Chesapeake Beach Vacation Rentals

Our Favorite Vacation Rentals in Chesapeake Beach

  • Modern Luxury Rental in North Beach!
     Home/Apartment
    HolidayLettings
    From
    $234
  • Panoramic Views of Herrington Harbour on the Bay.
     3br Home/Apartment
    HolidayLettings
    From
    $813
  • Indoor pool and spa located in beautiful Southern Maryland woodlands
     3br Home/Apartment
    HolidayLettings
    From
    $618
  • CUTE CHESAPEAKE BEACH COTTAGE CLOSE TO THE BAY
    ExcellentHome/Apartment
    Airbnb
    From
    $105
  • Bayside Cottage
    Excellent3br Home/Apartment
    Airbnb
    From
    $212
  • Floor-to-Ceiling Views of the Chesapeake Bay +Dock
    Excellent4br Home/Apartment
    Airbnb
    From
    $339
  • The Beach House
    Good4br Home/Apartment
    Airbnb
    From
    $588
  • Chesapeake Bay Beachfront Cottage, A Hidden Secret
    Excellent2br Home/Apartment
    Airbnb
    From
    $280

Check prices for these upcoming dates

Chesapeake Beach Vacation Rentals with a Pool

  • The Little Gypsy BoHome on the Bay!
    Excellent3br Home/Apartment
    Airbnb
    From
    $429
  • Gorgeous renovated 1bedroom apartment in Owings
    ExcellentHome/Apartment
    Airbnb
    From
    $207
  • Fossil Beach Paradise w/ Kayak, Bikes 1 hr from DC
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,290
  • Bayfields 9 Bed 3 Bath 27 Windows!
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,666

Chesapeake Beach Vacation Rentals with Wi-Fi

  • Bay Breeze Lodge
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,220
  • Hideaway on Chesapeake Bay
    ExcellentHome/Apartment
    Airbnb
    From
    $180
  • Chesapeake Bay Apartment for all Seasons
    Excellent3br Home/Apartment
    Airbnb
    From
    $143
  • Hannahs Hideaway
    Excellent3br Home/Apartment
    Airbnb
    From
    $213

Chesapeake Beach Pet-Friendly Vacation Rentals

  • Wonderful West Shore Waterfront Cottage (Near DC)
    Excellent3br Home/Apartment
    Airbnb
    From
    $259
  • Rockhold Creek Cottage
    Excellent3br Home/Apartment
    Airbnb
    From
    $297
  • Wits End RV experience
     Home/Apartment
    Airbnb
    From
    $236
  • Cozy North Beach Eco-Conscious Beach House
     2br Home/Apartment
    Airbnb
    From
    $153

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
68° 12°
3
68° 16°
2
80° 24°
3
85° 37°
2
94° 51°
6
98° 58°
2
101° 70°
4
96° 66°
2
96° 57°
0
94° 44°
4
65° 26°
1
60° 22°
2
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
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 101 ˚F. The coolest month is December, when temperatures drop to 12 ˚F. The wettest month in Chesapeake Beach is August with 5.97 inches of rain, while the driest month is April with 0.25 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — 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

Destinations near Chesapeake Beach

  • Ocean City6,339 Properties
  • Oakland2,283 Properties
  • McHenry1,768 Properties
  • Swanton1,399 Properties
  • Annapolis1,190 Properties
  • Baltimore1,138 Properties
  • Bethesda587 Properties
  • Ocean Pines466 Properties
  • Silver Spring441 Properties
  • Frederick402 Properties
  • Cambridge370 Properties
  • Rockville338 Properties
  • Berlin335 Properties
  • Gaithersburg305 Properties
  • Oxon Hill293 Properties
  • Laurel283 Properties
  • Columbia274 Properties
  • Salisbury254 Properties
  • Hanover234 Properties
  • Aberdeen201 Properties
  • Fort Washington193 Properties
  • Easton187 Properties
  • Takoma Park185 Properties
  • Stevensville168 Properties
  • Hyattsville154 Properties
  • Chestertown147 Properties
  • College Park90 Properties
  • St. Michaels81 Properties
  • North Beach57 Properties
  • Mount Rainier52 Properties
  • Accokeek45 Properties
  • Lusby40 Properties
  • West Ocean City18 Properties
  • Emmitsburg10 Properties