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Saint Leonard Holiday Apartments

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50 rentals in Saint Leonard.
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Chesapeake Bay Harbor Cottage Vacation Rental, holiday rental in Saint Leonard
Chesapeake Bay Harbor Cottage Vacation Rental, holiday rental in Saint Leonard
Chesapeake Bay Harbor Cottage Vacation Rental, holiday rental in Saint Leonard

Chesapeake Bay Harbor Cottage Vacation Rental

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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NEW VACATION HOME !!!!, holiday rental in Saint Leonard
NEW VACATION HOME !!!!, holiday rental in Saint Leonard
NEW VACATION HOME !!!!, holiday rental in Saint Leonard

NEW VACATION HOME !!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Plantation Style Home on Patuxent River, holiday rental in Saint Leonard
Plantation Style Home on Patuxent River, holiday rental in Saint Leonard
Plantation Style Home on Patuxent River, holiday rental in Saint Leonard

Plantation Style Home on Patuxent River

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
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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, holiday rental in Saint Leonard
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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Family and Pet-Friendly, Waterfront with Pier, holiday rental in Saint Leonard
Family and Pet-Friendly, Waterfront with Pier, holiday rental in Saint Leonard
Family and Pet-Friendly, Waterfront with Pier, holiday rental in Saint Leonard

Family and Pet-Friendly, Waterfront with Pier

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Waterfront Wildlife Retreat on the Patuxent River, holiday rental in Saint Leonard
Waterfront Wildlife Retreat on the Patuxent River, holiday rental in Saint Leonard
Waterfront Wildlife Retreat on the Patuxent River, holiday rental in Saint Leonard

Waterfront Wildlife Retreat on the Patuxent River

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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, holiday rental in Saint Leonard
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath, holiday rental in Saint Leonard
Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath, holiday rental in Saint Leonard
Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath, holiday rental in Saint Leonard

Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach, holiday rental in Saint Leonard
SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach, holiday rental in Saint Leonard
SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach, holiday rental in Saint Leonard

SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!, holiday rental in Saint Leonard
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!, holiday rental in Saint Leonard
Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!, holiday rental in Saint Leonard

Newly Renovated Secluded Luxury waterfront cottage with private deep water pier!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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, holiday rental in Saint Leonard
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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
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Waterfront Family Retreat with Deepwater Dock, holiday rental in Saint Leonard
Waterfront Family Retreat with Deepwater Dock, holiday rental in Saint Leonard
Waterfront Family Retreat with Deepwater Dock, holiday rental in Saint Leonard

Waterfront Family Retreat with Deepwater Dock

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 15
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BeachWalk Cottage  - Charm by the Chesapeake Bay., holiday rental in Saint Leonard
BeachWalk Cottage  - Charm by the Chesapeake Bay., holiday rental in Saint Leonard
BeachWalk Cottage  - Charm by the Chesapeake Bay., holiday rental in Saint Leonard

BeachWalk Cottage - Charm by the Chesapeake Bay.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, holiday rental in Saint Leonard
5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, holiday rental in Saint Leonard
5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, holiday rental in Saint Leonard

5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40

Holiday Rental House
12 bedrooms
9 bathrooms
Sleeps 40
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Our Always Dreaming Cottage - The Bay At Your Back Steps, holiday rental in Saint Leonard
Our Always Dreaming Cottage - The Bay At Your Back Steps, holiday rental in Saint Leonard
Our Always Dreaming Cottage - The Bay At Your Back Steps, holiday rental in Saint Leonard

Our Always Dreaming Cottage - The Bay At Your Back Steps

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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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, holiday rental in Saint Leonard
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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 14
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Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay, holiday rental in Saint Leonard
Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay, holiday rental in Saint Leonard
Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay, holiday rental in Saint Leonard

Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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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, holiday rental in Saint Leonard
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Bayfront Home with Amazing Rooftop Deck!, holiday rental in Saint Leonard
Bayfront Home with Amazing Rooftop Deck!, holiday rental in Saint Leonard
Bayfront Home with Amazing Rooftop Deck!, holiday rental in Saint Leonard

Bayfront Home with Amazing Rooftop Deck!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 15
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, holiday rental in Saint Leonard
Unbelievable Home Newly Renovated Sleeps Up to 9, holiday rental in Saint Leonard

Unbelievable Home Newly Renovated Sleeps Up to 9

Holiday Rental House
3 bedrooms
3 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!, holiday rental in Saint Leonard
Cottage Located on the Patuxent River!, holiday rental in Saint Leonard

Cottage Located on the Patuxent River!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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, holiday rental in Saint Leonard
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Crystal Cove Retreat, holiday rental in Saint Leonard
Crystal Cove Retreat, holiday rental in Saint Leonard
Crystal Cove Retreat, holiday rental in Saint Leonard

Crystal Cove Retreat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BayDreams - IronMan/Eagleman Retreat on the bay, holiday rental in Saint Leonard
BayDreams - IronMan/Eagleman Retreat on the bay, holiday rental in Saint Leonard
BayDreams - IronMan/Eagleman Retreat on the bay, holiday rental in Saint Leonard

BayDreams - IronMan/Eagleman Retreat on the bay

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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, holiday rental in Saint Leonard
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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Waterfront Charleston Colonial, holiday rental in Saint Leonard
Waterfront Charleston Colonial, holiday rental in Saint Leonard
Waterfront Charleston Colonial, holiday rental in Saint Leonard

Waterfront Charleston Colonial

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Quiet Woodland cottage near St. Leonard's Creek, holiday rental in Saint Leonard
Quiet Woodland cottage near St. Leonard's Creek, holiday rental in Saint Leonard
Quiet Woodland cottage near St. Leonard's Creek, holiday rental in Saint Leonard

Quiet Woodland cottage near St. Leonard's Creek

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Chesapeake Waterfront Retreat with Pool, holiday rental in Saint Leonard
Chesapeake Waterfront Retreat with Pool, holiday rental in Saint Leonard
Chesapeake Waterfront Retreat with Pool, holiday rental in Saint Leonard

Chesapeake Waterfront Retreat with Pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Private Beachfront Home with Beautiful Bay View

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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!, holiday rental in Saint Leonard
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!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 15
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Charming and Cozy with a Waterview, holiday rental in Saint Leonard
Charming and Cozy with a Waterview, holiday rental in Saint Leonard
Charming and Cozy with a Waterview, holiday rental in Saint Leonard

Charming and Cozy with a Waterview

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bay Water Cottage - Private Bayfront Retreat from the World!, holiday rental in Saint Leonard
Bay Water Cottage - Private Bayfront Retreat from the World!, holiday rental in Saint Leonard
Bay Water Cottage - Private Bayfront Retreat from the World!, holiday rental in Saint Leonard

Bay Water Cottage - Private Bayfront Retreat from the World!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quarterdeck at Swan Cove Manor, holiday rental in Saint Leonard
Quarterdeck at Swan Cove Manor, holiday rental in Saint Leonard
Quarterdeck at Swan Cove Manor, holiday rental in Saint Leonard

Quarterdeck at Swan Cove Manor

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tidal Serenity- Remote Waterfront Home with dock, holiday rental in Saint Leonard
Tidal Serenity- Remote Waterfront Home with dock, holiday rental in Saint Leonard
Tidal Serenity- Remote Waterfront Home with dock, holiday rental in Saint Leonard

Tidal Serenity- Remote Waterfront Home with dock

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!, holiday rental in Saint Leonard
The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!, holiday rental in Saint Leonard
The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!, holiday rental in Saint Leonard

The Bird's Nest - Huge Waterfront Home, Pool, Yard, Sleeps 16, Pets Welcome!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Indoor pool and spa in contemporary French home secluded in surrounding woods, holiday rental in Saint Leonard
Indoor pool and spa in contemporary French home secluded in surrounding woods, holiday rental in Saint Leonard
Indoor pool and spa in contemporary French home secluded in surrounding woods, holiday rental in Saint Leonard

Indoor pool and spa in contemporary French home secluded in surrounding woods

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Modern Waterfront Home, Great views, Sauna, Jacuzzi, 1Hr to DC, holiday rental in Saint Leonard
Modern Waterfront Home, Great views, Sauna, Jacuzzi, 1Hr to DC, holiday rental in Saint Leonard
Modern Waterfront Home, Great views, Sauna, Jacuzzi, 1Hr to DC, holiday rental in Saint Leonard

Modern Waterfront Home, Great views, Sauna, Jacuzzi, 1Hr to DC

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!, holiday rental in Saint Leonard
Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!, holiday rental in Saint Leonard
Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!, holiday rental in Saint Leonard

Willoughby - Over 10,000 SqFt, Indoor Pool, Grill, Sleeps 24!

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 24
Match: Sleeps
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Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, holiday rental in Saint Leonard
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, holiday rental in Saint Leonard
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, holiday rental in Saint Leonard

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS., holiday rental in Saint Leonard
AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS., holiday rental in Saint Leonard
AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS., holiday rental in Saint Leonard

AMAZING WATERFRONT DESTINATION FOR ROMANTIC AND FAMILY VACATIONS.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
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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, holiday rental in Saint Leonard
NEW! Coastal Pet-Friendly Cottage <½ Mi to Beaches, holiday rental in Saint Leonard

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beach Home Away from Home Near Beaches & Popular Hangouts, holiday rental in Saint Leonard
Beach Home Away from Home Near Beaches & Popular Hangouts, holiday rental in Saint Leonard
Beach Home Away from Home Near Beaches & Popular Hangouts, holiday rental in Saint Leonard

Beach Home Away from Home Near Beaches & Popular Hangouts

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quiet cottage on wooded property, holiday rental in Saint Leonard
Quiet cottage on wooded property, holiday rental in Saint Leonard
Quiet cottage on wooded property, holiday rental in Saint Leonard

Quiet cottage on wooded property

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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!, holiday rental in Saint Leonard
Chesapeake Beach Apt. Walk to Bay, Beach & Marina!, holiday rental in Saint Leonard

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

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

Business or Leisure?

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Panoramic River Views , Jacuzzi, Sauna- Waterfront Modern Home 1 Hr to D.C., holiday rental in Saint Leonard
Panoramic River Views , Jacuzzi, Sauna- Waterfront Modern Home 1 Hr to D.C., holiday rental in Saint Leonard
Panoramic River Views , Jacuzzi, Sauna- Waterfront Modern Home 1 Hr to D.C., holiday rental in Saint Leonard

Panoramic River Views , Jacuzzi, Sauna- Waterfront Modern Home 1 Hr to D.C.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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, holiday rental in Saint Leonard
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront glass house with private beach, holiday rental in Saint Leonard
Waterfront glass house with private beach, holiday rental in Saint Leonard
Waterfront glass house with private beach, holiday rental in Saint Leonard

Waterfront glass house with private beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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BYOB Bring Your Own Bikes!!, holiday rental in Saint Leonard
BYOB Bring Your Own Bikes!!, holiday rental in Saint Leonard
BYOB Bring Your Own Bikes!!, holiday rental in Saint Leonard

BYOB Bring Your Own Bikes!!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Delightful Pet Friendly Family Home In Great Location, holiday rental in Saint Leonard
Delightful Pet Friendly Family Home In Great Location, holiday rental in Saint Leonard
Delightful Pet Friendly Family Home In Great Location, holiday rental in Saint Leonard

Delightful Pet Friendly Family Home In Great Location

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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