Chesapeake Beach Vacation Rentals

Check prices for these upcoming dates

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
94° 44°
4
65° 26°
1
60° 22°
2
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
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Chesapeake Beach. The hottest month in Chesapeake Beach is June, when temperatures peak at 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

  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

Destinations near Chesapeake Beach

  • Ocean City6,728 Properties
  • Oakland2,350 Properties
  • McHenry1,828 Properties
  • Swanton1,432 Properties
  • Annapolis1,376 Properties
  • Baltimore1,150 Properties
  • Bethesda622 Properties
  • Ocean Pines494 Properties
  • Silver Spring481 Properties
  • Frederick421 Properties
  • Cambridge389 Properties
  • Rockville353 Properties
  • Berlin343 Properties
  • Gaithersburg318 Properties
  • Oxon Hill304 Properties
  • Laurel299 Properties
  • Columbia295 Properties
  • Salisbury261 Properties
  • Hanover238 Properties
  • Fort Washington204 Properties
  • Aberdeen202 Properties
  • Takoma Park196 Properties
  • Easton195 Properties
  • Stevensville174 Properties
  • Hyattsville165 Properties
  • Chestertown158 Properties
  • St. Michaels100 Properties
  • College Park92 Properties
  • North Beach57 Properties
  • Mount Rainier53 Properties
  • Accokeek48 Properties
  • Lusby41 Properties
  • West Ocean City21 Properties
  • Emmitsburg11 Properties