Minimap with link to location map
Filters
Price
Rating
Distance from Center
Rating (according to Stars)
Facilities

Check availability






Holiday homes in Chesapeake Beach You’ll Love

Top-Rated Chesapeake Beach Holiday homes for Every Budget and Style!

Looking for a holiday home in Chesapeake Beach (Maryland)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chesapeake Beach.

We found 9 Holiday-homes in Chesapeake Beach and the surrounding area (within 50 miles)

Amazing Chesapeake Views Family getaway 4brms in Chesapeake Beach, USA

Amazing Chesapeake Views Family getaway...

Holiday home in Chesapeake Beach, Maryland , 5123 Breezy Point Road
Amazing Chesapeake Views Family getaway 4brms offers accommodations in Chesapeake Beach, a few steps from Breezy Point Beach and 7.1 miles from New Ca...
  • Parking

Very good 4 Reviews 8.5

from $445.45 Show details »

Adorable Beach Cottage with Hot Tub and Tropical Bar! in Chesapeake Beach, USA

Adorable Beach Cottage with Hot Tub and...

Holiday home in Chesapeake Beach, Maryland
Adorable Beach Cottage with Hot Tub and Tropical Bar! offers accommodations in Chesapeake Beach, 30 miles from Addison Road-Seat Pleasant.
  • Parking
  • Bar

Superb 4 Reviews 9.3

from $292.72 Show details »

Coastal Pet-Friendly Cottage Less Than half Mi to Beaches in Chesapeake Beach, USA

Coastal Pet-Friendly Cottage Less Than h...

Holiday home in Chesapeake Beach, Maryland
Coastal Pet-Friendly Cottage Less Than half Mi to Beaches offers accommodations in Chesapeake Beach, a 13-minute walk from North Beach and 28 miles fr...
  • Parking
  • Pets allowed

no reviews

from $99.00 Show details »

Dreamcatchers in North Beach, USA

Dreamcatchers

Holiday home in North Beach near Chesapeake Beach, Maryland , 8320 Bayside Road
Dreamcatchers is located in North Beach, just a 13-minute walk from North Beach and 28 miles from Addison Road-Seat Pleasant.
  • Pets allowed

no reviews

from $56.00 Show details »

North Beach Cottage - Walk to Chesapeake Bay in North Beach, USA

North Beach Cottage - Walk to Chesapeake...

Holiday home in North Beach near Chesapeake Beach, Maryland
North Beach Cottage - Walk to Chesapeake Bay is located in North Beach, just a 5-minute walk from North Beach and 28 miles from Addison Road-Seat Plea...
  • Parking
  • Spa and wellness centre

Exceptional 4 Reviews 10.0

from $281.15 Show details »

Huge Beach Bungalow- Yard, Beach Pass, King Beds in North Beach, USA

Huge Beach Bungalow- Yard, Beach Pass, K...

Holiday home in North Beach near Chesapeake Beach, Maryland , 4005 9th Street
A 7-minute walk from North Beach in North Beach, Huge Beach Bungalow- Yard, Beach Pass, King Beds features accommodations with access to a fitness cen...
  • Parking
  • Pets allowed
  • Fitness centre
  • Family rooms

Exceptional 2 Reviews 10.0

from $179.41 Show details »

Bayfront Maryland Retreat with Deck, Near Beaches! in North Beach, USA

Bayfront Maryland Retreat with Deck, Nea...

Holiday home in North Beach near Chesapeake Beach, Maryland
Bayfront Maryland Retreat with Deck, Near Beaches! offers accommodations in North Beach, 29 miles from Addison Road-Seat Pleasant and 29 miles from An...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Fabulous 1 Reviews 9.0

from $463.17 Show details »

Updated North Beach Cottage Pet Friendly! in Deale, USA

Updated North Beach Cottage Pet Friendly...

Holiday home in Deale near Chesapeake Beach, Maryland
Updated North Beach Cottage Pet Friendly! is located in Deale, just 27 miles from Addison Road-Seat Pleasant and 28 miles from Annapolis Harbor.
  • Parking
  • Pets allowed
  • Spa and wellness centre
  • Outdoor pool
  • Swimming pool

Fabulous 3 Reviews 8.7

from $261.39 Show details »

Waterfront North Beach Home about 2 Mi to Beach! in Deale, USA

Waterfront North Beach Home about 2 Mi t...

Holiday home in Deale near Chesapeake Beach, Maryland
Waterfront North Beach Home about 2 Mi to Beach! offers accommodations in Deale, 28 miles from Annapolis Harbor.
  • Parking
  • Pets allowed
  • Spa and wellness centre

Exceptional 1 Reviews 10.0

from $379.78 Show details »

Number of Holiday homes in Chesapeake Beach 9
Number of guest ratings 398
Average price per night $314.00
Lowest price per night $50,00
Highest price per night $9.044,24

Top 10 Cheapest Holiday-homes in Chesapeake Beach

Discover the Cheapest Holiday-homes in Chesapeake Beach – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chesapeake Beach

Check out the Most Booked Holiday-homes in Chesapeake Beach – Based on Guest Popularity.

Holiday homes in Chesapeake Beach (Maryland), comfortable and familiar

Staying in a holiday or vacation home in Chesapeake Beach can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chesapeake Beach for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chesapeake Beach should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com