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Taylors Island Holiday Rentals

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50 rentals in Taylors Island.
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Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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A Vacation Away From It All-Family And Pet Friendly

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Little Farmhouse by the bay

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Tidal Serenity- Remote Waterfront Home with dock

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Family and Pet-Friendly, Waterfront with Pier

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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6.5 Acre Waterfront Family Retreat with Pool and Sandy Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Peaceful Multi-generational Waterfront Retreat w/Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SPECIAL RATES, Breathtaking Views, 450 pier, kayaks, fossils, priv beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Waterfront Rental on Fishing Creek, Cambridge, MD

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Harbor Cottage Vacation Rental

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Family Retreat with Deepwater Dock

Holiday Rental House
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 House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40

Holiday Rental House
12 bedrooms
9 bathrooms
Sleeps 40
Match: Sleeps
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Waterfront, 23 Private Acres, Dock & Pool

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Very Private 2 Acre Waterfront Family Retreat with Pool and Pier

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Our Always Dreaming Cottage - The Bay At Your Back Steps

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cedar Beach Lodge is a beautiful, comfy, all-season home on the Chesapeake Bay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Retreat on the Chesapeake

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Family Retreat with Pool on 7+ acres!

Holiday Rental House
10 bedrooms
7 bathrooms
Sleeps 24
Match: Sleeps
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Harwood Cottage on Church Creek, waterfront

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront Getaway on the Choptank River

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW VACATION HOME !!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cottage at Heron Cove, Chesapeake Bay, Cambridge

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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BayDreams - IronMan/Eagleman Retreat on the bay

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Year Round Estate on Bay / Fam. Reunions / Slps 28

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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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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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 House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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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 House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quarterdeck at Swan Cove Manor

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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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Best kept secret by the bay (Entire House)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Outrigger at Swan Cove Manor

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Hoopers Island Bayside Studio, 360 Degrees WATER VIEWS near IRONMAN Cambridge

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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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 House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Hudson Manor - Multi-Family Waterfront Compound, Pool, Beach Volleyball!

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
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Monasterevin - Spacious Waterfront Home on 110-Acre Estate, Pets Welcome!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Spring Is Here, Come Explore Fossils and One Mile of Beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Quiet cottage on wooded property

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Business or Leisure?

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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White Heron Inn 2565 Old House Point Rd

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront glass house with private beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Creek Gorgeous Private Home Awaits your arrival. This place has it all!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Breathtaking Waterfront Cambridge Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Mariner at Swan Cove Manor

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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