Find Vacation Rentals in Chesapeake Beach

We have 87 properties to choose from
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Popular Chesapeake Beach Vacation Rentals

Find the perfect Chesapeake Beach vacation rental

Cottage Chesapeake Beach
from $258 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

121 m² Cottage

5.0
Outstanding(2 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
HomeToGo
Details
Cottage Chesapeake Beach
from $136 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

299 m² Cottage

4.5
Excellent(14 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
HomeToGo
Details
Cottage Chesapeake Beach
from $258 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

89 m² Cottage

4.1
Very good(11 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
HomeToGo
Details
Cottage Chesapeake Beach
from $134 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

300 m² Cottage

4.5
Excellent(14 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Vrbo
Details
House Chesapeake Beach
from $362 per night
House ∙ 6 guests ∙ 3 bedrooms

139 m² House

4.9
Outstanding(64 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Vrbo
Details
House Chesapeake Beach
from $225 per night
House ∙ 6 guests ∙ 3 bedrooms

89 m² House

4.9
Outstanding(86 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Vrbo
Details
House Chesapeake Beach
from $295 per night
House ∙ 8 guests ∙ 3 bedrooms

106 m² House

5.0
Outstanding(13 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Vrbo
Details
House Chesapeake Beach
from $73 per night
4 guests ∙ 2 bedrooms

House

Chesapeake Beach, Sunderland, Maryland, United States
Vrbo
Details
House Chesapeake Beach
from $284 per night
House ∙ 9 guests ∙ 3 bedrooms

158 m² House

5.0
Outstanding(104 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Vrbo
Details
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Vacation Homes With Terraces

House  Chesapeake Beach
from $225 per night
House ∙ 6 guests ∙ 3 bedrooms

89 m² House

4.9
Outstanding(87 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony/Patio
Vrbo
Details
House  Chesapeake Beach
from $284 per night
House ∙ 9 guests ∙ 3 bedrooms

158 m² House

5.0
Outstanding(105 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony/Patio
Vrbo
Details
House  Chesapeake Beach
from $285 per night
9 guests ∙ 4 bedrooms

House

5.0
Outstanding(28 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony/Patio
Vrbo
Details
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Vacation rentals and apartments with air conditioning

Cottage  Chesapeake Beach
from $258 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

121 m² Cottage

5.0
Outstanding(2 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Air conditioning
HomeToGo
Details
House  Chesapeake Beach
from $186 per night
House ∙ 6 guests ∙ 3 bedrooms

166 m² House

4.9
Outstanding(96 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Air conditioning
Vrbo
Details
House  Chesapeake Beach
from $73 per night
4 guests ∙ 2 bedrooms

House

Chesapeake Beach, Sunderland, Maryland, United States
Air conditioning
Vrbo
Details
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Vacation rentals with a balcony

Apartment  Chesapeake Beach
from $467 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

112 m² Apartment

Chesapeake Beach, Sunderland, Maryland, United States
Balcony
Vrbo
Details
House  Chesapeake Beach
from $634 per night
5 guests ∙ 2 bedrooms

House

5.0
Outstanding(10 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony
Vrbo
Details
Condo  Chesapeake Beach
from $268 per night
6 guests ∙ 3 bedrooms

Condo

5.0
Outstanding(3 ratings)
Chesapeake Beach, Sunderland, Maryland, United States
Balcony
Vrbo
Details
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Frequently Asked Questions

How much does it cost to book a vacation rental in Chesapeake Beach?

You can book a vacation rental in Chesapeake Beach for as little as $73 per night.

Are there any vacation rentals available to book in Chesapeake Beach?

There are 87 vacation rental offers in Chesapeake Beach available to book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Chesapeake Beach

Find the best Chesapeake Beach vacation rentals on Tripping.com. With over 49 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Chesapeake Beach range from $106 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 49 homes in Chesapeake Beach offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 6 rentals with pool or jacuzzi, or relax with the family in one of the 47 homes with cable TV. For all those pet owners with dogs or cats, Chesapeake Beach offers 20 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 4 vacation rental sites in Chesapeake Beach where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 41 HomeAway rentals, 4 TripAdvisor short term rentals and 2 Booking.com vacation rentals.

Popular Day Trips Near Chesapeake Beach

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