Discover a selection of 403 holiday rentals in Chesapeake Beach that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 109 per night, and houses and cabins are popular options for a stay in Chesapeake Beach. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chesapeake Beach
Destination guide

Head to the relaxing city of Chesapeake Beach

Enjoy the live music and other features of Chesapeake Beach. Travellers especially like the restaurants, spas and beaches in this relaxing and romantic city. Whether you're planning a family holiday, a trip with friends or a romantic retreat, Vrbo has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.


Sightseeing in and around Chesapeake Beach

Are you hoping to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Chesapeake Beach a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chesapeake Beach Water Park (0.1 mi / 0.2 km)
  • Running Hare Vineyard (13.6 mi / 21.9 km)
  • Lake Presidential Golf Club (14.9 mi / 24 km)
  • Perigeaux Vineyards and Winery (19 mi / 30.6 km)

Seasonal weather in Chesapeake Beach

If you're planning a holiday around the weather, July, June, August and September are the hottest months to visit, when temperatures average 31°F.

Natural features

Exploring the natural landscape of Chesapeake Beach

Whether you're an active traveller or just want to appreciate the scenery, Chesapeake Beach is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Breezy Point Beach (5.3 mi / 8.5 km)
  • Shadyside Park (10.6 mi / 17 km)
  • Jefferson Patterson Park and Museum (20.4 mi / 32.9 km)
  • Kent Island (20.9 mi / 33.6 km)
How to get there

How to get to and around Chesapeake Beach

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 26.5 mi (42.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into College Park, MD (CGS), which is 28.8 mi (46.3 km) away.

Can I find a vacation rental around Chesapeake Beach?

Yes, our 2021 property listings offer a large selection of 403 vacation rentals near Chesapeake Beach. From 321 houses to 26 cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chesapeake Beach for a holiday or a weekend are on Vrbo.