Holiday rentals in Chesapeake Bay

Compare 3,082 available properties from 24 providers
Chesapeake Bay
Save up to 35%

Best holiday rental deals in Chesapeake Bay

-18%
e.g. 5/01 - 12/01
House ∙ 5 guests ∙ 1 bedroom
Port Republic, Solomons Island, Maryland, United States
from £125 £153
HomeAway
4.8
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-31%
e.g. 27/10 - 3/11
House ∙ 6 guests ∙ 2 bedrooms
East Ocean View, Norfolk, Virginia, United States
from £177 £256
HomeAway
4.4
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-35%
e.g. 1/12 - 8/12
House ∙ 6 guests ∙ 2 bedrooms
Scotland, St. Inigoes, Maryland, United States
from £156 £240
HomeAway
4.8
View deal

3,082 welcoming holiday rentals from 24 holiday letting websites are listed in Chesapeake Bay with prices beginning at £34 per night. By directly analysing these holiday rentals, HomeToGo highlights the most economical offers and the highest rated properties in Chesapeake Bay.

Recommended holiday lettings in Chesapeake Bay

Rent a holiday apartment, home or cottage in Chesapeake Bay: from £34 per night

House ∙ 3 guests ∙ 1 bedroom
Scotland, St. Inigoes, Maryland, United States
from £69
HomeAway
4.9
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House ∙ 3 guests ∙ 1 bedroom
Scotland, St. Inigoes, Maryland, United States
from £81
HomeAway
4.7
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Apartment ∙ 6 guests ∙ 3 bedrooms
Chic's Beach, Virginia Beach, Virginia, United States
from £227
HomeAway
4.9
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House ∙ 4 guests ∙ 2 bedrooms
Wittman, Bay Hundred, Maryland, United States
from £188
HomeAway
4.6
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House ∙ 5 guests ∙ 2 bedrooms
Cape Charles, Northampton County, Virginia, United States
from £79
HomeAway
4.7
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House ∙ 6 guests ∙ 3 bedrooms
Wittman, Bay Hundred, Maryland, United States
from £214
HomeAway
4.9
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Apartment ∙ 4 guests ∙ 1 bedroom
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £113
HomeAway
4.4
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House ∙ 6 guests ∙ 3 bedrooms
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £163
HomeAway
5.0
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Top holiday accommodation with fishing spots nearby

Fishing
House ∙ 4 guests ∙ 2 bedrooms
Scotland, St. Inigoes, Maryland, United States
from £99
HomeAway
4.8
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Fishing
House ∙ 6 guests ∙ 3 bedrooms
Scotland, St. Inigoes, Maryland, United States
from £97
HomeAway
5.0
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Fishing
House ∙ 4 guests ∙ 2 bedrooms
Grimstead, Gwynn, Virginia, United States
from £130
HomeAway
4.8
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Fishing
House ∙ 5 guests ∙ 1 bedroom
Port Republic, Solomons Island, Maryland, United States
from £125
HomeAway
4.8
View deal
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Best holiday homes with a patio or terrace

Balcony/Patio
Apartment ∙ 4 guests
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £114
HomeAway
4.8
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Balcony/Patio
Apartment ∙ 2 guests
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £98
HomeAway
4.7
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Balcony/Patio
House ∙ 2 guests ∙ 1 bedroom
Northeast Virginia Beach, Virginia Beach, Virginia, United States
from £110
HomeAway
5.0
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Balcony/Patio
House ∙ 6 guests ∙ 2 bedrooms
East Ocean View, Norfolk, Virginia, United States
from £138
HomeAway
4.4
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Most popular holiday cottages with a fireplace

Fireplace
House ∙ 5 guests ∙ 2 bedrooms
Deal Island, Somerset County, Maryland, United States
from £109
HomeAway
4.7
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Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Scotland, St. Inigoes, Maryland, United States
from £156
HomeAway
4.8
View deal
Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Irvington, Lancaster County, Virginia, United States
from £121
HomeAway
5.0
View deal
Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Irvington, Lancaster County, Virginia, United States
from £97
HomeAway
4.8
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Popular holiday rental amenities in Chesapeake Bay

  • Internet (2,265)
  • TV (2,186)
  • AC (2,182)
  • No smoking (2,158)
  • Kitchen (2,129)
  • Parking (2,086)
  • Microwave (1,982)
  • Washer (1,711)
  • Dishwasher (1,558)
  • BBQ (1,416)
  • No pets (1,261)
  • Fishing (1,194)
Finding a rental that includes a pool shouldn't be too difficult in Chesapeake Bay. One-third of the holiday lettings include one. In addition, more House rentals have pools than any other accommodation type. They are a great choice if you go in a group of 4, as that is the number of people they can usually accommodate. Among these holiday rentals, nearly half of them are within 2 kilometres of water. Travellers who are specifically searching for a pet-friendly accommodation will find Chesapeake Bay suitable, as many lettings are pet-friendly. House rentals are the most pet-friendly type of accommodation in Chesapeake Bay. In addition, a night in a pet-friendly accommodation there is, on average, £286. You can also find suitable city properties, as a few of the pet-friendly rentals are centrally located (less than 2 kilometres from the city centre).

Price and Availability Index Chesapeake Bay

Holiday Letting Price Information in Chesapeake Bay

In the above graph, you will find information on average prices of the holiday lettings & cottages in Chesapeake Bay. Chesapeake Bay is more expensive in August (25/08 - 01/09), where prices are on average £273 a night. The week with the lowest average prices is in November (24/11 - 01/12).

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 a week in August (25/08 - 01/09). So far, 45% of the rentals are occupied this week. The week with the highest percentage of available lettings is in May (11/05 - 18/05).

The weather in Chesapeake Bay


-2°

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

The above is a climate diagram for Chesapeake Bay. On average, the warmest month is July. However, temperatures can go lower than -2° in Chesapeake Bay in January. It may rain 13 days in January while it typically rains only 9 days in November.

More than half of the accommodation options (50.76%) in Chesapeake Bay are house rentals. They are the most common properties on offer there. Additionally, the median nightly price of house rentals there is £348, and the average size is 224 m². Moreover, these holiday properties tend to be great for large groups, since most can welcome 9 holidaymakers. If you would prefer to book another holiday property type, you may want to check out apartment rentals, which are the other most frequent property type in Chesapeake Bay. Apartment rentals in Chesapeake Bay are 104 m² on average, with an average price of £224 a night.

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.

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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 300 providers, including:

Booking.com Holiday Rentals in Chesapeake Bay Wimdu 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