Talbot Area Vacation Rentals - Talbot Area, Maryland Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

ENDLESS SUNSETS ON THE EASTERN BAY

ENDLESS SUNSETS ON THE EASTERN BAY

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Claiborne Maryland Private vacation home From $676 per night (USD)

Historic Oxford Waterfront Estate

Historic Oxford Waterfront Estate

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Oxford Maryland Private vacation home From $1180 per night (USD)

St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27

St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27

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St. Michaels Maryland Cottage From $516 per night (USD)

20% Off 5 Night Min. Waterfront, Hot Tub, Pool,Minutes to St.Michaels.

20% Off 5 Night Min. Waterfront, Hot Tub, Pool,Minutes to St.Michaels.

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Royal Oak Maryland Private vacation home From $857 per night (USD)

Charming cottage along water with private pier, near St. Michaels Winery

Charming cottage along water with private pier, near St. Michaels Winery

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Bozman Maryland Cottage From $322 per night (USD)

Cottage at Goose Neck Point

Cottage at Goose Neck Point

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Royal Oak Maryland Cottage From $549 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury

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Royal Oak Maryland Private vacation home From $2729 per night (USD)

The B&B of Anchorage - Skipjack

The B&B of Anchorage - Skipjack

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Trappe Maryland Bed & breakfast From $352 per night (USD)

Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels

Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels

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Tilghman Island Maryland Private vacation home From $1005 per night (USD)

ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS PET FRIENDLY

ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS PET FRIENDLY

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Sherwood Maryland Private vacation home From $1638 per night (USD)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

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Saint Michaels Maryland Private vacation home From $398 per night (USD)

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

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

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St. Michaels Maryland Private vacation home From $741 per night (USD)

Stay in the HEART of Saint Michaels!

Stay in the HEART of Saint Michaels!

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St Michaels Maryland Private vacation home From $382 per night (USD)

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

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

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St Michaels Maryland Cottage From $374 per night (USD)

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

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St Michaels Maryland Private vacation home From $821 per night (USD)

Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay

Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay

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Tilghman Maryland Private vacation home From $601 per night (USD)

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

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

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Saint Michaels Maryland Cottage From $413 per night (USD)

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

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easton Maryland Private vacation home From $1203 per night (USD)

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

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

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Easton Maryland Private vacation home From $843 per night (USD)

Thorneton Point Estate

Thorneton Point Estate

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Easton Maryland Private vacation home From $998 per night (USD)

Breathtaking Waterfront Estate

Breathtaking Waterfront Estate

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Neavitt Maryland Villa From $967 per night (USD)

House on the Chesapeake Bay

House on the Chesapeake Bay

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Tilghman Island Maryland Private vacation home From $678 per night (USD)

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

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Sherwood Maryland Private vacation home From $1583 per night (USD)

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

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Oxford Maryland Private vacation home From $993 per night (USD)

We still have availability for August to October 2026 STR #22-30

We still have availability for August to October 2026 STR #22-30

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Bozman Maryland Private vacation home From $488 per night (USD)

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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St. Michaels Maryland Private vacation home From $971 per night (USD)

Relax or Play on the Choptank River!

Relax or Play on the Choptank River!

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Trappe Maryland Hotel resort From $374 per night (USD)

Luxurious waterfront home - Cèilidh

Luxurious waterfront home - Cèilidh

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Oxford Maryland Private vacation home From $1031 per night (USD)

Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C

Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C

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Saint Michaels Maryland Private vacation home From $1539 per night (USD)

The Anchorage B&B - The Bounty

The Anchorage B&B - The Bounty

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Trappe Maryland Private vacation home From $301 per night (USD)

Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

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Easton Maryland Private vacation home From $1363 per night (USD)

Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!

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Tilghman Maryland Private vacation home From $813 per night (USD)

🌊 Book Now for 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

🌊 Book Now for 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

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Royal Oak Maryland Private vacation home From $568 per night (USD)

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

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St. Michaels Maryland Private vacation home From $924 per night (USD)

Tilghman | Pool | Private Dock | Pet Friendly

Tilghman | Pool | Private Dock | Pet Friendly

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Tilghman Maryland Private vacation home From $947 per night (USD)

Downtown Oxford | Charming | Pet Friendly

Downtown Oxford | Charming | Pet Friendly

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Oxford Maryland Private vacation home From $777 per night (USD)

Minutes from Downtown St. Michaels | Private Dock | Kayaks

Minutes from Downtown St. Michaels | Private Dock | Kayaks

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Saint Michaels Maryland Private vacation home From $816 per night (USD)

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

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Wittman Maryland Cottage From $277 per night (USD)

LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, DOCK, GOURMET KITCHEN

LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, DOCK, GOURMET KITCHEN

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Saint Michaels Maryland Agritourism From $1593 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |

Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |

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Saint Michaels Maryland Private vacation home From $1023 per night (USD)

BOOK NOW FOR SPRING & SUMMER DATES.

BOOK NOW FOR SPRING & SUMMER DATES.

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Tilghman Island Maryland Private vacation home From $533 per night (USD)

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

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Easton Maryland Private vacation home Click For Pricing

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

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St Michaels Maryland Private vacation home From $329 per night (USD)

Downtown St. Michaels | Bikes | Kayaks | Private Pier

Downtown St. Michaels | Bikes | Kayaks | Private Pier

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Saint Michaels Maryland Private vacation home From $1024 per night (USD)

Baydream Believer

Baydream Believer

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Talbot County Maryland Private vacation home From $1164 per night (USD)

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

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

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Wittman Maryland Private vacation home From $1277 per night (USD)

St. Michaels Waterfront Home

St. Michaels Waterfront Home

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New comb Maryland Private vacation home From $621 per night (USD)

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

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

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Saint Michaels Maryland Cottage From $374 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat

Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat

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Easton Maryland Private vacation home From $1387 per night (USD)

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

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

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St Michaels Maryland Cottage From $329 per night (USD)

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

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Tilghman Island Maryland Private vacation home From $527 per night (USD)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

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Easton Maryland Private vacation home From $1092 per night (USD)

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

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

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Easton Maryland Guest house From $493 per night (USD)

Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock

Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock

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Neavitt Maryland Private vacation home From $856 per night (USD)

Walk to Everything House

Walk to Everything House

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Saint Michaels Maryland Private vacation home From $361 per night (USD)

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

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St. Michaels Maryland Cottage From $630 per night (USD)

Modern room with walk in shower and kitchenette

Modern room with walk in shower and kitchenette

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Trappe Maryland Bed & breakfast From $349 per night (USD)

Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Eastern Shore MD

Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Eastern Shore MD

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Oxford Maryland Apart-hotel From $280 per night (USD)

Sandaway Suites & Beach Boutique Hotel, Private Beach, Walk to Dining & Shops!

Sandaway Suites & Beach Boutique Hotel, Private Beach, Walk to Dining & Shops!

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Oxford Maryland Hotel From $333 per night (USD)

Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Oxford, Maryland

Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Oxford, Maryland

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Oxford Maryland Apart-hotel From $333 per night (USD)

Waterfront Property, kayaks, private dock, near town

Waterfront Property, kayaks, private dock, near town

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St. Michaels Maryland Private vacation home From $900 per night (USD)

TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool

TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool

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St Michaels Maryland Private vacation home From $1246 per night (USD)

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

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Royal Oak Maryland Private vacation home From $1019 per night (USD)

Stunning views at WATERFRONT St Michaels area historic home, dog friendly

Stunning views at WATERFRONT St Michaels area historic home, dog friendly

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Neavitt Maryland Private vacation home From $392 per night (USD)

Perfect Waterview Cottage - St. Michaels Getaway

Perfect Waterview Cottage - St. Michaels Getaway

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Wittman Maryland Cottage From $298 per night (USD)

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

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

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Sherwood Maryland Private vacation home From $357 per night (USD)

Grandview- Main House

Grandview- Main House

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Bozman Maryland Private vacation home From $985 per night (USD)

Secluded Waterfront Property on 3 acres with swimming pool and dock.

Secluded Waterfront Property on 3 acres with swimming pool and dock.

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Bozman Maryland Private vacation home From $1089 per night (USD)

Tilghman | Fenced Yard | Pet Friendly | Charming

Tilghman | Fenced Yard | Pet Friendly | Charming

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Tilghman Maryland Private vacation home From $748 per night (USD)

Harbor View Suite Talbot County License Number STRN-25-58

Harbor View Suite Talbot County License Number STRN-25-58

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Saint Michaels Maryland Apartment From $313 per night (USD)

Eastern Shore Oasis!

Eastern Shore Oasis!

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Easton Maryland Private vacation home From $1005 per night (USD)

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

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St. Michaels Maryland Private vacation home From $1099 per night (USD)

Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova

Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova

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Bozman Maryland Private vacation home From $1430 per night (USD)

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

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Easton Maryland Private vacation home From $438 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

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Easton Maryland Private vacation home From $2045 per night (USD)

Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels

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Neavitt Maryland Cottage From $484 per night (USD)

Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court

Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court

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Saint Michaels Maryland Private vacation home From $937 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

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Easton Maryland Private vacation home From $1388 per night (USD)

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

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Sherwood Maryland Private vacation home From $1332 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

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Easton Maryland Private vacation home From $1003 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours

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Easton Maryland Private vacation home From $2591 per night (USD)

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining

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Sherwood Maryland Private vacation home From $610 per night (USD)

Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops

Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops

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Saint Michaels Maryland Apartment From $372 per night (USD)

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

Minutes from Downtown Easton and St. Michaels | Pool | Private Dock

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Easton Maryland Private vacation home From $1051 per night (USD)

St. Michaels Escape | Pool, Hot Tub & Fire Pit

St. Michaels Escape | Pool, Hot Tub & Fire Pit

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Saint Michaels Maryland Private vacation home From $1297 per night (USD)

Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur

Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur

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Saint Michaels Maryland Private vacation home From $1567 per night (USD)

Downtown Retreat with Bikes, Fire Pit & Kayaks

Downtown Retreat with Bikes, Fire Pit & Kayaks

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Saint Michaels Maryland Private vacation home From $582 per night (USD)

NEWLY Renovated Waterfront Farmhouse in Private Setting!!!

NEWLY Renovated Waterfront Farmhouse in Private Setting!!!

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Bozman Maryland Private vacation home From $1049 per night (USD)

$\Point of View\ Waterfront cottage with panoramic views on Tilghman Island$

\"Point of View\" Waterfront cottage with panoramic views on Tilghman Island

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Tilghman Island Maryland Cottage From $331 per night (USD)

Pet-Friendly Tilghman Island Coastal Retreat

Pet-Friendly Tilghman Island Coastal Retreat

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Tilghman Island Maryland Private vacation home From $424 per night (USD)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

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Tilghman Island Maryland Cottage From $529 per night (USD)

Ferry Bridge House

Ferry Bridge House

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Talbot County Maryland Private vacation home From $858 per night (USD)

Enjoy the beautiful reflections of sunsets and the golden leaves on the water!

Enjoy the beautiful reflections of sunsets and the golden leaves on the water!

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Bozman Maryland Private vacation home From $998 per night (USD)

Adorable, well-appointed cottage on 2 ac. overlooking beautiful Long Haul Creek

Adorable, well-appointed cottage on 2 ac. overlooking beautiful Long Haul Creek

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St. Michaels Maryland Cottage From $720 per night (USD)

Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled

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Oxford Maryland Private vacation home From $763 per night (USD)

Waterfront home with private dock near St. Michaels & Easton

Waterfront home with private dock near St. Michaels & Easton

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Easton Maryland Private vacation home From $1048 per night (USD)

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

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St. Michaels Maryland Private vacation home From $1688 per night (USD)

Minutes from Downtown St. Michaels | Pool | Hot Tub

Minutes from Downtown St. Michaels | Pool | Hot Tub

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Bozman Maryland Private vacation home From $727 per night (USD)

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

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Trappe Maryland Private vacation home From $427 per night (USD)

Heated pool, sandy beach, pier, and playground set punch point apart!

Heated pool, sandy beach, pier, and playground set punch point apart!

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Sherwood Maryland Private vacation home From $1302 per night (USD)

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