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Taylors Island Vacation Rentals

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5 mi
50 rentals in Taylors Island.
Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, vacation rental in Taylors Island
Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, vacation rental in Taylors Island
Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island, vacation rental in Taylors Island

Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island

Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Vacation Rental on Taylor’s Island w/ Private Dock, vacation rental in Taylors Island
Vacation Rental on Taylor’s Island w/ Private Dock, vacation rental in Taylors Island
Vacation Rental on Taylor’s Island w/ Private Dock, vacation rental in Taylors Island

Vacation Rental on Taylor’s Island w/ Private Dock

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Bayfront Gem w/ Amazing Water Views + Pond!, vacation rental in Taylors Island
Bayfront Gem w/ Amazing Water Views + Pond!, vacation rental in Taylors Island
Bayfront Gem w/ Amazing Water Views + Pond!, vacation rental in Taylors Island

Bayfront Gem w/ Amazing Water Views + Pond!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tidal Serenity- Remote Waterfront Home with dock, vacation rental in Taylors Island
Tidal Serenity- Remote Waterfront Home with dock, vacation rental in Taylors Island
Tidal Serenity- Remote Waterfront Home with dock, vacation rental in Taylors Island

Tidal Serenity- Remote Waterfront Home with dock

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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A Vacation Away From It All-Family And Pet Friendly, vacation rental in Taylors Island
A Vacation Away From It All-Family And Pet Friendly, vacation rental in Taylors Island
A Vacation Away From It All-Family And Pet Friendly, vacation rental in Taylors Island

A Vacation Away From It All-Family And Pet Friendly

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront Nature/Outdoor Lovers Secluded Estate, vacation rental in Taylors Island
Waterfront Nature/Outdoor Lovers Secluded Estate, vacation rental in Taylors Island
Waterfront Nature/Outdoor Lovers Secluded Estate, vacation rental in Taylors Island

Waterfront Nature/Outdoor Lovers Secluded Estate

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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The following properties within 20 miles of Taylors Island match all your filters:
Beautiful Waterfront Retreat in Cambridge!, vacation rental in Taylors Island
Beautiful Waterfront Retreat in Cambridge!, vacation rental in Taylors Island
Beautiful Waterfront Retreat in Cambridge!, vacation rental in Taylors Island

Beautiful Waterfront Retreat in Cambridge!

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, vacation rental in Taylors Island
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, vacation rental in Taylors Island
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, vacation rental in Taylors Island

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Rental Home
7 bedrooms
6 bathrooms
Sleeps 27
Match: Sleeps
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Waterfront Family Retreat with Pool on 7+ acres!, vacation rental in Taylors Island
Waterfront Family Retreat with Pool on 7+ acres!, vacation rental in Taylors Island
Waterfront Family Retreat with Pool on 7+ acres!, vacation rental in Taylors Island

Waterfront Family Retreat with Pool on 7+ acres!

Rental Home
10 bedrooms
6 bathrooms
Sleeps 24
Match: Sleeps
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Family and Pet-Friendly, Waterfront with Pier, vacation rental in Taylors Island
Family and Pet-Friendly, Waterfront with Pier, vacation rental in Taylors Island
Family and Pet-Friendly, Waterfront with Pier, vacation rental in Taylors Island

Family and Pet-Friendly, Waterfront with Pier

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, vacation rental in Taylors Island
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, vacation rental in Taylors Island
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, vacation rental in Taylors Island

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Rental Home
6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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The Cedar Beach Lodge, vacation rental in Taylors Island
The Cedar Beach Lodge, vacation rental in Taylors Island
The Cedar Beach Lodge, vacation rental in Taylors Island

The Cedar Beach Lodge

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Getaway with Dock, vacation rental in Taylors Island
Waterfront Getaway with Dock, vacation rental in Taylors Island
Waterfront Getaway with Dock, vacation rental in Taylors Island

Waterfront Getaway with Dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront lighthouse styled retreat with breathtaking sunset and water views., vacation rental in Taylors Island
Waterfront lighthouse styled retreat with breathtaking sunset and water views., vacation rental in Taylors Island
Waterfront lighthouse styled retreat with breathtaking sunset and water views., vacation rental in Taylors Island

Waterfront lighthouse styled retreat with breathtaking sunset and water views.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, vacation rental in Taylors Island
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, vacation rental in Taylors Island
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, vacation rental in Taylors Island

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Rental Home
4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Waterfront cabin with incredible sunsets on Maryland's Eastern Shore., vacation rental in Taylors Island
Waterfront cabin with incredible sunsets on Maryland's Eastern Shore., vacation rental in Taylors Island
Waterfront cabin with incredible sunsets on Maryland's Eastern Shore., vacation rental in Taylors Island

Waterfront cabin with incredible sunsets on Maryland's Eastern Shore.

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate, vacation rental in Taylors Island
Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate, vacation rental in Taylors Island
Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate, vacation rental in Taylors Island

Weddings/Reunions/Corp & Private Retreats 22 Acre Chesapeake Waterfront Estate

Rental Home
20 bedrooms
17 bathrooms
Sleeps 20
Match: Sleeps
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Waterfront Getaway for Two, vacation rental in Taylors Island
Waterfront Getaway for Two, vacation rental in Taylors Island
Waterfront Getaway for Two, vacation rental in Taylors Island

Waterfront Getaway for Two

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quarterdeck at Swan Cove Manor, vacation rental in Taylors Island
Quarterdeck at Swan Cove Manor, vacation rental in Taylors Island
Quarterdeck at Swan Cove Manor, vacation rental in Taylors Island

Quarterdeck at Swan Cove Manor

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy apt located at a nonprofit animal sanctuary. Come visit!, vacation rental in Taylors Island
Comfy apt located at a nonprofit animal sanctuary. Come visit!, vacation rental in Taylors Island
Comfy apt located at a nonprofit animal sanctuary. Come visit!, vacation rental in Taylors Island

Comfy apt located at a nonprofit animal sanctuary. Come visit!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Private waterfront cottage with pool on Church Creek, vacation rental in Taylors Island
Private waterfront cottage with pool on Church Creek, vacation rental in Taylors Island
Private waterfront cottage with pool on Church Creek, vacation rental in Taylors Island

Private waterfront cottage with pool on Church Creek

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Waterfront property with private boat ramp and new dock!, vacation rental in Taylors Island
Waterfront property with private boat ramp and new dock!, vacation rental in Taylors Island
Waterfront property with private boat ramp and new dock!, vacation rental in Taylors Island

Waterfront property with private boat ramp and new dock!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!, vacation rental in Taylors Island
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!, vacation rental in Taylors Island
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!, vacation rental in Taylors Island

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. �, vacation rental in Taylors Island
Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. �, vacation rental in Taylors Island
Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. �, vacation rental in Taylors Island

Historic Farmhouse on the Chesapeake Bay! PANORAMIC Waterfront Sunsets. �

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!, vacation rental in Taylors Island
New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!, vacation rental in Taylors Island
New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!, vacation rental in Taylors Island

New Waterfront! Drop Anchor on Brannocks Bay. An Amazing waterfront retreat!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Outrigger at Swan Cove Manor, vacation rental in Taylors Island
Outrigger at Swan Cove Manor, vacation rental in Taylors Island
Outrigger at Swan Cove Manor, vacation rental in Taylors Island

Outrigger at Swan Cove Manor

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Chesapeake Waterfront with Private Beach & Pool, vacation rental in Taylors Island
Chesapeake Waterfront with Private Beach & Pool, vacation rental in Taylors Island
Chesapeake Waterfront with Private Beach & Pool, vacation rental in Taylors Island

Chesapeake Waterfront with Private Beach & Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Magnificent Madison's private bay getaway home!!, vacation rental in Taylors Island
Magnificent Madison's private bay getaway home!!, vacation rental in Taylors Island
Magnificent Madison's private bay getaway home!!, vacation rental in Taylors Island

Magnificent Madison's private bay getaway home!!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Endless Summer - Fun for the entire family!, vacation rental in Taylors Island
Endless Summer - Fun for the entire family!, vacation rental in Taylors Island
Endless Summer - Fun for the entire family!, vacation rental in Taylors Island

Endless Summer - Fun for the entire family!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Sunsets on the Bay, vacation rental in Taylors Island
Stunning Sunsets on the Bay, vacation rental in Taylors Island
Stunning Sunsets on the Bay, vacation rental in Taylors Island

Stunning Sunsets on the Bay

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BayDreams - IronMan/Eagleman Retreat on the bay, vacation rental in Taylors Island
BayDreams - IronMan/Eagleman Retreat on the bay, vacation rental in Taylors Island
BayDreams - IronMan/Eagleman Retreat on the bay, vacation rental in Taylors Island

BayDreams - IronMan/Eagleman Retreat on the bay

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mariner at Swan Cove Manor, vacation rental in Taylors Island
Mariner at Swan Cove Manor, vacation rental in Taylors Island
Mariner at Swan Cove Manor, vacation rental in Taylors Island

Mariner at Swan Cove Manor

Rental Home
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Taylors Island
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Taylors Island
Waterfront 5BR/3.5BA with private pool, dock, fire pit, kayaks, beach Sleeps 18, vacation rental in Taylors Island

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool, vacation rental in Taylors Island
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool, vacation rental in Taylors Island
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool, vacation rental in Taylors Island

Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool

Rental Home
4 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Taylors Island
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Taylors Island
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16, vacation rental in Taylors Island

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, vacation rental in Taylors Island
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, vacation rental in Taylors Island
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, vacation rental in Taylors Island

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront retreat with heated pool, historic guest house., vacation rental in Taylors Island
Waterfront retreat with heated pool, historic guest house., vacation rental in Taylors Island
Waterfront retreat with heated pool, historic guest house., vacation rental in Taylors Island

Waterfront retreat with heated pool, historic guest house.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Private 9 acre Family Retreat on the Chesapeake Bay, vacation rental in Taylors Island
Private 9 acre Family Retreat on the Chesapeake Bay, vacation rental in Taylors Island
Private 9 acre Family Retreat on the Chesapeake Bay, vacation rental in Taylors Island

Private 9 acre Family Retreat on the Chesapeake Bay

Rental Home
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier, vacation rental in Taylors Island
Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier, vacation rental in Taylors Island
Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier, vacation rental in Taylors Island

Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier

Rental Home
6 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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A Beautiful Waterfront Retreat for Family Gatherings!, vacation rental in Taylors Island
A Beautiful Waterfront Retreat for Family Gatherings!, vacation rental in Taylors Island
A Beautiful Waterfront Retreat for Family Gatherings!, vacation rental in Taylors Island

A Beautiful Waterfront Retreat for Family Gatherings!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Remarkable waterfront property on 270 acres, vacation rental in Taylors Island
Remarkable waterfront property on 270 acres, vacation rental in Taylors Island
Remarkable waterfront property on 270 acres, vacation rental in Taylors Island

Remarkable waterfront property on 270 acres

Rental Home
5 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Oyster Haven - Looking for that “shore” lifestyle?, vacation rental in Taylors Island
Oyster Haven - Looking for that “shore” lifestyle?, vacation rental in Taylors Island
Oyster Haven - Looking for that “shore” lifestyle?, vacation rental in Taylors Island

Oyster Haven - Looking for that “shore” lifestyle?

Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Family Waterfront- Beach, Pool, Pets, Dock - Chesapeake Escape , 7bd/5ba, vacation rental in Taylors Island
Family Waterfront- Beach, Pool, Pets, Dock - Chesapeake Escape , 7bd/5ba, vacation rental in Taylors Island
Family Waterfront- Beach, Pool, Pets, Dock - Chesapeake Escape , 7bd/5ba, vacation rental in Taylors Island

Family Waterfront- Beach, Pool, Pets, Dock - Chesapeake Escape , 7bd/5ba

Rental Home
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Bayberry Cove | Cozy Yet Spacious Waterfront Getaway!, vacation rental in Taylors Island
Bayberry Cove | Cozy Yet Spacious Waterfront Getaway!, vacation rental in Taylors Island
Bayberry Cove | Cozy Yet Spacious Waterfront Getaway!, vacation rental in Taylors Island

Bayberry Cove | Cozy Yet Spacious Waterfront Getaway!

Rental Home
7 bedrooms
7 bathrooms
Sleeps 17
Match: Sleeps
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Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, vacation rental in Taylors Island
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, vacation rental in Taylors Island
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28, vacation rental in Taylors Island

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Rental Home
7 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, vacation rental in Taylors Island
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, vacation rental in Taylors Island
Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths, vacation rental in Taylors Island

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

Rental Home
6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Private 2 Acre Waterfront Family Retreat with Pool & Pier, vacation rental in Taylors Island
Private 2 Acre Waterfront Family Retreat with Pool & Pier, vacation rental in Taylors Island
Private 2 Acre Waterfront Family Retreat with Pool & Pier, vacation rental in Taylors Island

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Rental Home
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16, vacation rental in Taylors Island
Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16, vacation rental in Taylors Island
Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16, vacation rental in Taylors Island

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Rental Home
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, vacation rental in Taylors Island
5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, vacation rental in Taylors Island
5*Chesapeake Bay Waterfront Estate Vacation/Reunions/Wedding/Corporate Sleeps 40, vacation rental in Taylors Island

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

Rental Home
12 bedrooms
9 bathrooms
Sleeps 40
Match: Sleeps
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Blackwater Refuge Lodge, vacation rental in Taylors Island
Blackwater Refuge Lodge, vacation rental in Taylors Island
Blackwater Refuge Lodge, vacation rental in Taylors Island

Blackwater Refuge Lodge

Rental Home
8 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Taylors Island