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Taylors Island Vacation Rentals

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5 km
47 rentals in Taylors Island.
Private Waterfront Family Retreat w/ Pool Pickleball Basketball and Volleyball, vacation rental in Taylors Island
Private Waterfront Family Retreat w/ Pool Pickleball Basketball and Volleyball, vacation rental in Taylors Island
Private Waterfront Family Retreat w/ Pool Pickleball Basketball and Volleyball, vacation rental in Taylors Island

Private Waterfront Family Retreat w/ Pool Pickleball Basketball and Volleyball

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 14
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Bay Views & Fire Pit: Taylor’s Island Retreat, vacation rental in Taylors Island
Bay Views & Fire Pit: Taylor’s Island Retreat, vacation rental in Taylors Island
Bay Views & Fire Pit: Taylor’s Island Retreat, vacation rental in Taylors Island

Bay Views & Fire Pit: Taylor’s Island Retreat

Holiday Rental House
7 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!

Holiday Rental House
5 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

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!, vacation rental in Taylors Island
About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!, vacation rental in Taylors Island
About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!, vacation rental in Taylors Island

About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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The following properties within 32 kms of Taylors Island match all your filters:
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!

Holiday Rental House
12 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!

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Cove Point Beach Retreat. Fossil Hunting & More. Come Relax & Explore!!, vacation rental in Taylors Island
Cove Point Beach Retreat. Fossil Hunting & More. Come Relax & Explore!!, vacation rental in Taylors Island
Cove Point Beach Retreat. Fossil Hunting & More. Come Relax & Explore!!, vacation rental in Taylors Island

Cove Point Beach Retreat. Fossil Hunting & More. Come Relax & Explore!!

Holiday Rental House
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Breezes - quiet waterfront retreat, vacation rental in Taylors Island
Sunset Breezes - quiet waterfront retreat, vacation rental in Taylors Island
Sunset Breezes - quiet waterfront retreat, vacation rental in Taylors Island

Sunset Breezes - quiet waterfront retreat

Holiday Rental House
3 bedrooms
2 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

Holiday Rental House
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.

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
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
1 bedroom
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

Holiday Rental House
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!

Holiday Rental House
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!

Holiday Rental House
4 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. �

Holiday Rental House
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!

Holiday Rental House
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

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
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

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to, vacation rental in Taylors Island
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to, vacation rental in Taylors Island
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to, vacation rental in Taylors Island

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal, vacation rental in Taylors Island
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal, vacation rental in Taylors Island
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal, vacation rental in Taylors Island

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront retreat, beautiful views!, vacation rental in Taylors Island
Waterfront retreat, beautiful views!, vacation rental in Taylors Island
Waterfront retreat, beautiful views!, vacation rental in Taylors Island

Waterfront retreat, beautiful views!

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 22
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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

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou, vacation rental in Taylors Island
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou, vacation rental in Taylors Island
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou, vacation rental in Taylors Island

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

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

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

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub, vacation rental in Taylors Island
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub, vacation rental in Taylors Island
Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub, vacation rental in Taylors Island

Short drive to Downtown Cambridge | Private Dock | Guest House | Pool | Hot Tub

Holiday Rental House
8 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

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 28
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

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge, vacation rental in Taylors Island
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge, vacation rental in Taylors Island
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge, vacation rental in Taylors Island

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Eagles Nest.  Discover Tranquility, Privacy, Excellence, and so much more., vacation rental in Taylors Island
Eagles Nest.  Discover Tranquility, Privacy, Excellence, and so much more., vacation rental in Taylors Island
Eagles Nest.  Discover Tranquility, Privacy, Excellence, and so much more., vacation rental in Taylors Island

Eagles Nest. Discover Tranquility, Privacy, Excellence, and so much more.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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Farmhouse Charm Woolford Studio Apt. w/ Amazing Eastern Shore Sunrise, vacation rental in Taylors Island
Farmhouse Charm Woolford Studio Apt. w/ Amazing Eastern Shore Sunrise, vacation rental in Taylors Island
Farmhouse Charm Woolford Studio Apt. w/ Amazing Eastern Shore Sunrise, vacation rental in Taylors Island

Farmhouse Charm Woolford Studio Apt. w/ Amazing Eastern Shore Sunrise

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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"Endless Summer" Waterfront on the Chesapeake Bay!, vacation rental in Taylors Island
"Endless Summer" Waterfront on the Chesapeake Bay!, vacation rental in Taylors Island
"Endless Summer" Waterfront on the Chesapeake Bay!, vacation rental in Taylors Island

"Endless Summer" Waterfront on the Chesapeake Bay!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Fish, kayak, bike, and more at this private serene 24-acre waterfront estate., vacation rental in Taylors Island
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate., vacation rental in Taylors Island
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate., vacation rental in Taylors Island

Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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Cove Point Beach Cottage with Chesapeake Bay Views, vacation rental in Taylors Island
Cove Point Beach Cottage with Chesapeake Bay Views, vacation rental in Taylors Island
Cove Point Beach Cottage with Chesapeake Bay Views, vacation rental in Taylors Island

Cove Point Beach Cottage with Chesapeake Bay Views

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Taylors Island