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Chesapeake Beach Holiday Rentals

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50 rentals in Chesapeake Beach.
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Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, holiday rental in Chesapeake Beach

Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard

2 bedrooms
2 bathrooms
Sleeps 6
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Unbelievable Home Newly Renovated Sleeps Up to 9, holiday rental in Chesapeake Beach

Unbelievable Home Newly Renovated Sleeps Up to 9

3 bedrooms
3 bathrooms
Sleeps 9
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NEW! Waterfront Home w/ Rowboat, Kayaks & Fishing, holiday rental in Chesapeake Beach

NEW! Waterfront Home w/ Rowboat, Kayaks & Fishing

2 bedrooms
2 bathrooms
Sleeps 4
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Indoor pool and spa located in beautiful Southern Maryland woodlands, holiday rental in Chesapeake Beach

Indoor pool and spa located in beautiful Southern Maryland woodlands

3 bedrooms
3 bathrooms
Sleeps 8
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Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, holiday rental in Chesapeake Beach

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), holiday rental in Chesapeake Beach

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

7 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, holiday rental in Chesapeake Beach

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

3 bedrooms
2 bathrooms
Sleeps 11
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Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay, holiday rental in Chesapeake Beach

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, holiday rental in Chesapeake Beach

Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, holiday rental in Chesapeake Beach

Comfy home on beautiful Leadenham Creek. Book now for summer!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Spacious house with great deck close to boardwalk, shops, and restaurants., holiday rental in Chesapeake Beach

Spacious house with great deck close to boardwalk, shops, and restaurants.

3 bedrooms
3 bathrooms
Sleeps 9
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Chesapeake Bay Cottage, holiday rental in Chesapeake Beach

Chesapeake Bay Cottage

3 bedrooms
2 bathrooms
Sleeps 8
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Fully remodel 2 bedroom country cottage., holiday rental in Chesapeake Beach

Fully remodel 2 bedroom country cottage.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Chesapeake Beach

Charming 3 Bedroom 3 Bath Beach Front Property

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage by the Beach, holiday rental in Chesapeake Beach

Cozy Cottage by the Beach

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Views of the Bay - Waterfront, holiday rental in Chesapeake Beach

Stunning Views of the Bay - Waterfront

3 bedrooms
4 bathrooms
Sleeps 10
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The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples, holiday rental in Chesapeake Beach

The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples

3 bedrooms
2 bathrooms
Sleeps 8
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Relax in Tilghman Island, holiday rental in Chesapeake Beach

Relax in Tilghman Island

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, holiday rental in Chesapeake Beach

Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WATERFRONT - DRIFTWOOD LODGE, holiday rental in Chesapeake Beach

WATERFRONT - DRIFTWOOD LODGE

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Holidays at the Cove  - plenty of space to gather while making memories, holiday rental in Chesapeake Beach

Holidays at the Cove - plenty of space to gather while making memories

5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront, Water All Around, Peaceful Family Getaway, holiday rental in Chesapeake Beach

Waterfront, Water All Around, Peaceful Family Getaway

3 bedrooms
2 bathrooms
Sleeps 6
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New Modern Waterfront Farmhouse Built 2018, holiday rental in Chesapeake Beach

New Modern Waterfront Farmhouse Built 2018

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks, holiday rental in Chesapeake Beach

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, holiday rental in Chesapeake Beach

407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, holiday rental in Chesapeake Beach

Eastern Shore Getaway Near St. Michaels

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in Chesapeake Beach

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bayfront Home with Amazing Rooftop Deck!, holiday rental in Chesapeake Beach

Bayfront Home with Amazing Rooftop Deck!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Cottage Located on the Patuxent River!, holiday rental in Chesapeake Beach

Cottage Located on the Patuxent River!

1 bedroom
1 bathroom
Sleeps 2
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Crystal Cove Retreat, holiday rental in Chesapeake Beach

Crystal Cove Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sweet Spot Cottage on the Bay, holiday rental in Chesapeake Beach

Sweet Spot Cottage on the Bay

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Main House at Grandview at Pleasure Point, holiday rental in Chesapeake Beach

Main House at Grandview at Pleasure Point

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Adorable waterside cottage with pool Beach community, holiday rental in Chesapeake Beach

Adorable waterside cottage with pool Beach community

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Not to early to think about joining us this Spring and Summer., holiday rental in Chesapeake Beach

Not to early to think about joining us this Spring and Summer.

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Chesapeake Beach

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Sandy Pines:  Enjoy Harris Creek w/Pool and Boats, holiday rental in Chesapeake Beach

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all.  3 sides of, holiday rental in Chesapeake Beach

UNFORGETTABLE FAMILY GETAWAY. This fully renovated home has it all. 3 sides of

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Chesapeake Waterfront Flat Just 26 Mi to DC, holiday rental in Chesapeake Beach

Lovely Chesapeake Waterfront Flat Just 26 Mi to DC

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Spring Is Here, Come Explore Fossils and One Mile of Beach, holiday rental in Chesapeake Beach

Spring Is Here, Come Explore Fossils and One Mile of Beach

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cottage 2 at Grandview Pleasure Point, holiday rental in Chesapeake Beach

Cottage 2 at Grandview Pleasure Point

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!, holiday rental in Chesapeake Beach

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview, holiday rental in Chesapeake Beach

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Cottage 1a at Grandview Pleasure Point, holiday rental in Chesapeake Beach

Cottage 1a at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage 1b at Grandview Pleasure Point, holiday rental in Chesapeake Beach

Cottage 1b at Grandview Pleasure Point

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, holiday rental in Chesapeake Beach

St. Michaels Area Cottage - Walk to Water & Marina

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Annapolis Waterview home, holiday rental in Chesapeake Beach

Charming Annapolis Waterview home

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, holiday rental in Chesapeake Beach

NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!, holiday rental in Chesapeake Beach

NEW! Secluded Farmhouse on 45 Acres w/ Fire Pit!

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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The Legends Getaway, holiday rental in Chesapeake Beach

The Legends Getaway

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Chesapeake Bay Getaway™ | Waterfront Experience with Pier!, holiday rental in Chesapeake Beach

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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