113+ Vacation Rentals & Holiday Homes in Chesapeake Beach |
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Chesapeake Beach Accommodations - Hotels & Rentals

About Chesapeake Beach Vacation Rentals

Discover More than 113 Incredible Getaway Rentals Available in Chesapeake Beach. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Chesapeake Beach.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Chesapeake Beach, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Chesapeake Beach. The Average Size of Places to Stay Near Chesapeake Beach is 1033.61 ft², with Prices Averaging US $342 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Chesapeake Beach. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Chesapeake Beach

Type Count
Vacation Homes 82
Holiday Apartments 14
Cottages 14

Use these Quick Filters to Find a Vacation Rental in Chesapeake Beach

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Chesapeake Beach with Online Reservations.

Weather in Chesapeake Beach, MD

View the weather forecast for Chesapeake Beach before booking your Chesapeake Beach Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Chesapeake BeachGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Chesapeake BeachGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Chesapeake Beach Water Park
Rod n Reel Charter Fishing
Breezy Point Beach
Bruce Gabrielson's Surf Art Gallery and Museum
Chesapeake Beach Railway Museum
Six Flags America
Show Place Arena
Calvert Cliffs State Park
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
St. Michaels Winery
Allen Pond Park
Chesapeake Bay Maritime Museum
Oxford Museum
Maryland Quiet Waters Park
St John's College
St. Charles Towne Center
Renditions Golf Club
Cove Point Lighthouse
Running Hare Vineyard

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Bruce Gabrielson's Surf Art Gallery and Museum 95 Properties
Chesapeake Beach Water Park 82 Properties
Chesapeake Beach Railway Museum 82 Properties
Rod n Reel Charter Fishing 82 Properties
Breezy Point Beach 49 Properties

Frequently Asked Questions About Chesapeake Beach?

What are the top hotels, lake houses & vacation rentals in Chesapeake Beach?

We provide an array of great vacation destinations in Chesapeake Beach. If you are looking to stay in or around the Chesapeake Beach area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Chesapeake Beach:

Which hotel, lake house, or vacation rental in Chesapeake Beach is best for families?

Searching for a family-friendly getaway in Chesapeake Beach? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Chesapeake Beach?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 113 in the Chesapeake Beach area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Chesapeake Beach.


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Online Reservation in Chesapeake Beach

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