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Chesapeake Beach Vacation Rentals

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Our Favorite Vacation Rentals in Chesapeake Beach

  • Panoramic Views of Herrington Harbour on the Bay.
     3br Home/Apartment
    HolidayLettings
    From
    $770
  • Indoor pool and spa located in beautiful Southern Maryland woodlands
     3br Home/Apartment
    HolidayLettings
    From
    $618
  • Chesapeake Beach Apt. Walk to Bay, Beach & Marina!
     Home/Apartment
    HolidayLettings
    From
    $162
  • WELCOME TO TIDE’S END. 2 BLOCKS AWAY TO THE BAY.
    Excellent4br Home/Apartment
    Airbnb
    From
    $211
  • Mermaid Cottage - Waterfront
     3br Home/Apartment
    Airbnb
    From
    $256
  • Full house rental in Twin Beach. 1 bk from the Bay
    Excellent2br Home/Apartment
    Airbnb
    From
    $136
  • Bayside Cottage
    Excellent3br Home/Apartment
    Airbnb
    From
    $212
  • Waterfront Cottage Near Herrington and North Beach
    Excellent2br Home/Apartment
    Airbnb
    From
    $240
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Check prices for these upcoming dates

Chesapeake Beach Vacation Rentals with a Pool

  • Gorgeous renovated 1bedroom apartment in Owings
    ExcellentHome/Apartment
    Airbnb
    From
    $177
  • Fossil Beach Paradise w/ Kayak, Bikes 1 hr from DC
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,235
  • Luxury Home Sleeps 18, Private Pool, Close to DC
    Excellent6br Home/Apartment
    Airbnb
    From
    $959
  • Bayfields 9 Bed 3 Bath 27 Windows!
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,609
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Chesapeake Beach Vacation Rentals with Wi-Fi

  • Southern Maryland Oasis
    ExcellentHome/Apartment
    Airbnb
    From
    $119
  • The Beach House
    Good4br Home/Apartment
    Airbnb
    From
    $565
  • Chesapeake Bay Beachfront Cottage, A Hidden Secret
    Excellent2br Home/Apartment
    Airbnb
    From
    $209
  • The Driftwood Lodge - Waterfront Chesapeake Bay
    Excellent6br Home/Apartment
    Airbnb
    From
    $707
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Chesapeake Beach Pet-Friendly Vacation Rentals

  • The Deale Delight
    Excellent3br Home/Apartment
    Airbnb
    From
    $212
  • Hannahs Hideaway
    Excellent3br Home/Apartment
    Airbnb
    From
    $204
  • Waterfront Relax, Bond, Play Cottage on Chesapeake
    Excellent3br Home/Apartment
    Airbnb
    From
    $255
  • Sunrise @ Chesapeake
     3br Home/Apartment
    Airbnb
    From
    $346
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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.

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Price and Availability in Chesapeake Beach

Most expensive
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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 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.
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The Weather in Chesapeake Beach

Rainy days
78° 27°
7
63° 28°
5
61° 6°
1
83° 19°
6
78° 31°
2
86° 37°
3
90° 50°
7
95° 59°
3
96° 65°
9
94° 61°
8
95° 62°
5
88° 40°
4
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Chesapeake Beach. The warmest months in Chesapeake Beach are June and July, when temperatures reach 96 ˚F. The coolest month is December, when temperatures drop to 6 ˚F. The wettest month in Chesapeake Beach is June with 8.8 inches of rain, while the driest month is December with 1.36 inches of rain.

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    Jeff CampbellMiddle Class Dad
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