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Holiday Rentals in Talbot County

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Bedrooms

Bathrooms

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5 km
178 rentals in Talbot County.
Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Talbot County
Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Talbot County
Relaxing Waterfront Cottage Near St Michaels, Maryland, holiday rental in Talbot County

Relaxing Waterfront Cottage Near St Michaels, Maryland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Cottage 1a at Grandview Pleasure Point, holiday rental in Talbot County
Cottage 1a at Grandview Pleasure Point, holiday rental in Talbot County
Cottage 1a at Grandview Pleasure Point, holiday rental in Talbot County

Cottage 1a at Grandview Pleasure Point

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stay in the HEART of Saint Michaels!, holiday rental in Talbot County
Stay in the HEART of Saint Michaels!, holiday rental in Talbot County
Stay in the HEART of Saint Michaels!, holiday rental in Talbot County

Stay in the HEART of Saint Michaels!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, holiday rental in Talbot County
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, holiday rental in Talbot County
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, holiday rental in Talbot County

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Delightful Close to town, holiday rental in Talbot County
Delightful Close to town, holiday rental in Talbot County
Delightful Close to town, holiday rental in Talbot County

Delightful Close to town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Breathtaking Waterfront Estate, holiday rental in Talbot County
Breathtaking Waterfront Estate, holiday rental in Talbot County
Breathtaking Waterfront Estate, holiday rental in Talbot County

Breathtaking Waterfront Estate

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, holiday rental in Talbot County
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, holiday rental in Talbot County
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, holiday rental in Talbot County

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Great prices on a available days left!!! 
Beautiful Leadenham Creek. STR #22-30, holiday rental in Talbot County
Great prices on a available days left!!! 
Beautiful Leadenham Creek. STR #22-30, holiday rental in Talbot County
Great prices on a available days left!!! 
Beautiful Leadenham Creek. STR #22-30, holiday rental in Talbot County

Great prices on a available days left!!! Beautiful Leadenham Creek. STR #22-30

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton, holiday rental in Talbot County
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton, holiday rental in Talbot County
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton, holiday rental in Talbot County

Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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St. Michaels Waterfront Home, holiday rental in Talbot County
St. Michaels Waterfront Home, holiday rental in Talbot County
St. Michaels Waterfront Home, holiday rental in Talbot County

St. Michaels Waterfront Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk to Everything House, holiday rental in Talbot County
Walk to Everything House, holiday rental in Talbot County
Walk to Everything House, holiday rental in Talbot County

Walk to Everything House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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 Waterview Cottage In St. Michaels!, holiday rental in Talbot County
 Waterview Cottage In St. Michaels!, holiday rental in Talbot County
 Waterview Cottage In St. Michaels!, holiday rental in Talbot County

Waterview Cottage In St. Michaels!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cottage 1b at Grandview Pleasure Point, holiday rental in Talbot County
Cottage 1b at Grandview Pleasure Point, holiday rental in Talbot County
Cottage 1b at Grandview Pleasure Point, holiday rental in Talbot County

Cottage 1b at Grandview Pleasure Point

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Trend Setting Waterfront minutes to St. Michaels  -, holiday rental in Talbot County
Trend Setting Waterfront minutes to St. Michaels  -, holiday rental in Talbot County
Trend Setting Waterfront minutes to St. Michaels  -, holiday rental in Talbot County

Trend Setting Waterfront minutes to St. Michaels -

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cottage at Goose Neck Point, holiday rental in Talbot County
Cottage at Goose Neck Point, holiday rental in Talbot County
Cottage at Goose Neck Point, holiday rental in Talbot County

Cottage at Goose Neck Point

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, holiday rental in Talbot County
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, holiday rental in Talbot County
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, holiday rental in Talbot County

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Waterfront Home with Magnificent Views, holiday rental in Talbot County
Waterfront Home with Magnificent Views, holiday rental in Talbot County
Waterfront Home with Magnificent Views, holiday rental in Talbot County

Waterfront Home with Magnificent Views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Dollhouse in Central Historic St Michaels, holiday rental in Talbot County
Dollhouse in Central Historic St Michaels, holiday rental in Talbot County
Dollhouse in Central Historic St Michaels, holiday rental in Talbot County

Dollhouse in Central Historic St Michaels

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Luxurious studio in heart of historic St Michaels!, holiday rental in Talbot County
Luxurious studio in heart of historic St Michaels!, holiday rental in Talbot County
Luxurious studio in heart of historic St Michaels!, holiday rental in Talbot County

Luxurious studio in heart of historic St Michaels!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!, holiday rental in Talbot County
St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!, holiday rental in Talbot County
St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!, holiday rental in Talbot County

St. Michael's Premier In-Town Rental with pool and 2023 Designer updates!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Fabulous in town luxury studio, holiday rental in Talbot County
Fabulous in town luxury studio, holiday rental in Talbot County
Fabulous in town luxury studio, holiday rental in Talbot County

Fabulous in town luxury studio

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels, holiday rental in Talbot County
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels, holiday rental in Talbot County
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels, holiday rental in Talbot County

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, holiday rental in Talbot County
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, holiday rental in Talbot County
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, holiday rental in Talbot County

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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RANCH AT ROYAL OAK- Exclusive waterfront pool pier, holiday rental in Talbot County
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, holiday rental in Talbot County
RANCH AT ROYAL OAK- Exclusive waterfront pool pier, holiday rental in Talbot County

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Talbot County
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Talbot County
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, holiday rental in Talbot County

Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Historic Oxford Waterfront Estate, holiday rental in Talbot County
Historic Oxford Waterfront Estate, holiday rental in Talbot County
Historic Oxford Waterfront Estate, holiday rental in Talbot County

Historic Oxford Waterfront Estate

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxurious waterfront home - Cèilidh, holiday rental in Talbot County
Luxurious waterfront home - Cèilidh, holiday rental in Talbot County
Luxurious waterfront home - Cèilidh, holiday rental in Talbot County

Luxurious waterfront home - Cèilidh

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, holiday rental in Talbot County
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, holiday rental in Talbot County
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels, holiday rental in Talbot County

Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres, holiday rental in Talbot County
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres, holiday rental in Talbot County
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres, holiday rental in Talbot County

Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Eastern Shore Getaway Near St. Michaels, holiday rental in Talbot County
Eastern Shore Getaway Near St. Michaels, holiday rental in Talbot County
Eastern Shore Getaway Near St. Michaels, holiday rental in Talbot County

Eastern Shore Getaway Near St. Michaels

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Book 3 nights in July/August 4 night is free!, holiday rental in Talbot County
Book 3 nights in July/August 4 night is free!, holiday rental in Talbot County
Book 3 nights in July/August 4 night is free!, holiday rental in Talbot County

Book 3 nights in July/August 4 night is free!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Waterfront Property, kayaks, private dock, near town, holiday rental in Talbot County
Waterfront Property, kayaks, private dock, near town, holiday rental in Talbot County
Waterfront Property, kayaks, private dock, near town, holiday rental in Talbot County

Waterfront Property, kayaks, private dock, near town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Seventh Haven - An oasis of peace and relaxation!, holiday rental in Talbot County
Seventh Haven - An oasis of peace and relaxation!, holiday rental in Talbot County
Seventh Haven - An oasis of peace and relaxation!, holiday rental in Talbot County

Seventh Haven - An oasis of peace and relaxation!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Last minute change, so book July 8 now and save!, holiday rental in Talbot County
Last minute change, so book July 8 now and save!, holiday rental in Talbot County
Last minute change, so book July 8 now and save!, holiday rental in Talbot County

Last minute change, so book July 8 now and save!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, holiday rental in Talbot County
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, holiday rental in Talbot County
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, holiday rental in Talbot County

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Harbor View Suite, holiday rental in Talbot County
Harbor View Suite, holiday rental in Talbot County
Harbor View Suite, holiday rental in Talbot County

Harbor View Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, holiday rental in Talbot County
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, holiday rental in Talbot County
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, holiday rental in Talbot County

Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Memory Lane - Charming Cottage in the Heart of Oxford, Pet Friendly!, holiday rental in Talbot County
Memory Lane - Charming Cottage in the Heart of Oxford, Pet Friendly!, holiday rental in Talbot County
Memory Lane - Charming Cottage in the Heart of Oxford, Pet Friendly!, holiday rental in Talbot County

Memory Lane - Charming Cottage in the Heart of Oxford, Pet Friendly!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, holiday rental in Talbot County
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, holiday rental in Talbot County
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!, holiday rental in Talbot County

SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Thorneton Point Estate, holiday rental in Talbot County
Thorneton Point Estate, holiday rental in Talbot County
Thorneton Point Estate, holiday rental in Talbot County

Thorneton Point Estate

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Perfect Waterview Cottage - St. Michaels Getaway, holiday rental in Talbot County
Perfect Waterview Cottage - St. Michaels Getaway, holiday rental in Talbot County
Perfect Waterview Cottage - St. Michaels Getaway, holiday rental in Talbot County

Perfect Waterview Cottage - St. Michaels Getaway

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in Talbot County
Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in Talbot County
Beautiful Waterfront Home w/ Pool In St. Michaels, holiday rental in Talbot County

Beautiful Waterfront Home w/ Pool In St. Michaels

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront  - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM 
LANDING, holiday rental in Talbot County
Waterfront  - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM 
LANDING, holiday rental in Talbot County
Waterfront  - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM 
LANDING, holiday rental in Talbot County

Waterfront - NEW BOOK AUG/SEPT AND RECEIVE 100 CERT FOR SEAFOOD FROM LANDING

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Riverview Retreat - Charming Waterfront Cottage in St Michaels!, holiday rental in Talbot County
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, holiday rental in Talbot County
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, holiday rental in Talbot County

Riverview Retreat - Charming Waterfront Cottage in St Michaels!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quaint Tilghman Island home, holiday rental in Talbot County
Quaint Tilghman Island home, holiday rental in Talbot County
Quaint Tilghman Island home, holiday rental in Talbot County

Quaint Tilghman Island home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated Guest House located in Oxford MD, holiday rental in Talbot County
Newly Renovated Guest House located in Oxford MD, holiday rental in Talbot County
Newly Renovated Guest House located in Oxford MD, holiday rental in Talbot County

Newly Renovated Guest House located in Oxford MD

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, holiday rental in Talbot County
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, holiday rental in Talbot County
Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!, holiday rental in Talbot County

Crabber's Cove - Charming Waterfront Near St. Michaels, Kayaks & Bikes!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, holiday rental in Talbot County
EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, holiday rental in Talbot County
EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places, holiday rental in Talbot County

EASTON Beautiful APT. 2bed2bathKitchinDining/living room-walk to all places

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Modern Studio in heart of town., holiday rental in Talbot County
Modern Studio in heart of town., holiday rental in Talbot County
Modern Studio in heart of town., holiday rental in Talbot County

Modern Studio in heart of town.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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5 bedroom Bed and Breakfast on the Choptank River, holiday rental in Talbot County
5 bedroom Bed and Breakfast on the Choptank River, holiday rental in Talbot County
5 bedroom Bed and Breakfast on the Choptank River, holiday rental in Talbot County

5 bedroom Bed and Breakfast on the Choptank River

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-50 of 178
Frequently Asked Questions about Talbot County