Chesapeake Beach Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake Beach

Seahorse Guest Cottage near the Bay, dog friendly
Good1br Cottage
HolidayLettingsFrom $251
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Renovated Luxury Waterview House
3br Home/Apartment
HolidayLettingsFrom $460
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Panoramic Views of Herrington Harbour on the Bay.
3br Home/Apartment
HolidayLettingsFrom $727
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Wits End RV experience
1br Home/Apartment
AirbnbFrom $234
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Beautiful townhouse and community
3br Home/Apartment
AirbnbFrom $179
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Indoor pool/spa nestled in Southern Md. woods.
3br Home/Apartment
AirbnbFrom $583
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@THEDRIFTWOODLODGE !!!JUL.19-21 NOW OPEN!!!
Excellent6br Home/Apartment
AirbnbFrom $918
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Big House on the Bay w/beach sleeps 16+ *c special
Excellent6br Home/Apartment
AirbnbFrom $945
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Chesapeake Beach Vacation Rentals with a Pool

Slumber Soundly On Superb Sailboat
Excellent1br Home/Apartment
AirbnbFrom $107
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Girls Beach Apt w/Sailing, Pickleball, Pool, Kayak
2br Home/Apartment
AirbnbFrom $809
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Scientists Cliffs Fossil Beach House Sleeps 12
4br Home/Apartment
AirbnbFrom $1205
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Luxury FOSSIL BEACH Apt w Pickleball, Kayak, Pool
2br Home/Apartment
AirbnbFrom $593
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Chesapeake Beach Vacation Rentals with Wi-Fi

Charming Waterfront on Chesapeake Bay
Excellent4br Home/Apartment
AirbnbFrom $358
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Great Bayside Getaway 35 min from DC and Annapolis
Excellent3br Other
AirbnbFrom $308
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Waterfront Chalet
Good3br Chalet
AirbnbFrom $322
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Gorgeous water view studio!
ExcellentHome/Apartment
AirbnbFrom $169
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Chesapeake Beach Pet-Friendly Vacation Rentals

Sunrise @ Chesapeake
3br Home/Apartment
AirbnbFrom $385
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Fossil Beach Paradise w Pool for 4
Excellent2br Home/Apartment
AirbnbFrom $802
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"Suite" Herring Bay Views
Excellent1br Other
AirbnbFrom $207
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Beach Apt Fossils,Pickleball, Kayak,Bikes Sleeps 6
Good2br Bedroom
AirbnbFrom $345
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Chesapeake Beach Travel Guide

People come to Chesapeake Beach, Maryland for its historic, seaside atmosphere, relaxing, pretty beach and other fun attractions like the Chesapeake Beach Railway Museum and the Chesapeake Beach Water Park.

Things to Do in Chesapeake Beach

On the actual bay you can enjoy the beautiful views and wander the marina, the boardwalk, or spend the day at the beach. Back in the day this was quite the resort with arcade games and all the traditional amusements.

Top attractions in town include the Railway Museum for exhibits on history, steamboats and trains and also Maryland's only surfing museum and surf art gallery.

The water park is a fun splash-filled place for the family to enjoy, with slides and various pools.

Best Time to Visit Chesapeake Beach

Visit Chesapeake Beach in summer for beach days and sunbathing, or off season to explore it at a less crowded time.

Price and Availability in Chesapeake Beach

Most expensive

Most availability

The most expensive month to stay in a vacation rental in Chesapeake Beach is in June, while the cheapest month is in March. The most popular time to book a vacation rental in Chesapeake Beach is in the high season in July. Chesapeake Beach has its low season in December, when less people are visiting and the vacation home occupancy rate drops.

The cheapest day to stay at a vacation rental in Chesapeake Beach tends to be Thursday, while the most expensive day tends to be Saturday. Vacation homes in Chesapeake Beach tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Chesapeake Beach

SEE FULL WEATHER FORECAST:

96º 65º

8.8

94º 61º

7.64

95º 62º

4.93

88º 40º

3.81

78º 27º

7.33

63º 28º

5.35

61º 6º

1.36

83º 19º

5.7

78º 31º

2.42

86º 37º

3.28

90º 50º

7.45

95º 59º

3.37

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Rainy days