Chesapeake Beach holiday rentals: compare the best deals
Chesapeake Beach
06/27 – 07/04
HK$1776/nighttotal: HK$12432 (7 )
Bay Front Beach Access Guest Loft
1 2
house , Deale
This private loft apartment in Deale is situated in a quiet waterfront neighbourhood, offering convenient access to Annapolis, and is within a 50-kilometre drive of the DC and Baltimore metropolitan areas. This accommodation, suitable for two guests, features a bedroom, bathroom, kitchen, and living room, with air conditioning, internet, and a shared laundry room available.
9.8 130 reviews
Chesapeake Beach
06/27 – 07/04
HK$2465/nighttotal: HK$17255 (7 )
Patuxent River View
2 2
house , Dunkirk
This Dunkirk guest house is situated near North Beach, Maryland, approximately 65km from Washington D.C., offering easy access to Annapolis, Baltimore, and Solomons Island. This 84 square metre self-catering property features two bedrooms, one bathroom, a fully equipped kitchen, and a swimming pool, sleeping up to four guests and providing a comfortable stay with free Wi-Fi and spectacular views.
10 26 reviews
Chesapeake Beach
07/17 – 07/20
HK$3736/nighttotal: HK$11208 (3 )
Family Bay Escape | Firepit • Bbq • Beach Passes
3 2
apartment , North Beach
This three-bedroom, two-bathroom holiday home is situated on the quieter side of North Beach, a short walk from restaurants, the boardwalk, beaches, and the wetland overlook nature park, and a 5-minute (approx. 8 km) drive from Rod & Reel Resort and Herrington Harbour South. The property boasts a serene private backyard with a fire pit, a sun porch, and includes amenities such as a fully equipped kitchen with dishwasher, air conditioning, internet access, parking, and comfortably sleeps six guests.
Chesapeake Beach
07/17 – 07/20
HK$6013/nighttotal: HK$18039 (3 )
3-bedroom Beach Home W/ Backyard
3 2
apartment , North Beach
This North Beach flat is located a 1-minute walk from the Bay water beach and within a 5-kilometre drive of the North Beach Boardwalk and popular waterfront dining. This 130-square-metre, 3-bedroom flat accommodates up to 5 guests, offering a private garden with outdoor dining, a sunroom, a fully equipped kitchen, and parking for up to 6 vehicles, including a Tesla charger.
9.2 5 reviews
Chesapeake Beach
07/12 – 07/18
HK$3335/nighttotal: HK$20010 (6 )
Waterfront Lux Cottage With Amazing Views Near Dc
2 2
apartment , North Beach
This North Beach waterfront holiday home is situated near Chesapeake Beach, Maryland, offering easy access to the Bayside History Museum and Chesapeake Beach Railway Museum, and is approximately 60km from Washington, D.C. The two-bedroom, two-bathroom property sleeps six guests and boasts direct Chesapeake Bay access, ideal for boating and fishing, with a kitchen and all necessary sleeping accommodations.
8.0 13 reviews
Chesapeake Beach
06/27 – 07/04
HK$2459/nighttotal: HK$17213 (7 )
Chesapeake Bay Loft Retreat, Walk To Water, Sleeps 2, 20 Min To Annapolis
1 2
apartment , Deale
This waterfront flat is situated in Deale, Maryland, just 9.6km from Franklin Point State Park, Shadyside Park, and Captain Avery Museum, and 14.5km from Galesville Heritage Museum and Sand Point Marsh. The property is highly rated by guests, receiving a "very good" user rating. The apartment offers a comfortable 56 square metre space, ideal for up to 4 guests. You'll find a fully equipped kitchen, a private balcony, free Wi-Fi, and a garden, perfect for enjoying the beautiful surroundings.
10 8 reviews
Chesapeake Beach
07/12 – 07/18
HK$4165/nighttotal: HK$24990 (6 )
Summer Breeze Family Retreat | North Beach
1 2
apartment , North Beach
This spacious 2,700+ sq ft apartment in North Beach is situated just four blocks from the waterfront and boardwalk, placing you within a 10-minute walk of the beach, shops, restaurants, and breweries, with a private two-car driveway offering rare convenience in this walkable community. This four-bedroom, four-and-a-half-bathroom residence accommodates up to eight guests, featuring two primary suites, an upper-level bonus room, a rear deck for outdoor enjoyment, and a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher, all supported by air conditioning and internet.
10 2 reviews
Chesapeake Beach
06/27 – 07/04
HK$1208/nighttotal: HK$8456 (7 )
Welcome To The Peace Of Nature
1 2
apartment , Chesapeake Beach
This Chesapeake Beach apartment offers a central location, providing convenient access to local attractions, though precise distances to landmarks such as the Chesapeake Beach boardwalk remain unspecified. The one-bedroom, one-bathroom flat sleeps four guests and includes air conditioning and internet access; further details on the property's size or specific amenities are unavailable.
Chesapeake Beach
06/27 – 07/04
HK$2371/nighttotal: HK$16597 (7 )
Chesapeake Bay Views • Sleeps 8 • Walk To Beach
3 2
apartment , Chesapeake Beach
This Chesapeake Beach holiday let offers direct views of the Chesapeake Bay, situated just 200 metres from a private community beach, with Breezy Point Beach a few minutes away and North Beach a 10-kilometre drive. This family-friendly apartment sleeps eight across three bedrooms, featuring two king-size rooms and a third with two double beds, boasting a fully equipped kitchen, Wi-Fi, air conditioning, a garden, parking for three vehicles, and opportunities for beachcombing and fossil hunting.
10 1 review
Chesapeake Beach
06/27 – 07/04
HK$6696/nighttotal: HK$46872 (7 )
Sweet Deale Villa
1 5
apartment , Deale
This Deale, Maryland waterfront property boasts over 30 metres of private access to the Chesapeake Bay, offering stunning views of a nearby bridge and proximity to Deale's town centre (distance unspecified). The four-bedroom, three-bathroom house sleeps twelve guests and features a large concrete patio, rooftop deck, and completely remodelled interior, including air conditioning, parking, and internet access.
9.6 4 reviews
Chesapeake Beach
07/12 – 07/18
HK$1661/nighttotal: HK$9966 (6 )
Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md.
2 2
cottage , North Beach
This holiday let in North Beach is located 800 metres from the Chesapeake Bay and 800 metres from the Bayside History Museum. This holiday let offers Wi-Fi, air conditioning, a dishwasher, and a microwave oven, with parking and laundry facilities available on site.
8.6 1686 reviews
Chesapeake Beach
07/12 – 07/18
HK$2157/nighttotal: HK$12942 (6 )
Rod 'N' Reel Resort
1 2
resort , Chesapeake Beach
Rod 'N' Reel Resort is situated on the Chesapeake Bay, a short drive from North Beach and Twin Shields Golf Club, making it a convenient base for exploring the area. The resort enjoys excellent ratings for its location, cleanliness, and overall experience. The resort offers a range of accommodation options, including rooms with balconies and water views. Guests can enjoy a variety of amenities, including a swimming pool, fitness centre, spa, and on-site dining options, as well as activities like fishing charters and casino entertainment.
Best family friendly Chesapeake Beach holiday rentals
Among the 3 accommodations in Chesapeake Beach, here are the 3 best family friendly rentals
10 90 reviews
Chesapeake Beach
07/17 – 07/20
HK$3832/nighttotal: HK$11496 (3 )
Charming 4bdrm 3bath House 2king Beds 1queen& Bunk
1 2
apartment , Chesapeake Beach
This 4-bedroom house is conveniently located in Chesapeake Beach, Maryland, just 4 kilometres from Herrington on the Bay and North Beach, and 3 kilometres from the Chesapeake Beach boat docks and Rod 'N' Reel Resort. The property has received excellent ratings for location, cleanliness and overall user experience. This split-level home is ideal for families or groups of friends, with a capacity of 9 guests and features three full bathrooms. The house is equipped with modern amenities such as Wi-Fi, cable TV, a smart TV and a Blu-ray player, as well as a fully equipped kitchen with a dishwasher and a large deck for outdoor dining.
10 11 reviews
Chesapeake Beach
07/17 – 07/20
HK$5170/nighttotal: HK$15510 (3 )
Bayfront Home W/hot Tub
2 2
apartment , North Beach
This North Beach holiday home is situated within 3.2km of the Bayside History Museum, Chesapeake Beach Water Park, and Rod n Reel Charter Fishing, and 2.6km from the Chesapeake Beach Railway Museum. This two-bedroom, three-bathroom property sleeps five guests and boasts a fully equipped kitchen, Jacuzzi, fitness centre, terrace, garden, parking, and in-unit laundry facilities, alongside nearby barbecue grills.
10 11 reviews
Chesapeake Beach
06/27 – 07/04
HK$3620/nighttotal: HK$25340 (7 )
2 Blocks From Bay! Community Beach! Boat Launch! Kayak! Hike! Fossil Hunt!
4 2
apartment , Prince Frederick
This Prince Frederick holiday home is situated within 9.6km of CSA Park, Calvert Historical Society Park, and Fox Run Centre, offering easy access to local attractions. This spacious 162 square metre property boasts four bedrooms, two bathrooms, sleeping up to ten guests, and features a private garden, swimming pool, spa, and barbecue facilities, alongside free Wi-Fi.
Best Chesapeake Beach holiday rentals with parking
Chesapeake Beach
06/27 – 07/04
HK$2846/nighttotal: HK$19922 (7 )
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
1 5
apartment , North Beach
This three-bedroom property is located in the quiet waterfront Rose Haven district of North Beach, Maryland, offering views of the Chesapeake Bay and being a short 10-minute drive from Chesapeake Beach and 32 kilometres from Annapolis. This apartment boasts a garden with a grill and firepit, air conditioning, a fully equipped kitchen including a dishwasher, and parking, comfortably accommodating up to six guests.
9.7 235 reviews
Chesapeake Beach
07/12 – 07/18
HK$1784/nighttotal: HK$10704 (6 )
Guest Quarters At The Inn - 205
1 2
apartment , North Beach
This one-bedroom flat is situated in Chesapeake Beach, just a short distance from the Bayside History Museum, Chesapeake Beach Water Park, and Rod n Reel Charter Fishing, offering easy access to the area's attractions. The property enjoys excellent user, location, and cleanliness ratings. The flat provides a comfortable living space with a fully equipped kitchen and a balcony for outdoor relaxation. Amenities include a swimming pool, a garden, and parking, as well as free Wi-Fi, air conditioning, and the option to bring pets.
10 7 reviews
Chesapeake Beach
07/12 – 07/18
HK$3200/nighttotal: HK$19200 (6 )
The Mermaid Cottage
1 2
apartment , North Beach
This two-bedroom flat, "Mermaid Cottage," is situated in a residential area of North Beach, just 3 blocks from the Chesapeake Bay waterfront and boardwalk. This apartment accommodates up to four guests and features a well-equipped kitchen with a Nespresso machine, air conditioning, parking, and a fenced garden with an outdoor dining area and gas grill, all within easy walking distance of boardwalk attractions.
10 1 review
Chesapeake Beach
07/12 – 07/18
HK$6899/nighttotal: HK$41394 (6 )
Your Perfect Waterfront Oasis Overlooking The Chesapeake Bay Awaits!
3 2
apartment , North Beach
This North Beach holiday apartment, a short distance from the Bayside History Museum and Chesapeake Beach Railway Museum, offers convenient access to local attractions. The 184 square metre (1975 square feet) property boasts three bedrooms, three bathrooms, sleeps seven guests, and includes a fully equipped kitchen, air conditioning, in-unit laundry, and smart TVs.
Frequently asked questions about holiday rentals in Chesapeake Beach
What are some interesting places to visit in or near Chesapeake Beach, MD?
Chesapeake Beach is a lovely town with a lot to offer. You must visit the Chesapeake Beach Railway Museum to learn about the area's rich history. For a day of fun in the sun, head to the Chesapeake Beach Waterpark. And if you're looking for a scenic drive, take a trip to the Calvert Cliffs State Park, which is a short drive away.
What are the best Airbnb and vacation rentals in Chesapeake Beach?
Which walking or cycling routes are the best in Chesapeake Beach, MD?
The Chesapeake Beach boardwalk is a great place for a leisurely stroll or bike ride. It stretches along the waterfront and offers beautiful views of the Chesapeake Bay. For a longer ride, try the Calvert Cliffs State Park trail, which winds through the woods and offers stunning views of the cliffs.
What are the most popular Airbnbs in Chesapeake Beach?
What sports or outdoor activites can visitors enjoy in and around Chesapeake Beach, MD?
Chesapeake Beach is a haven for outdoor enthusiasts. You can go fishing, kayaking, or paddleboarding in the Chesapeake Bay. If you're feeling adventurous, try parasailing or jet skiing. There are also plenty of opportunities for hiking and biking in the surrounding area.
What are the best vacation rentals with a pool in Chesapeake Beach?
What other towns or cities can be easily accessed from Chesapeake Beach, MD?
From Chesapeake Beach, you can easily visit Annapolis, the capital of Maryland, which is about a 45-minute drive away. You can also explore the charming towns of Solomons and St. Michaels, both known for their beautiful waterfront settings and seafood restaurants.
What are the best rentals for families and kids in Chesapeake Beach?
What amenities are commonly available in vacation rentals in Chesapeake Beach, MD?
Most vacation rentals in Chesapeake Beach come equipped with basic amenities like a kitchen, bathroom, and bedrooms. Many also offer extras like Wi-Fi, laundry facilities, and private decks or patios. Some even have access to pools or hot tubs.
What are the best rentals or Airbnbs with a jacuzzi in Chesapeake Beach?
What time of year is best to rent a vacation rental Chesapeake Beach, MD?
The best time to visit Chesapeake Beach is during the summer months, from June to August, when the weather is warm and sunny. You can enjoy swimming, boating, and all the other outdoor activities the area has to offer. However, if you prefer a quieter experience, spring or autumn are also good choices.
What are the local dishes in Chesapeake Beach, MD region?
Chesapeake Beach is known for its fresh seafood. Some local favourites include crab cakes, steamed crabs, and oyster stew. You can find these dishes at many restaurants in town, especially those located along the waterfront.
Destinations nearby
Best Chesapeake Beach holiday rentals with a balcony
10 2 reviews
Chesapeake Beach
07/12 – 07/18
HK$11997/nighttotal: HK$71982 (6 )
Waterfront- 5-bedroom House With Dock In Charming North Beach
5 2
apartment , North Beach
This spacious North Beach property, a five-bedroom house with six bathrooms, boasts a stunning waterfront location with a private dock, offering breathtaking Chesapeake Bay sunsets and proximity to the Bayside History Museum and Chesapeake Beach Railway Museum. The 483-square-metre (5200 sq ft) residence features three levels, an elevator, a gourmet kitchen, three-level deck with firepit, a Tesla charging station, and sleeps up to 18 guests, providing ample space for family gatherings and enjoying nearby fishing, birdwatching, and exploring the Fridays Creek Winery.
10 2 reviews
Chesapeake Beach
07/12 – 07/18
HK$3591/nighttotal: HK$21546 (6 )
Rising Sun Bay View Cottage W/ Beach Views!
3 2
apartment , Chesapeake Beach
This Chesapeake Beach waterfront holiday home boasts direct beach access and stunning Chesapeake Bay views, situated near the Rod n' Reel Charter Fishing and R&J's PlayPark. The 295 square metre (approximately 3174 square feet) property offers a spacious layout sleeping six guests across four bedrooms and five bathrooms, including a fully equipped kitchen, free Wi-Fi, and a screened porch.
Best pet friendly Chesapeake Beach holiday rentals
Among the 4 accommodations in Chesapeake Beach, here are the 4 best pet friendly rentals
9.6 10 reviews
Chesapeake Beach
07/17 – 07/20
HK$3294/nighttotal: HK$9882 (3 )
4br North Beach Home W/ Decks, Firepit & Game Room
1 2
apartment , North Beach
This North Beach flat is located in a sought-after district, offering excellent access to local attractions and the seaside. This spacious 179 square metre flat accommodates up to eight guests and features four bedrooms, two bathrooms, a dedicated office with a standing desk, in-unit laundry, a remodelled lower-level suite with private walkout, two large decks, a fenced yard with a fire pit, and ample parking.
10 177 reviews
Chesapeake Beach
07/17 – 07/20
HK$5253/nighttotal: HK$15759 (3 )
Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces
1 2
apartment , North Beach
This waterfront flat is located in North Beach, just a short walk from the beach, pier, and several bars and restaurants. It has received excellent ratings for location, cleanliness, and user experience. This two-bedroom, two-bathroom property can accommodate up to five guests. Enjoy amenities like a fully equipped kitchen, a private hot tub, a Peloton bike and treadmill, two cruising bikes, and a back deck with a Solo stove.
8.0 1 review
Chesapeake Beach
07/12 – 07/18
HK$5714/nighttotal: HK$34284 (6 )
3 Bedroom, Waterfront Cottage On The Shores Of The Chesapeake Bay.
3 2
cottage , North Beach
This North Beach holiday home enjoys a beachfront location directly on the boardwalk, offering unparalleled access to the Chesapeake Bay and is within walking distance of local restaurants, shops, and the farmers' market. The three-bedroom, two-bathroom property sleeps eight guests and features an open-plan layout with high ceilings, a rear patio with fire pit, and internet access; nearby attractions include the Bayside History Museum and Chesapeake Beach Railway Museum.
9.9 77 reviews
Chesapeake Beach
07/12 – 07/18
HK$5936/nighttotal: HK$35616 (6 )
Beachfront Paradise | Walk To Restaurants & Shops
1 2
apartment , North Beach
This apartment is directly on the North Beach boardwalk, just a short walk from restaurants, shops, and the weekly farmer's market, offering a convenient and lively location. It has received excellent ratings for location, cleanliness, and overall experience. The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious kitchen, outdoor patio with fire pit, and direct beach access, perfect for a relaxing and enjoyable stay.