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Houses in Chesapeake Beach and Cottages – Holiday Lettings - Holiday Rentals Chesapeake Beach

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12 Holiday homes

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Home rental in Chesapeake Beach

Chesapeake Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £224 / night

£1,565 / week

1 / 30

Ski home to rent in Chesapeake Beach

Chesapeake Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £221 / night

£1,548 / week

1 / 17

Holiday cottage in Chesapeake Beach

Chesapeake Beach cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £106 / night

£741 / week

1 / 25

Holiday cottage in Chesapeake Beach

Chesapeake Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £152 / night

£1,060 / week

1 / 30

Holiday home in Chesapeake Beach

Chesapeake Beach house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £378 / night

£2,640 / week

1 / 30

Chesapeake Beach holiday home rental

Chesapeake Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £638 / night

£4,462 / week

1 / 29

Chesapeake Beach holiday home rental

Chesapeake Beach house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £287 / night

£2,004 / week

1 / 30

Chesapeake Beach holiday home rental

Chesapeake Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Pricing unknown

1 / 10

Holiday home rental

Chesapeake Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £361 / night

£2,525 / week

1 / 27

Holiday cottage in Chesapeake Beach

Chesapeake Beach cottage

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £319 / night

£2,229 / week

1 / 30

Holiday cottage in Chesapeake Beach

Chesapeake Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

from £160 / night

£1,120 / week

1 / 25

Home rental in Chesapeake Beach

Chesapeake Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from £202 / night

£1,411 / week

1 / 30

Great rentals within 20 miles that match your search

Port Republic holiday home rental

Port Republic house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 5

from £174 / night

£1,213 / week

1 / 30

Holiday home in Port Republic

Port Republic house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £182 / night

£1,268 / week

1 / 30

Holiday home in Bozman

Bozman house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

from £802 / night

£5,609 / week

1 / 30

Holiday home in Annapolis

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £421 / night

£2,948 / week

1 / 30

Home accommodation in Edgewater

Edgewater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £405 / night

£2,832 / week

1 / 30

Annapolis holiday home rental

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £702 / night

£4,912 / week

1 / 21

Annapolis ski apartment to rent.

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £145 / night

£1,016 / week

1 / 30

Ski home to rent in Neavitt

Neavitt house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £302 / night

£2,113 / week

1 / 16

Holiday cottage rental

Deale cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £247 / night

£1,729 / week

1 / 30

Cottage rental in Bozman

Bozman cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £250 / night

£1,746 / week

1 / 30

Cottage rental in St. Michaels

St. Michaels cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £198 / night

£1,383 / week

1 / 23

Ski home to rent in Cambridge

Cambridge house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 15

from £399 / night

£2,794 / week

1 / 27

Holiday cottage rental

St. Michaels cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £225 / night

£1,570 / week

1 / 23

Taylors Island ski home to rent.

Taylors Island house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 14

from £435 / night

£3,041 / week

1 / 30

Holiday home in Tracys Landing

Tracys Landing house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 20

from £1,071 / night

£7,497 / week

1 / 30

Ski home to rent in Annapolis

Annapolis house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £470 / night

£3,288 / week

1 / 30

Home rental in St. Michaels

St. Michaels house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £508 / night

£3,557 / week

1 / 30

Riva holiday apartment rental

Riva apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £115 / night

£802 / week

1 / 24

Annapolis holiday home rental

Annapolis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £159 / night

£1,109 / week

1 / 19

Holiday home in Riva

Riva house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 12

from £658 / night

£4,605 / week

1 / 30

Annapolis holiday home rental

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £314 / night

£2,196 / week

1 / 30

Ski home to rent in Harwood

Harwood house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

from £668 / night

£4,671 / week

1 / 30

Home rental in St. Michaels

St. Michaels house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 8

from £715 / night

£5,000 / week

1 / 30

Holiday home in Stevensville

Stevensville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

from £564 / night

£3,946 / week

1 / 30

Holiday home in Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £385 / night

£2,695 / week

1 / 29

Holiday home in Riva

Riva house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £149 / night

£1,038 / week

1 / 28

Sherwood holiday cottage rental

Sherwood cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £138 / night

£966 / week

1 / 20

Holiday villa in Romancoke

Romancoke villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from £419 / night

£2,931 / week

1 / 28

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Chesapeake Beach holidays

The Chesapeake Bay region extends many miles into inland Maryland from the Atlantic Coast and is made up of all the towns that lie along the bay and its rivers and waterways. The towns in this area are diverse, but share a unique culture and centuries-old maritime history. The towns and metropolitan areas also share the bay itself and the natural beauty and riches that it offers, including the famous blue crab. Come to the Chesapeake Bay to experience cultural traditions, great museums, shipyards, and lighthouses. And while you're here, stay in a holiday rental of your own. holiday rentals in this area are often less expensive than hotels. They are also more spacious and have better amenities, allowing you to relax in style as you plan your holiday adventures.

Wake up each morning in your bayside cottage or villa and enjoy a leisurely breakfast as birds call out from the delicate Chesapeake wetlands and marshes. Then head downtown to explore the shopping and historic strolling areas, go fishing, clamming or tide pooling in the bay, or relax on a pebbly beach. In the afternoon go for a hike or play a round of Chesapeake Bay golf. After a long day of exploring, head home to your holiday rental and host dinner for your friends and family on your rental's deck or light a fire and enjoy a night of Chesapeake Bay camping under the stars.

Here are a few additional suggestions:

  • Experience Chesapeake Bay sailing: Let the wind fill your sails and carry you out onto the waters of the bay in an authentic Chesapeake Bay Skipjack.
  • Enjoy a blue crab feast: Stop at a crab shack anywhere along the bay and bring home a barrel of real live blue crabs ready for steaming.
  • Go for a hike: Chesapeake Bay camping areas and hiking trails wind through the bluffs and sandy pine forest and offer beautiful views and great opportunities for bird watching.
  • Relax in a Chesapeake Bay spa: The spas in this area are legendary, and offer a perfect place to indulge in an afternoon of head-to-toe pampering.
  • Rent a bicycle: Pack a picnic lunch, rent a bicycle in town, and pedal along the boardwalk or through one of the rolling green parks around the bay area.
  • Tour a historic home: Almost every town along the bay can boast of streets and homes that have stood for centuries.
  • Explore a historic lighthouse: Preserved historic lighthouses, active working lighthouses, and lighthouse museums are a very important part of Chesapeake Bay history and culture.

The Chesapeake Bay is the perfect destination for history lovers, nature lovers, and those looking to take a romantic getaway or a unique family holiday. You'll never run out of fun things to do here, and the area is beautiful during all four seasons of the year. Get the most out of your visit by finding a holiday rental close to your favourite activities. While you're visiting the Chesapeake Bay, consider taking a trip to Washington, D.C. or the Delaware Bay to the north.

Also consider