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Talbot County Vacation Rentals

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97 rentals in Talbot County.
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Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, vacation rental in Talbot County
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, vacation rental in Talbot County
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, vacation rental in Talbot County

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, vacation rental in Talbot County
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, vacation rental in Talbot County
Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town, vacation rental in Talbot County

Large Luxury Waterfront Home with pool...... 2 1/2 miles from the center of town

Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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TRUE IN-TOWN SAINT MICHAELS 6 ACRE WATERFRONT w/POOL!!!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, vacation rental in Talbot County
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, vacation rental in Talbot County
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks, vacation rental in Talbot County

New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, vacation rental in Talbot County
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, vacation rental in Talbot County
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town, vacation rental in Talbot County

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, vacation rental in Talbot County
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, vacation rental in Talbot County
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, vacation rental in Talbot County

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Property, kayaks, private dock, near town, vacation rental in Talbot County
Waterfront Property, kayaks, private dock, near town, vacation rental in Talbot County
Waterfront Property, kayaks, private dock, near town, vacation rental in Talbot County

Waterfront Property, kayaks, private dock, near town

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), vacation rental in Talbot County
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), vacation rental in Talbot County
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS), vacation rental in Talbot County

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Rental Home
7 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in Talbot County
Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in Talbot County
Beautiful Tidewater home between Easton & ST Michaels!, vacation rental in Talbot County

Beautiful Tidewater home between Easton & ST Michaels!

Rental Home
4 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Fully remodel 2 bedroom country cottage., vacation rental in Talbot County
Fully remodel 2 bedroom country cottage., vacation rental in Talbot County
Fully remodel 2 bedroom country cottage., vacation rental in Talbot County

Fully remodel 2 bedroom country cottage.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in Talbot County
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in Talbot County
Waterfront Cottage, Private Hot Tub, Fire Pit - perfect Romantic Getaway, vacation rental in Talbot County

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!, vacation rental in Talbot County
Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!, vacation rental in Talbot County
Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!, vacation rental in Talbot County

Simplicity Cottage - Renovated Waterman's Home Circa 1920, Relax in the Hammock!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Comfy home on beautiful Leadenham Creek. Book now for summer!, vacation rental in Talbot County
Comfy home on beautiful Leadenham Creek. Book now for summer!, vacation rental in Talbot County
Comfy home on beautiful Leadenham Creek. Book now for summer!, vacation rental in Talbot County

Comfy home on beautiful Leadenham Creek. Book now for summer!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, vacation rental in Talbot County
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, vacation rental in Talbot County
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, vacation rental in Talbot County

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

Rental Home
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Cottage downtown on a quiet street, vacation rental in Talbot County
Cottage downtown on a quiet street, vacation rental in Talbot County
Cottage downtown on a quiet street, vacation rental in Talbot County

Cottage downtown on a quiet street

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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BREATHTAKING WATERFRONT ESTATE, vacation rental in Talbot County
BREATHTAKING WATERFRONT ESTATE, vacation rental in Talbot County
BREATHTAKING WATERFRONT ESTATE, vacation rental in Talbot County

BREATHTAKING WATERFRONT ESTATE

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Walk to Everything House, vacation rental in Talbot County
Walk to Everything House, vacation rental in Talbot County
Walk to Everything House, vacation rental in Talbot County

Walk to Everything House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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�Tuckaway Cove�Relaxing Private Getaway, St Michaels, MD, vacation rental in Talbot County
�Tuckaway Cove�Relaxing Private Getaway, St Michaels, MD, vacation rental in Talbot County
�Tuckaway Cove�Relaxing Private Getaway, St Michaels, MD, vacation rental in Talbot County

�Tuckaway Cove�Relaxing Private Getaway, St Michaels, MD

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*****Waterfront home w/ pool in St. Michaels, vacation rental in Talbot County
*****Waterfront home w/ pool in St. Michaels, vacation rental in Talbot County
*****Waterfront home w/ pool in St. Michaels, vacation rental in Talbot County

*****Waterfront home w/ pool in St. Michaels

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Looking to get away this September? Gorgeous waterfront property awaits., vacation rental in Talbot County
Looking to get away this September? Gorgeous waterfront property awaits., vacation rental in Talbot County
Looking to get away this September? Gorgeous waterfront property awaits., vacation rental in Talbot County

Looking to get away this September? Gorgeous waterfront property awaits.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Location Location! St Michaels-- In Town Cottage!, vacation rental in Talbot County
Location Location! St Michaels-- In Town Cottage!, vacation rental in Talbot County
Location Location! St Michaels-- In Town Cottage!, vacation rental in Talbot County

Location Location! St Michaels-- In Town Cottage!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Relax in Tilghman Island, vacation rental in Talbot County
Relax in Tilghman Island, vacation rental in Talbot County
Relax in Tilghman Island, vacation rental in Talbot County

Relax in Tilghman Island

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Oxford Waterfront Estate, vacation rental in Talbot County
Historic Oxford Waterfront Estate, vacation rental in Talbot County
Historic Oxford Waterfront Estate, vacation rental in Talbot County

Historic Oxford Waterfront Estate

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Premier Cottage in St. Michaels- In Town Location!, vacation rental in Talbot County
Premier Cottage in St. Michaels- In Town Location!, vacation rental in Talbot County
Premier Cottage in St. Michaels- In Town Location!, vacation rental in Talbot County

Premier Cottage in St. Michaels- In Town Location!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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New-Gorgeous Private Waterfront Home, Dock, Huge Deck&Heated Swim Spa, 2 MBR, vacation rental in Talbot County
New-Gorgeous Private Waterfront Home, Dock, Huge Deck&Heated Swim Spa, 2 MBR, vacation rental in Talbot County
New-Gorgeous Private Waterfront Home, Dock, Huge Deck&Heated Swim Spa, 2 MBR, vacation rental in Talbot County

New-Gorgeous Private Waterfront Home, Dock, Huge Deck&Heated Swim Spa, 2 MBR

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, vacation rental in Talbot County
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, vacation rental in Talbot County
BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!, vacation rental in Talbot County

BEAUTIFUL WATERFRONT HOME AVAILABLE NOW!!!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Waterview Cottage - St. Michaels Getaway, vacation rental in Talbot County
Perfect Waterview Cottage - St. Michaels Getaway, vacation rental in Talbot County
Perfect Waterview Cottage - St. Michaels Getaway, vacation rental in Talbot County

Perfect Waterview Cottage - St. Michaels Getaway

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Time to book your 2020 Sunset vacation!, vacation rental in Talbot County
Time to book your 2020 Sunset vacation!, vacation rental in Talbot County
Time to book your 2020 Sunset vacation!, vacation rental in Talbot County

Time to book your 2020 Sunset vacation!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, vacation rental in Talbot County
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, vacation rental in Talbot County
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, vacation rental in Talbot County

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Tilghman Island Cottage - Across from Marina and Knapps Narrows, vacation rental in Talbot County
Tilghman Island Cottage - Across from Marina and Knapps Narrows, vacation rental in Talbot County
Tilghman Island Cottage - Across from Marina and Knapps Narrows, vacation rental in Talbot County

Tilghman Island Cottage - Across from Marina and Knapps Narrows

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, vacation rental in Talbot County
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, vacation rental in Talbot County
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels, vacation rental in Talbot County

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

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Talbot County
St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Talbot County
St. Michaels Area Cottage - Walk to Water & Marina, vacation rental in Talbot County

St. Michaels Area Cottage - Walk to Water & Marina

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Talbot County
Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Talbot County
Charming 3 Bedroom 3 Bath Beach Front Property, vacation rental in Talbot County

Charming 3 Bedroom 3 Bath Beach Front Property

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, vacation rental in Talbot County
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, vacation rental in Talbot County
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!, vacation rental in Talbot County

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Eastern Shore Getaway Near St. Michaels, vacation rental in Talbot County
Eastern Shore Getaway Near St. Michaels, vacation rental in Talbot County
Eastern Shore Getaway Near St. Michaels, vacation rental in Talbot County

Eastern Shore Getaway Near St. Michaels

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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FANTASTIC WATERFRONT HOME WITH BEACH AWAITS!, vacation rental in Talbot County
FANTASTIC WATERFRONT HOME WITH BEACH AWAITS!, vacation rental in Talbot County
FANTASTIC WATERFRONT HOME WITH BEACH AWAITS!, vacation rental in Talbot County

FANTASTIC WATERFRONT HOME WITH BEACH AWAITS!

Rental Home
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Getaway on the Choptank River, vacation rental in Talbot County
Waterfront Getaway on the Choptank River, vacation rental in Talbot County
Waterfront Getaway on the Choptank River, vacation rental in Talbot County

Waterfront Getaway on the Choptank River

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!, vacation rental in Talbot County
Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!, vacation rental in Talbot County
Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!, vacation rental in Talbot County

Caulk's Cove - Waterfront Near St. Michaels, Bikes, Kayaks!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!, vacation rental in Talbot County
Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!, vacation rental in Talbot County
Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!, vacation rental in Talbot County

Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Osprey Point - Tranquil Waterfront Cottage w/ Pool & Kayaks - Pets Welcome!, vacation rental in Talbot County
Osprey Point - Tranquil Waterfront Cottage w/ Pool & Kayaks - Pets Welcome!, vacation rental in Talbot County
Osprey Point - Tranquil Waterfront Cottage w/ Pool & Kayaks - Pets Welcome!, vacation rental in Talbot County

Osprey Point - Tranquil Waterfront Cottage w/ Pool & Kayaks - Pets Welcome!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Talbot County
Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Talbot County
Holidays at the Cove  - plenty of space to gather while making memories, vacation rental in Talbot County

Holidays at the Cove - plenty of space to gather while making memories

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in Talbot County
Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in Talbot County
Large Historic Thomas Harrison House on Harbor in St. Michaels Town, vacation rental in Talbot County

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

Rental Home
7 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in Talbot County
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in Talbot County
Luxury Waterfront with pool and deep water dock, minutes from St Michaels., vacation rental in Talbot County

Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Main House at Grandview at Pleasure Point, vacation rental in Talbot County
Main House at Grandview at Pleasure Point, vacation rental in Talbot County
Main House at Grandview at Pleasure Point, vacation rental in Talbot County

Main House at Grandview at Pleasure Point

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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New Modern Waterfront Farmhouse Built 2018, vacation rental in Talbot County
New Modern Waterfront Farmhouse Built 2018, vacation rental in Talbot County
New Modern Waterfront Farmhouse Built 2018, vacation rental in Talbot County

New Modern Waterfront Farmhouse Built 2018

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home with Magnificent Views, vacation rental in Talbot County
Waterfront Home with Magnificent Views, vacation rental in Talbot County
Waterfront Home with Magnificent Views, vacation rental in Talbot County

Waterfront Home with Magnificent Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Crabber's Cove - Charming Waterfront Cottage Near St. Michaels, Kayaks & Bikes!, vacation rental in Talbot County
Crabber's Cove - Charming Waterfront Cottage Near St. Michaels, Kayaks & Bikes!, vacation rental in Talbot County
Crabber's Cove - Charming Waterfront Cottage Near St. Michaels, Kayaks & Bikes!, vacation rental in Talbot County

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Riverview Retreat - Charming Waterfront Cottage in St Michaels!, vacation rental in Talbot County
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, vacation rental in Talbot County
Riverview Retreat - Charming Waterfront Cottage in St Michaels!, vacation rental in Talbot County

Riverview Retreat - Charming Waterfront Cottage in St Michaels!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Large waterfront estate with breathtaking sunset views, vacation rental in Talbot County
Large waterfront estate with breathtaking sunset views, vacation rental in Talbot County
Large waterfront estate with breathtaking sunset views, vacation rental in Talbot County

Large waterfront estate with breathtaking sunset views

Rental Home
8 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Frequently Asked Questions about Talbot County