Vacation Homes in Chesapeake Beach, MD

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Vacation Homes in Chesapeake Beach

Don't see what you're looking for?
See all available properties in Chesapeake Beach
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Chesapeake Beach

Find the Best Vacation Homes in Chesapeake Beach

Why book a vacation home in Chesapeake Beach?

Vacation homes in Chesapeake Beach make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.

How much is a vacation home in Chesapeake Beach?

Private Chesapeake Beach rental homes range between $90 - $263 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.

What are the cancellation and flexibility options on Travelocity?

To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.

What amenities should I look out for in a vacation home?

There are some exciting amenities available in Chesapeake Beach vacation home rentals. You might look for Chesapeake Beach rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room. 

Vacation rentals in Chesapeake Beach offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.

When is the best time to rent a vacation home in Chesapeake Beach?

You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.

Why book a vacation home with Travelocity?

Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Chesapeake Beach. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Chesapeake Beach hotels and vacation homes that best suit your stay. We also have deals for flights, and Chesapeake Beach car rentals. You’ll save even more when you bundle your items into a Chesapeake Beach vacation package!

How many vacation homes are available to book in Chesapeake Beach?

There are 402 rental homes in Chesapeake Beach. Enter your travel dates to check availability.

How do I find the best price for a vacation home in Chesapeake Beach?

Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.

Chesapeake Beach Vacation Homes essential information

Accommodation
402 Vacation Homes
Lowest Price
$90
Highest Price
$263
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Million Dollar View of the Chesapeake Bay, Walk to Everything House, Relax on Kent Island in 3 Bedroom Home w/Waterview, Private Waterfront Woods | Dock, Kayaks, Views, Waterfront- 5-bedroom house with dock in charming North Beach, Sweet Bamboo Beach Cottage, NEW: Life on the River! Luxury estate with jacuzzi and private pier!, Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis, Newly Updated EV Charger Ready Peaceful Home in Annapolis

Explore More Ways to Travel with Travelocity