Vacation Rentals & Apartments in Chesapeake Beach

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Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,105

Bahia Breeze - Beachfront Cottage

Chesapeake Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$226

Great rentals within 20 miles that match your search

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$716

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$352

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

Price per night from

$487

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$476

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$859

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,117

One Beautiful home come relax

Cheltenham house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$201

Waterview Cottage In St. Michaels!

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Price per night from

$382

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$802

Annapolis Area Shagrila Resort

Davidsonville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$916

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$801

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$1,890

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$573

The Legends Getaway

Bryantown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$602

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

Price per night from

$2,290

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

  • 25 bedrooms
  • 25 bathrooms
  • sleeps 50

Price per night from

$7,443

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$400

Breathtaking Waterfront Cambridge Getaway

Cambridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$682

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,290

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,863

SeaGlass House by-the-Bay

Annapolis house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$670

Steps from the water, Easy parking and private backyard patio

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$355

Take your Leave of Absence around gardens with driveway parking

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$426

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$416

"Around the corner" from everything, private backyard and parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$384

Eastport Gem - Popular house walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$400

Cottage by the Bay on one level in family-friendly community

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$367

Eastport Bungalow - Popular house Walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$400

Pet-friendly Edgewater cottage with hot tub near waterfront!

Edgewater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$281

Price per night from

$637

Free Parking with private fenced-in backyard with pool table at Weekender

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$292

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$321

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$429

Price per night from

$403

Popular Eastport Retreat - private back patio with parking and walk to USNA

Annapolis house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Price per night from

$785

Quiet Cottage, Hot Tub, Bay View, Block to Beach, 1hr to DC

Saint Leonard house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$251

Viewing 38 of 66
rentals in Chesapeake Beach

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About Chesapeake Beach

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 vacation rental of your own. Vacation 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 vacation 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 vacation 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 vacation. 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 vacation rental close to your favorite activities. While you're visiting the Chesapeake Bay, consider taking a trip to Washington, D.C. or the Delaware Bay to the north.

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