. HomeToGo's data highlights that "internet" and "TVs" 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 42 properties including "saunas."

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 June (6/15 - 6/22) go up to $327 per night, which is the highest average price in the next 12 months. On average, the most interesting prices are in a week of March (3/2 - 3/9) 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 December (12/22 - 12/29). So far, 36% of the rentals are occupied this week. June (6/1 - 6/8) 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

The above is a climate diagram for Chesapeake Bay. During July, maximum temperatures go up to more than 87° However, temperatures can go lower than 28° in Chesapeake Bay in January. The rainiest month is July while the driest month is November.

Accommodations in Chesapeake Bay

1,492 out of the 2,248 listed properties in Chesapeake Bay are house rentals. They account for nearly half of the properties in this destination (48.28%). Additionally, these accommodations have an average size of 2,380 ft² as well as a median price of $487 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 749 properties to compare. These accommodations cost $150 per night on average and have an average size of 460 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 2,248 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 300 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 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