Holiday rentals in Chesapeake Bay

Compare 6,827 available properties from 24 providers
Chesapeake Bay
Anytime
2 guests
Save up to 43%

Best holiday rental deals in Chesapeake Bay

-43%
Apartment ∙ 6 guests ∙ 3 bedrooms
Cape Charles, Northampton County, Virginia, United States
from £105 £184
HomeAway
5.0
View deal
-36%
House ∙ 6 guests ∙ 3 bedrooms
Deale, Anne Arundel County, Maryland, United States
from £119 £185
HomeAway
4.9
View deal
-17%
Apartment ∙ 6 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £205 £249
HomeAway
5.0
View deal

Browse 6,827 holiday rentals listed in Chesapeake Bay and discover the ideal home for a relaxing holiday. By directly analysing these different offers, HomeToGo features the most economical offers as well as the most popular lettings in Chesapeake Bay.

Recommended holiday lettings in Chesapeake Bay

Rent a holiday home, apartment or cottage in Chesapeake Bay from just £19 per night

House ∙ 3 guests ∙ 1 bedroom
Scotland, St. Inigoes, Maryland, United States
from £69
HomeAway
4.7
View deal
House ∙ 5 guests ∙ 3 bedrooms
Lake Shore, Anne Arundel County, Maryland, United States
from £146
HomeAway
4.9
View deal
House ∙ 2 guests ∙ 1 bedroom
Olde Huntersville, Norfolk, Virginia, United States
from £20
Airbnb
5.0
View deal
House ∙ 4 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £75
Airbnb
5.0
View deal
House ∙ 5 guests ∙ 2 bedrooms
Ingleside, Norfolk, Virginia, United States
from £40
Airbnb
5.0
View deal
House ∙ 5 guests ∙ 1 bedroom
Virginia Beach, Virginia, United States
from £35
Airbnb
5.0
View deal
House ∙ 3 guests ∙ 1 bedroom
Virginia Beach, Virginia, United States
from £57
Airbnb
5.0
View deal
House ∙ 6 guests ∙ 3 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £143
Airbnb
5.0
View deal
House ∙ 6 guests ∙ 3 bedrooms
Virginia Beach, Virginia, United States
from £65
Airbnb
5.0
View deal
See all offers

Best holiday lettings with a pool

Pool
House ∙ 5 guests ∙ 2 bedrooms
Saint Michaels, St. Michaels, Maryland, United States
from £164
HomeAway
4.8
View deal
Pool
House ∙ 7 guests ∙ 3 bedrooms
Cambridge, Dorchester County, Maryland, United States
from £381
HomeAway
4.8
View deal
Pool
House ∙ 2 guests ∙ 1 bedroom
Madison, Dorchester County, Maryland, United States
from £197
Airbnb
4.9
View deal
See all offers

Most popular holiday lettings with a fireplace

Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Rock Hall, Edesville, Maryland, United States
from £390
HomeAway
4.9
View deal
Fireplace
House ∙ 2 guests ∙ 1 bedroom
Stevensville, Kent Island, Maryland, United States
from £65
Airbnb
5.0
View deal
Fireplace
House ∙ 2 guests ∙ 1 bedroom
Stevensville, Kent Island, Maryland, United States
from £43
Airbnb
5.0
View deal
See all offers

Recommended pet-friendly holiday lettings

Pet-friendly
Apartment ∙ 5 guests ∙ 2 bedrooms
Annapolis, Anne Arundel County, Maryland, United States
from £134
HomeAway
5.0
View deal
Pet-friendly
House ∙ 5 guests ∙ 2 bedrooms
Deal Island, Somerset County, Maryland, United States
from £98
HomeAway
4.7
View deal
Pet-friendly
Apartment ∙ 6 guests ∙ 2 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £179
HomeAway
4.8
View deal
See all offers

Popular holiday rental amenities in Chesapeake Bay

  • Kitchen (6,508)
  • Internet (6,284)
  • TV (5,937)
  • Washer (5,191)
  • AC (5,139)
  • No smoking (3,561)
  • Microwave (3,277)
  • Pool (2,636)
  • Dishwasher (2,383)
  • BBQ (2,338)
  • Parking (1,925)
  • Garden (1,811)

Price and Availability Index in Chesapeake Bay

Holiday Letting Price Information in Chesapeake Bay

In the above graph, you will find Chesapeake Bay is most expensive in June (15/06 - 22/06), when prices are on average £239 a night. The week with the lowest average prices is in March (02/03 - 09/03).

Holiday Home Availability Information in Chesapeake Bay

Check out the graph above to find out how many holiday rentals are available in Chesapeake Bay (in %). More people travel to Chesapeake Bay during a week in February (08/02 - 15/02). So far, 34% of the Chesapeake Bay holiday lettings are occupied this week. The week with the highest percentage of available lettings is in August (24/08 - 31/08).

The Weather in Chesapeake Bay

6°
-2°
7°
-1°
13°
3°
19°
8°
24°
15°
29°
19°
31°
22°
29°
20°
26°
17°
20°
11°
14°
5°
12°
3°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Chesapeake Bay. July is the warmest month of the year in Chesapeake Bay, with temperatures reaching an average daily maximum of 31°. However, temperatures can go lower than -2° in Chesapeake Bay in January. The rainiest month is July, while the driest month is November.

Accommodation options in Chesapeake Bay

Nearly half of the accommodation options (40.12%) in Chesapeake Bay are house rentals. They are the most typical holiday lettings there. These properties have a median size of 211 m² as well as an average price of £277 per night. Furthermore, these properties are usually perfect if you're going in a group of 7, as that is the average number of people that house rentals are able to host in Chesapeake Bay. Apartment rentals are the other most frequently offered property type in Chesapeake Bay. These properties cost £189 per night, on average, and have an average size of 110 m².

Revel in the laidback atmosphere of Chesapeake Bay holiday lettings

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 holiday homes are available in different types and sizes. From luxury townhouses and waterfront cottages to apartments and farmhouses, holiday lettings in Chesapeake Bay are available to suit your every need and desire.

Show all 6,827 properties
Weather & Climate

Ideal time to visit Chesapeake Bay

The peak season for travellers 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 600 providers, including:

Booking.com Holiday Rentals in Chesapeake Bay Novasol Holiday Rentals in Chesapeake Bay TripAdvisor Holiday Rentals in Chesapeake Bay Inter Chalet Holiday Rentals in Chesapeake Bay HomeAway Holiday Rentals in Chesapeake Bay EveryStay Holiday Rentals in Chesapeake Bay Interhome Holiday Rentals in Chesapeake Bay 9flats.com Holiday Rentals in Chesapeake Bay HouseTrip Holiday Rentals in Chesapeake Bay Belvilla Holiday Rentals in Chesapeake Bay Sykes Cottages Holiday Rentals in Chesapeake Bay Homestay.com Holiday Rentals in Chesapeake Bay Ski Planet Holiday Rentals in Chesapeake Bay Only-apartments Holiday Rentals in Chesapeake Bay James Villa Holidays Holiday Rentals in Chesapeake Bay