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Saint Leonard Holiday Rentals

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50 rentals in Saint Leonard.
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Spring Is Here, Come Explore Fossils and One Mile of Beach, holiday rental in Saint Leonard

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Plantation Style Home on Patuxent River, holiday rental in Saint Leonard

Plantation Style Home on Patuxent River

7 bedrooms
7 bathrooms
Sleeps 16
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Family and Pet-Friendly, Waterfront with Pier, holiday rental in Saint Leonard

Family and Pet-Friendly, Waterfront with Pier

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Wildlife Retreat on the Patuxent River, holiday rental in Saint Leonard

Waterfront Wildlife Retreat on the Patuxent River

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay, holiday rental in Saint Leonard

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A waterfront vacation rental located on the Chesapeake Bay, holiday rental in Saint Leonard

A waterfront vacation rental located on the Chesapeake Bay

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!, holiday rental in Saint Leonard

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A Vacation Away From It All-Family And Pet Friendly, holiday rental in Saint Leonard

A Vacation Away From It All-Family And Pet Friendly

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock, holiday rental in Saint Leonard

Waterfront Family Retreat with Deepwater Dock

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL, holiday rental in Saint Leonard

BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Getaway on the Choptank River, holiday rental in Saint Leonard

Waterfront Getaway on the Choptank River

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Cottage Newly Renovated 2 Bed 2 Bath Sleeps 6 with an AMAZING Yard, holiday rental in Saint Leonard

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unbelievable Home Newly Renovated Sleeps Up to 9, holiday rental in Saint Leonard

Unbelievable Home Newly Renovated Sleeps Up to 9

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront, 23 Private Acres, Dock  & Pool, holiday rental in Saint Leonard

Waterfront, 23 Private Acres, Dock & Pool

4 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Waterfront Rental on Fishing Creek, Cambridge, MD, holiday rental in Saint Leonard

Waterfront Rental on Fishing Creek, Cambridge, MD

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, holiday rental in Saint Leonard

Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Spacious house with great deck close to boardwalk, shops, and restaurants., holiday rental in Saint Leonard

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

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront, Water All Around, Peaceful Family Getaway, holiday rental in Saint Leonard

Waterfront, Water All Around, Peaceful Family Getaway

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6, holiday rental in Saint Leonard

Lovely 3 bedroom 2 bath fully renovated cottage Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
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Sweet Spot Cottage on the Bay, holiday rental in Saint Leonard

Sweet Spot Cottage on the Bay

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Family Retreat with Pool on 7+ acres!, holiday rental in Saint Leonard

Waterfront Family Retreat with Pool on 7+ acres!

10 bedrooms
7 bathrooms
Sleeps 24
Match: Sleeps
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Crystal Cove Retreat, holiday rental in Saint Leonard

Crystal Cove Retreat

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Year Round Estate on Bay / Fam. Reunions / Slps 28, holiday rental in Saint Leonard

Year Round Estate on Bay / Fam. Reunions / Slps 28

7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, holiday rental in Saint Leonard

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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407 Southwinds - Renovated with Direct Chesapeake Bay View near DC and Annapolis, holiday rental in Saint Leonard

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Retreat on the Chesapeake, holiday rental in Saint Leonard

Waterfront Retreat on the Chesapeake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Little Farmhouse by the bay, holiday rental in Saint Leonard

Little Farmhouse by the bay

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cottage Located on the Patuxent River!, holiday rental in Saint Leonard

Cottage Located on the Patuxent River!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bayfront Home with Amazing Rooftop Deck!, holiday rental in Saint Leonard

Bayfront Home with Amazing Rooftop Deck!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, holiday rental in Saint Leonard

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

6 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Outrigger at Swan Cove Manor, holiday rental in Saint Leonard

Outrigger at Swan Cove Manor

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge, holiday rental in Saint Leonard

Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Waterfront Charleston Colonial, holiday rental in Saint Leonard

Waterfront Charleston Colonial

4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Chesapeake Bay Waterfront on Hoopers Island with Private Beach, holiday rental in Saint Leonard

Chesapeake Bay Waterfront on Hoopers Island with Private Beach

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Chesapeake Waterfront Retreat with Pool, holiday rental in Saint Leonard

Chesapeake Waterfront Retreat with Pool

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Birdwatcher's Water Retreat, holiday rental in Saint Leonard

Birdwatcher's Water Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, holiday rental in Saint Leonard

CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, holiday rental in Saint Leonard

Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Quiet cottage on wooded property, holiday rental in Saint Leonard

Quiet cottage on wooded property

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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St. Leonard Cottage w/Pool Overlooking Wells Cove!, holiday rental in Saint Leonard

St. Leonard Cottage w/Pool Overlooking Wells Cove!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Panoramic Views of Herrington Harbour on the Bay., holiday rental in Saint Leonard

Panoramic Views of Herrington Harbour on the Bay.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, holiday rental in Saint Leonard

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Business or Leisure?, holiday rental in Saint Leonard

Business or Leisure?

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Mariner at Swan Cove Manor, holiday rental in Saint Leonard

Mariner at Swan Cove Manor

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Quarterdeck at Swan Cove Manor, holiday rental in Saint Leonard

Quarterdeck at Swan Cove Manor

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Indoor pool and spa located in beautiful Southern Maryland woodlands, holiday rental in Saint Leonard

Indoor pool and spa located in beautiful Southern Maryland woodlands

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Mackall House - HUGE Private home! Sleeps 14! Two kitchens and game room!, holiday rental in Saint Leonard

The Mackall House - HUGE Private home! Sleeps 14! Two kitchens and game room!

6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, holiday rental in Saint Leonard

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Birdwatcher's Water Retreat, holiday rental in Saint Leonard

Birdwatcher's Water Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Waterfront Home w/ Dock, Kayaks, & Sailboat!, holiday rental in Saint Leonard

NEW! Waterfront Home w/ Dock, Kayaks, & Sailboat!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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