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Chesapeake Beach Vacation Rentals

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Our Favorite Vacation Rentals in Chesapeake Beach

  • Seahorse Guest Cottage near the Bay, dog friendly
    Seahorse Guest Cottage near the Bay, dog friendly
    Good
    HolidayLettingsFrom $251
    View Deal
  • Panoramic Views of Herrington Harbour on the Bay.
    Panoramic Views of Herrington Harbour on the Bay.
     
    HolidayLettingsFrom $727
    View Deal
  • WELCOME TO TIDE’S END. 2 BLOCKS AWAY TO THE BAY.
    WELCOME TO TIDE’S END. 2 BLOCKS AWAY TO THE BAY.
    Excellent
    AirbnbFrom $227
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  • Full house rental in Twin Beach. 1 bk from the Bay
    Full house rental in Twin Beach. 1 bk from the Bay
    Excellent
    AirbnbFrom $123
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  • Southern Maryland Oasis
    Southern Maryland Oasis
     
    AirbnbFrom $118
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  • THE DRIFTWOOD LODGE - WATERFRONT CHESAPEAKE BAY
    THE DRIFTWOOD LODGE - WATERFRONT CHESAPEAKE BAY
    Excellent
    AirbnbFrom $1219
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  • Fossil Hunters Haven
    Fossil Hunters Haven
    Excellent
    AirbnbFrom $115
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  • Big House on the Bay w/beach sleeps 16+ *c special
    Big House on the Bay w/beach sleeps 16+ *c special
    Excellent
    AirbnbFrom $945
    View Deal
See all 37 deals in Chesapeake Beach

Chesapeake Beach Vacation Rentals with a Pool

  • Sportlovers Beach Apt for 4 w Fossils, Pool, Kayak
    Sportlovers Beach Apt for 4 w Fossils, Pool, Kayak
     
    AirbnbFrom $755
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  • FOSSIL BEACH Apt w Pickleball courts, fireplace
    FOSSIL BEACH Apt w Pickleball courts, fireplace
     
    AirbnbFrom $593
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  • Peaceful Romantic Sailing Paradise w/ Boat & Crew
    Peaceful Romantic Sailing Paradise w/ Boat & Crew
     
    AirbnbFrom $444
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See all deals in Chesapeake Beach with a pool

Chesapeake Beach Vacation Rentals with Wi-Fi

  • Hideaway on Chesapeake Bay
    Hideaway on Chesapeake Bay
    Excellent
    AirbnbFrom $212
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  • Charming Waterfront on Chesapeake Bay
    Charming Waterfront on Chesapeake Bay
    Excellent
    AirbnbFrom $358
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  • Lovely Chesapeake Waterfront Flat Just 26 Mi to DC
    Lovely Chesapeake Waterfront Flat Just 26 Mi to DC
    Excellent
    AirbnbFrom $186
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  • Waterfront Chalet
    Waterfront Chalet
    Good
    AirbnbFrom $322
    View Deal
See all deals in Chesapeake Beach with WiFis

Chesapeake Beach Pet-Friendly Vacation Rentals

  • Hannahs hideaway
    Hannahs hideaway
     
    AirbnbFrom $267
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  • Rockhold Creek Cottage
    Rockhold Creek Cottage
    Excellent
    AirbnbFrom $294
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  • Apt w Fossil Beach, Tennis, Pool, Trails, Kayak
    Apt w Fossil Beach, Tennis, Pool, Trails, Kayak
    Excellent
    AirbnbFrom $802
    View Deal
  • Bayfields 9 Bed 3 Bath 27 Windows!
    Bayfields 9 Bed 3 Bath 27 Windows!
    Excellent
    AirbnbFrom $1456
    View Deal
See all deals in Chesapeake Beach that allow pets

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
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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

90º 50º
7.45
95º 59º
3.37
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
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
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 January, when temperatures drop to 6 ˚F. The wettest month in Chesapeake Beach is July with 8.8 inches of rain, while the driest month is January with 1.36 inches of rain.

What Expert Travelers Think

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