Book Holiday Homes in Chesapeake Beach

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Featured Holiday Homes in Chesapeake Beach

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.3 mi (10.2 km) from Ragged Island and 7.7 mi (12.4 km) from Spocott ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Walk to Everything House
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Brand New Spacious Luxury Home

Brand New Spacious Luxury Home

Annapolis
With a stay at this vacation home in Annapolis, you'll be within a 5-minute drive of U.S. Naval Academy and Spa Creek.
Brand New Spacious Luxury Home
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard
With a stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Jefferson Patterson Park and Museum and a 3-minute drive from Perigeaux ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Waterfront Cheerful 6 BR Home with Private Pier

Waterfront Cheerful 6 BR Home with Private Pier

Edgewater
Located in Edgewater, this vacation home is on the waterfront, within a 10-minute drive of South River Golf Links and London Town.
Waterfront Cheerful 6 BR Home with Private Pier
Serene waterfront sunsets in this sprawling historic Annapolis home

Serene waterfront sunsets in this sprawling historic Annapolis home

Annapolis
With a stay at this vacation home in Annapolis (Hillsmere), you'll be within a 15-minute drive of U.S. Naval Academy and Maryland Quiet Waters Park.
Serene waterfront sunsets in this sprawling historic Annapolis home
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Annapolis
Located in Annapolis, this vacation home is on the waterfront, a 3-minute drive from Bay Ridge Beach and 6 minutes from Bay Bridge Market Place Shopping ...
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
Pet-Friendly Annapolis Home: Walk to Beach!

Pet-Friendly Annapolis Home: Walk to Beach!

Annapolis
With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Pet-Friendly Annapolis Home: Walk to Beach!
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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.

Chesapeake Beach Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesapeake Beach vacation homes are the perfect way for you to wing it.

Holiday houses in Chesapeake Beach let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesapeake Beach in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesapeake Beach adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesapeake Beach with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesapeake Beach vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesapeake Beach Holiday Homes essential information

Accommodation
320 Holiday Homes
Lowest Price
AU$113
Highest Price
AU$227
Popular accommodation
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Walk to Everything House, Brand New Spacious Luxury Home, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Waterfront Cheerful 6 BR Home with Private Pier, Serene waterfront sunsets in this sprawling historic Annapolis home, Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D, Pet-Friendly Annapolis Home: Walk to Beach!

Top trending hotels in Chesapeake Beach

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$227 per night from 2 Mar to 3 Mar
AU$227
includes taxes & fees
2 Mar - 3 Mar
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and 3 minutes by foot ...
Rod 'N' Reel Resort
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Chesapeake Beach
Located in Chesapeake Beach, this vacation home is on the waterfront, a 4-minute drive from Bruce Gabrielson's Surf Art Gallery and Museum and 5 minutes from ...
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views

Chesapeake Beach
With a stay at this vacation home in Chesapeake Beach, you'll be on the beach, just steps from Breezy Point Beach and a 4-minute drive from Bruce Gabrielson's ...
Family Beach House: Spacious Deck, Grill & Views
Save an average of 15% on thousands of hotels when you're signed in
Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

2 out of 5
7851 Malcolm Road, Clinton, MD
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 23 Feb to 24 Feb
AU$113
includes taxes & fees
23 Feb - 24 Feb
With a stay at Econo Lodge Andrews Air Force Base, you'll be centrally located in Clinton, within a 15-minute drive of MGM National Harbor Casino and The Theater ...
Econo Lodge Andrews Air Force Base
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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.

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^Subject to availability and chosen travel dates.