The 10 best holiday homes in Chesapeake Beach, USA | Booking.com
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Holiday Homes in Chesapeake Beach

Find the holiday homes that appeal to you the most

The best holiday homes in Chesapeake Beach

Check out our pick of great holiday homes in Chesapeake Beach

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Edgewatermayo Getaway!

Edgewater (Near Chesapeake Beach)

Featuring a spa bath, Edgewatermayo Getaway! is set in Edgewater. The air-conditioned accommodation is 19 km from Annapolis Harbor, and guests can benefit from on-site private parking and...

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews
Price from
US$261
1 night, 2 adults
Check availability

Calloway Drive Retreat

Deale (Near Chesapeake Beach)

Set in Deale, 35 km from Annapolis Harbor and 46 km from Addison Road-Seat Pleasant, Calloway Drive Retreat offers a restaurant. Guests can benefit from a patio and a children's playground.

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
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Searenity Stays

Edgewater (Near Chesapeake Beach)

Set in Edgewater in the Maryland region and Triton Beach reachable within 700 metres, Searenity Stays offers accommodation with free WiFi, a children's playground, a private beach area and free...

M
Margot
From
Ireland
Everything is spotlessly clean and it is a very very comfortable house. The location is lovely, in a very quiet residential neighbourhood. It is the nicest holiday rental we have ever stayed in.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 12 reviews
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All holiday homes in Chesapeake Beach

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Chesapeake Beach and surroundings in the past month

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Enjoy breakfast in Chesapeake Beach and nearby

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 4 reviews

    Situated in North Beach, 400 metres from North Beach and 46 km from Addison Road-Seat Pleasant, North Beach Cottage - Walk to Chesapeake Bay offers a garden and air conditioning.

  • Situated in North Beach, 800 metres from North Beach and 46 km from Addison Road-Seat Pleasant, The North Beach Retreat House offers air conditioning.

  • Set in North Beach, 200 metres from North Beach and 44 km from Addison Road-Seat Pleasant, Unbelievable Beach Views For 6 offers air conditioning.

  • Located in North Beach, 700 metres from North Beach and 45 km from Addison Road-Seat Pleasant, Cozy Cottage 3 beds 2 baths W outdoor grill!

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Offering a fitness centre and city view, Huge Beach Bungalow- Yard, Beach Pass, King Beds is located in North Beach, 45 km from Addison Road-Seat Pleasant and 47 km from Annapolis Harbor.

    From US$438.62 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Located in North Beach, 1.7 km from North Beach and 46 km from Addison Road-Seat Pleasant, Bayfront Maryland Retreat with Deck, Near Beaches! offers air conditioning.

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 4 reviews

    Situated in North Beach and only 2 km from North Beach, Waterfront Lux Cottage With Amazing Views Near DC features accommodation with sea views, free WiFi and free private parking.

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 2 reviews

    Boasting air-conditioned accommodation with a patio, Updated North Beach Cottage Pet Friendly! is situated in Deale.

Save money on holiday homes in Chesapeake Beach and nearby – budget options available

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Situated in Deale, 45 km from Addison Road-Seat Pleasant and 45 km from Annapolis Harbor, Waterfront North Beach Home about 2 Mi to Beach! offers air conditioning.

  • Washington's Retreat

    Tracys Landing
    Budget options available

    Featuring private pool, Washington's Retreat is located on the beachfront in Tracys Landing. A hot tub is available for guests.

  • Located in Deale, 34 km from Annapolis Harbor and 40 km from Addison Road-Seat Pleasant, Water-View Deale Home Walk to Marina, Restaurants offers air conditioning.

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Hotels near FedEx Field

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Hotels in Chesapeake Beach

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Holiday Homes in Ocean City

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Hotels near Baltimore - Washington International Airport

Perfect for a late arrival or early departure.

Hotels near Washington Dulles International Airport

Got a stopover, late arrival or early departure? Find hotels conveniently close to the airport.

Holiday Homes in Annapolis

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Holiday Homes in Maryland

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