Holiday Rentals in Chesapeake Beach

12 available vacation rental offers

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Chesapeake Beach holiday rentals
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Chesapeake Beach holiday rentals: compare the best deals

Best family friendly Chesapeake Beach holiday rentals

Among the 4 accommodations in Chesapeake Beach, here are the 4 best family friendly rentals

Bayview, Walk To Beach & Boardwalk Perfect Getaway - Chesapeake Beach
10 6 reviews
Chesapeake Beach
07/20 – 07/24
HK$8407/nighttotal: HK$33628 (4 )

Bayview, Walk To Beach & Boardwalk Perfect Getaway

1 6
apartment , North Beach
This spacious three-storey apartment in North Beach is a short walk from the North Beach Boardwalk, offering easy access to shops and restaurants.
Sleeping up to 13 guests, the property boasts four bedrooms (two with bunk beds), two bathrooms, a game room, three decks with bay views, and amenities including a fridge, microwave, dishwasher, air conditioning, internet access, a garden, and parking.
Patuxent River View - Chesapeake Beach
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.
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Chesapeake Beach
10 52 reviews
Chesapeake Beach
06/27 – 07/04
HK$2474/nighttotal: HK$17318 (7 )

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

2 2
cottage , Dunkirk
This charming cottage is situated just a short distance from Fridays Creek Winery and the Patuxent River, offering a peaceful escape in the heart of Dunkirk, Maryland. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage spans 84 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private outdoor pool, barbecue grills, and a spacious garden, as well as the convenience of a fully equipped kitchen, free Wi-Fi and a private patio.
Charming 4bdrm 3bath House 2king Beds 1queen& Bunk - Chesapeake Beach
10 90 reviews
Chesapeake Beach
07/20 – 07/24
HK$3679/nighttotal: HK$14716 (4 )

Charming 4bdrm 3bath House 2king Beds 1queen& Bunk

4 6
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.

Best Chesapeake Beach holiday rentals with parking

Sweet Bamboo Beach Cottage - Chesapeake Beach
9.8 129 reviews
Chesapeake Beach
07/20 – 07/24
HK$2012/nighttotal: HK$8048 (4 )

Sweet Bamboo Beach Cottage

3 6
apartment , North Beach
This North Beach apartment is a short walk from the beach, boardwalk, and restaurants, and just five minutes from Chesapeake Beach. It has received excellent ratings for location, cleanliness, and user experience.
The three-bedroom property is spacious, with 89 square metres of floor area, and can comfortably accommodate up to six guests. The apartment is fully renovated and offers a range of amenities, including a well-equipped kitchen, air conditioning, a garden, a spa, parking, and internet access.
Bayfront Maryland Retreat W/ Deck, Near Beaches! - Chesapeake Beach
9.4 15 reviews
Chesapeake Beach
07/20 – 07/24
HK$3944/nighttotal: HK$15776 (4 )

Bayfront Maryland Retreat W/ Deck, Near Beaches!

3 6
apartment , North Beach
This waterfront property in North Beach, Maryland is situated within 4.8 kilometres of the Bayside History Museum, Chesapeake Beach Water Park, and Rod n Reel Charter Fishing, and 4 kilometres from the Chesapeake Beach Railway Museum.
This four-bedroom, two-bathroom holiday home boasts 121 square metres of living space, sleeping up to eight guests and offering a fully equipped kitchen, private patio, spa, parking and free Wi-Fi.
Walk To Beach! King Bed & Free Beach Passes - Chesapeake Beach
10 21 reviews
Chesapeake Beach
07/20 – 07/24
HK$3241/nighttotal: HK$12964 (4 )

Walk To Beach! King Bed & Free Beach Passes

3 6
apartment , North Beach
This three-bedroom apartment is located in North Beach, a short 1.9km walk from the beach, boardwalk, restaurants, and children's play areas. It's also a 5.6km drive from Herrington Harbor, offering a peaceful escape in a quiet neighbourhood. The apartment has received excellent user ratings and is perfect for families or groups of up to six guests.
The apartment offers a spacious 104 square metres of living space and is equipped with everything you need for a comfortable stay. It boasts a fully equipped kitchen, a garden with a deck, a dedicated workspace, and family-friendly amenities like a pack-n-play, a booster seat, and beach chairs.
Guest Quarters At The Inn - 205 - Chesapeake Beach
9.7 237 reviews
Chesapeake Beach
06/27 – 07/04
HK$1974/nighttotal: HK$13818 (7 )

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.

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?

    Guest Quarters At The Inn - 205, Club Carp North Beach and Beach Home | King Bed | Beach Passes | Cute Town are the most popular Airbnb and vacation rentals in Chesapeake Beach among travelers.

  • 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?

    Among the Airbnbs in Chesapeake Beach, Guest Quarters At The Inn - 205, Club Carp North Beach and Beach Home | King Bed | Beach Passes | Cute Town are the most popular ones.

  • 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

Rod 'N' Reel Resort - Chesapeake Beach
8.6 1686 reviews
Chesapeake Beach
06/28 – 07/09
HK$1727/nighttotal: HK$18997 (11 )

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.
Chesapeake Bay Loft Retreat, Walk To Water, Sleeps 2,  20 Min To Annapolis - Chesapeake Beach
8.0 13 reviews
Chesapeake Beach
06/28 – 07/09
HK$2368/nighttotal: HK$26048 (11 )

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.
Updated North Beach Cottage Pet Friendly! - Chesapeake Beach
9.6 74 reviews
Chesapeake Beach
07/20 – 07/24
HK$2441/nighttotal: HK$9764 (4 )

Updated North Beach Cottage Pet Friendly!

3 6
house , North Beach
This North Beach cottage is located in Deale, Maryland, just 43 kilometres from Annapolis Harbour and 43 kilometres from Addison Road-Seat Pleasant. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The cottage offers 3 bedrooms and 2 bathrooms across 134 square metres, comfortably accommodating up to 8 guests. The property is pet-friendly, air-conditioned, and includes a swimming pool, spa, garden, parking, a fully equipped kitchen, washing machine, Wi-Fi, cable TV, and a patio.

Best pet friendly Chesapeake Beach holiday rentals

Among the 4 accommodations in Chesapeake Beach, here are the 4 best pet friendly rentals

Bayfront Maryland Retreat W/ Deck, Near Beaches! - Chesapeake Beach
9.7 18 reviews
Chesapeake Beach
07/20 – 07/24
HK$3060/nighttotal: HK$12240 (4 )

Bayfront Maryland Retreat W/ Deck, Near Beaches!

3 6
apartment , North Beach
This North Beach holiday home is situated in a peaceful neighbourhood, just a short stroll from the lively boardwalk and the sandy shores of the Chesapeake Bay.
The property offers three bedrooms, two bathrooms, and a sleeper sofa, comfortably accommodating up to eight guests. Guests can enjoy a fully equipped kitchen, a spacious deck with outdoor seating, free Wi-Fi, and parking.
Spacious Beach House Top Floors - Walk Everywhere! - Chesapeake Beach
9.8 103 reviews
Chesapeake Beach
07/20 – 07/24
HK$1560/nighttotal: HK$6240 (4 )

Spacious Beach House Top Floors - Walk Everywhere!

3 6
apartment , North Beach
This North Beach duplex apartment, located 0.32 kilometres from the beach and promenade, offers easy access to North Beach's attractions.
The two-bedroom, one-bathroom property sleeps eight guests, features a fully equipped kitchen with dishwasher, in-unit laundry, and a shared deck with barbecue; a king, full, and twin bed are available in the loft area.
Bayviews - Chesapeake Beach
9.7 58 reviews
Chesapeake Beach
07/20 – 07/24
HK$8609/nighttotal: HK$34436 (4 )

Bayviews

4 6
apartment , North Beach
This four-bedroom apartment is situated in North Beach, just a short walk from the waterfront and the bustling city centre. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travellers.
The spacious home has two bathrooms and can accommodate up to eight guests. This North Beach apartment comes with a range of amenities, including a garden, parking, air conditioning, and internet access, as well as a kitchen equipped with a fridge. Guests can also enjoy the three decks, offering stunning bay views and perfect for relaxing or entertaining.
4br North Beach Home W/ Decks, Firepit & Game Room - Chesapeake Beach
9.6 11 reviews
Chesapeake Beach
07/20 – 07/24
HK$2541/nighttotal: HK$10164 (4 )

4br North Beach Home W/ Decks, Firepit & Game Room

1 6
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.
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