Chesapeake Beach Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake Beach

  • Modern Luxury Rental in North Beach!
     Home/Apartment
    HolidayLettings
    From
    $204
  • Panoramic Views of Herrington Harbour on the Bay.
     3br Home/Apartment
    HolidayLettings
    From
    $727
  • 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
    $186
  • Mermaid Cottage - Waterfront
     3br Home/Apartment
    Airbnb
    From
    $229
  • Wits End RV experience
     Home/Apartment
    Airbnb
    From
    $236
  • Bayside Cottage
    Excellent3br Home/Apartment
    Airbnb
    From
    $201
  • Southern Maryland Oasis
    ExcellentHome/Apartment
    Airbnb
    From
    $119

Check prices for these upcoming dates

Chesapeake Beach Vacation Rentals with a Pool

  • The Little Gypsy BoHome on the Bay!
    Excellent2br Home/Apartment
    Airbnb
    From
    $542
  • Gorgeous renovated 1bedroom apartment in Owings
    ExcellentHome/Apartment
    Airbnb
    From
    $124
  • Fossil Beach Paradise w/ Kayak, Bikes 1 hr from DC
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,067
  • Beach Home 1 hr from DC to Sail Pickleball & Kayak
     2br Home/Apartment
    Airbnb
    From
    $846

Chesapeake Beach Vacation Rentals with Wi-Fi

  • The Beach House
    Good4br Home/Apartment
    Airbnb
    From
    $565
  • Chesapeake Bay Beachfront Cottage, A Hidden Secret
    Excellent2br Home/Apartment
    Airbnb
    From
    $308
  • Hideaway on Chesapeake Bay
    ExcellentHome/Apartment
    Airbnb
    From
    $214
  • Charming Waterfront on Chesapeake Bay
    Excellent4br Home/Apartment
    Airbnb
    From
    $242

Chesapeake Beach Pet-Friendly Vacation Rentals

  • Hannahs Hideaway
    Excellent3br Home/Apartment
    Airbnb
    From
    $270
  • Rockhold Creek Cottage
    Excellent3br Home/Apartment
    Airbnb
    From
    $297
  • Sunrise @ Chesapeake
     3br Home/Apartment
    Airbnb
    From
    $346
  • Bayfields 9 Bed 3 Bath 27 Windows!
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,553

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
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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.

The Weather in Chesapeake Beach

Rainy days
95 º62
5
88 º40
4
78 º27
7
63 º28
5
61 º6
1
83 º19
6
78 º31
2
86 º37
3
90 º50
7
95 º59
3
96 º65
9
94 º61
8
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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.

What Expert Travelers Think

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    ArtMatters.InfoArtMatters.Info
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit

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