Talbot Area Rentals
From $1185 per night (USD)VRBO
Minutes from Downtown Easton and St. Michaels | Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your dream retreat, nestled in a serene cove that feels like a page from a fairytale. This enchanting waterfr ...
From $1185 per night (USD)VRBO
From $366 per night (USD)Expedia
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience Easton like a local in this marvelous 4-bedroom house. With 2 king beds and 2 queen beds, this charming prope ...
From $366 per night (USD)Expedia
From $553 per night (USD)VRBO
Minutes from Downtown St. Michaels | Private Boat Ramp | Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Love at First Sight Welcome to “Heron’s Roost,” an exceptional 3-bedroom, 2.5-bathroom haven nestled on 10 picturesque ...
From $553 per night (USD)VRBO
From $258 per night (USD)Expedia
Tilghman Island Retreat By Knapps Narrows!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Furnished Sunroom | Family Friendly | Half-Mi to Marina Make your way to this lovely Tilghman Island vacation rental, i ...
From $258 per night (USD)Expedia
From $1185 per night (USD)VRBO
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels POOL OPEN May to OCTOBER Relax with t ...
From $1185 per night (USD)VRBO
From $505 per night (USD)Expedia
Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to Coco’s Nest, your intimate escape in the charming historic district of Saint Michaels, Maryland. Per ...
From $505 per night (USD)Expedia
From $454 per night (USD)VRBO
Downtown Oxford | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ahoy there, mateys! Prepare to be captivated by this newly renovated 3-bedroom, 2-bathroom vacation rental in Oxford, ...
From $454 per night (USD)VRBO
From $395 per night (USD)VRBO
Brand-New Pool! Waterfront Bozman Village Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5 ...
From $395 per night (USD)VRBO
From $402 per night (USD)VRBO
Walk to Waterfront • Cozy Oxford Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Discover the charm of Maryland’s Eastern Shore at our cozy cottage nestled in the heart of Oxford. Just steps f ...
From $402 per night (USD)VRBO
From $1014 per night (USD)Expedia
Waterfront Paradise | Pool, Views & Serenity
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gather your favorite people and escape to a spacious waterfront haven in Royal Oak. From coffee at sunrise on ...
From $1014 per night (USD)Expedia
From $2152 per night (USD)VRBO
Waterfront Retreat wth Pool | Perfect for Late Summer & Fall Getaways
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: End your summer in style and welcome fall on Maryland’s Eastern Shore. At Eventide Farm, the seasons unfold bea ...
From $2152 per night (USD)VRBO
From $339 per night (USD)VRBO
The Snuggery Inn & Suites Sea Grass Room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This stylish place is within steps of all the shopping, dining, nightlife and museums. The Snuggery Inn & Suites offers ...
From $339 per night (USD)VRBO
From $440 per night (USD)VRBO
The Snuggery Inn & Suites Captain's Quarters
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This stylish place is within steps of all the shopping, dining, nightlife and museums. The Snuggery Inn & Suites offers ...
From $440 per night (USD)VRBO
From $274 per night (USD)Expedia
Charming Victorian Farmhouse on Historic Main St
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Easy US-50 Access | 2 Mi to Choptank River Your Eastern Shore adventure begins at this inviting Victorian farmhouse on ...
From $274 per night (USD)Expedia
From $377 per night (USD)VRBO
Charming Waterfront Cottage Retreat near St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the ultimate getaway at this stunning waterfront cottage on Maryland’s picturesque Eastern Shore, nestled minut ...
From $377 per night (USD)VRBO
From $364 per night (USD)VRBO
3Br/1Ba Pondview Langsdale House - A Historic Stay with Heart
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Pondview Langsdale House – A Historic Stay with Heart Step into a piece of Easton’s rich history at The Pondview Lan ...
From $364 per night (USD)VRBO
From $860 per night (USD)VRBO
Stunning Waterfront Escape with New Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Whether you're looking to relax poolside or explore the surrounding area, this waterfront home has everything y ...
From $860 per night (USD)VRBO
From $520 per night (USD)VRBO
Log Cabin, Woodland Retreat, Family & Pet-Friendly-St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Wales Family Cabin offers singles, couples, families, artists, writers, forest lovers and others a reprieve from the bus ...
From $520 per night (USD)VRBO
From $294 per night (USD)VRBO
Cottage #4 Chesapeake Blue down the drive way.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $294 per night (USD)VRBO
From $294 per night (USD)VRBO
#3 Mallard Cottage (located 3rd down drive)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $294 per night (USD)VRBO
From $224 per night (USD)VRBO
Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Pot Pie Cottage — your charming, well-priced escape just minutes from the historic town of St. Micha ...
From $224 per night (USD)VRBO
From $366 per night (USD)VRBO
Duck Cove Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR License - STRN-24-52 Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)VRBO
From $286 per night (USD)VRBO
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Stay steps from Saint Michaels’ best shops, dining, and waterfront views! This stylish studio blends historic c ...
From $286 per night (USD)VRBO
From $609 per night (USD)VRBO
St. Michaels Escape | Pool, Hot Tub & Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. ...
From $609 per night (USD)VRBO
From $163 per night (USD)VRBO
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The village of Sherwood is located on Harris Creek. The cottage, at 21902 Sherwood Landing Rd., is a perfect place to r ...
From $163 per night (USD)VRBO
From $624 per night (USD)Expedia
Grace Cottage, Saint Michaels Walk to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About this space Welcome to Grace Street Cottage in the heart of Saint Michaels. Walk to shops, restaurants and experien ...
From $624 per night (USD)Expedia
From $734 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Eastern Shore Vacation Rentals presents Crew's Quarters. Step into this idyllic, uniquely Eastern Shore Nanticoke mid- c ...
From $734 per night (USD)VRBO
From $1003 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Toto, There’s No Place Like This Vacation Home! The impressive 5BR, 3.5BA vacation estate with a free-flowing floor pla ...
From $1003 per night (USD)Expedia
From $836 per night (USD)VRBO
Eastern Shore Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Miles Away is a beautifully renovated 4 bedroom waterfront rancher with luxurious pool, wrap around deck and screened-in ...
From $836 per night (USD)VRBO
From $1355 per night (USD)VRBO
ST MICHAELS-Private Waterfront, Huge Deck& 19’Swim spa-pool, Kayaks, 2 MBRooms
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
YOUR CHESAPEAKE DREAM GETAWAY-SPECIAL NIGHTLY RATE OF $950 FOR BOOKINGS MAY 26-30,JULY 16-19 and JULY 27-8/2 Fantastic ...
From $1355 per night (USD)VRBO
From $845 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License STN-22-27 This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interio ...
From $845 per night (USD)VRBO
From $1073 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides ...
From $1073 per night (USD)Expedia
From $324 per night (USD)VRBO
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for an Eastern Shore waterfront retreat that's perfect for a romantic long weekend, a family vacation with the k ...
From $324 per night (USD)VRBO
From $571 per night (USD)VRBO
Grandview - Main House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
GRANDVIEW, which was once known as Grandview at Pleasure Point, is a private estate located on 5¼ acres of Maryland’s f ...
From $571 per night (USD)VRBO
From $183 per night (USD)VRBO
Cozy & Spacious, The Calway Inn
- Bedrooms:
- 1
- Bathrooms:
- 11
- Sleeps:
- 6
Summary: Take it easy at this unique and tranquil getaway. Situated right in the heart of this Talbot town, the Calway I ...
From $183 per night (USD)VRBO
From $867 per night (USD)Expedia
Downtown Oxford | Charming | Outdoor Dining
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This charming 4-bedroom, 3.5-bathroom cottage in the historic town of Oxford was designed with your vacation in mind. Th ...
From $867 per night (USD)Expedia
From $455 per night (USD)VRBO
Tilghman | Fenced Yard | Pet Friendly | Charming
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License #STN-22-20 This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-f ...
From $455 per night (USD)VRBO
From $528 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A Waterfront Oasis of Peace and Relaxation! This 3-bedroom, 2-bathroom offers an open floor plan character-filled inter ...
From $528 per night (USD)Expedia
From $668 per night (USD)VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy “the good old days” in style! This exceptional 4-bedroom, 3.5-bathroom home offers a character-filled interior an ...
From $668 per night (USD)VRBO
From $661 per night (USD)Expedia
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Shorely, this is a true outdoor paradise! Originally a waterman's cottage, Neavitt Cottage has been tastefully updated ...
From $661 per night (USD)Expedia
From $296 per night (USD)VRBO
Cottage downtown on a quiet street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In search of a cottage in downtown St. Michaels for a nice weekend? Located on a quiet street, yet steps away from shopp ...
From $296 per night (USD)VRBO
From $1095 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Hot Tub, Pool and Cabana House … Oh My! Built in 1930, this 5-bedroom, 3.5-bathroom waterfront getaway sits on 2.2 acre ...
From $1095 per night (USD)Expedia
From $398 per night (USD)VRBO
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This luxury home is nestled on a spacious lot, offering peaceful water views overlooking a beautiful pond. The 3-bedroom ...
From $398 per night (USD)VRBO
From $2113 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
One Of A Kind! Tranquil and timeless, Fairview is among the great historic estates of Talbot County. Offering a total o ...
From $2113 per night (USD)Expedia
From $1014 per night (USD)VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
O Say, Can You See Your Next Vacation? Don’t miss this truly exceptional 1950's ranch style 3BR, 2.5BA waterfront on th ...
From $1014 per night (USD)VRBO
From $1148 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License STN-23-31 Welcome to Gratitude Farm, a newly renovated 1890s farmhouse offering the ultimate ...
From $1148 per night (USD)Expedia
From $802 per night (USD)VRBO
NEWLY Renovated Waterfront Farmhouse in Private Setting!!!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STN-23-12 This charming 16+ acre waterfront farmhouse circa 1769 just underwent a massive renovation and interior redesi ...
From $802 per night (USD)VRBO
Click For PricingExpedia
Minutes from St. Michaels | Newly Renovated | Pool | Private Dock | Kayaks | Bik
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Your Unforgettable Waterfront Retreat! Escape to the unparalleled luxury of Eventide Farm, a waterfront retreat in St. ...
Click For PricingExpedia
From $1451 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout with your comfort in mi ...
From $1451 per night (USD)VRBO
Click For PricingExpedia
Seasonal Rental: Artisan designed 3 bedroom home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax St Michaels' style in this seasonal rental. This area of St Michaels requires a 4 month minimum stay ...
Click For PricingExpedia
From $521 per night (USD)VRBO
Cottage at Goose Neck Point
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming newly renovated cottage at the end of a private drive. Direct access to the Tred Avon River. Spectacular view ...
From $521 per night (USD)VRBO
From $1377 per night (USD)Expedia
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Licensed by Talbot Co MD STRN-23-11. Mimimum 7 night reservations only - Sat to Sat. Our property is ideally suited for ...
From $1377 per night (USD)Expedia
From $753 per night (USD)VRBO
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Escape to our 4-bedroom vacation home in Easton, just a 5-7 minute drive from the renowned St. Michaels. Immerse yoursel ...
From $753 per night (USD)VRBO
From $1179 per night (USD)Expedia
Thorneton Point Estate
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: **HEATABLE SPA** Nestled on the tip of an idyllic private 5 acre peninsula, minutes from historic St. Michaels, ...
From $1179 per night (USD)Expedia
From $432 per night (USD)VRBO
Historic Renovated Jackrabbit Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to th ...
From $432 per night (USD)VRBO
From $1024 per night (USD)Expedia
Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was d ...
From $1024 per night (USD)Expedia
From $1708 per night (USD)VRBO
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
Looking to getaway, relax and recharge? This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a sp ...
From $1708 per night (USD)VRBO
From $585 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An oasis of peace and relaxation! This 3-bedroom, 2.5-bathroom shingle style cottage offers a character-filled interior ...
From $585 per night (USD)Expedia
From $454 per night (USD)VRBO
3-bedroom historic vacation home newly renovated in the middle of Oxford MD.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated charming house in the middle of town. 1 block from the Chesapeake Bay, across the street from park/ play ...
From $454 per night (USD)VRBO
From $443 per night (USD)Expedia
Cozy 2BR Home near Idlewild Park\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
"Welcome to your cozy retreat in the heart of Easton, Maryland, a small, charming town nestled on Maryland's Eastern Sho ...
From $443 per night (USD)Expedia
From $668 per night (USD)VRBO
Arcadia Shores on the Cove.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Your home away from home in Easton with 4 bedrooms and 4 full baths. This sprawling rancher offers a tranquil and soothi ...
From $668 per night (USD)VRBO
From $284 per night (USD)VRBO
B&B - The Lawson
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This delightful bed & breakfast is the perfect home base for your visit. The property includes a small beach, Adirondack ...
From $284 per night (USD)VRBO
From $1419 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Outdoor Kitchen | Private Dock | Hot
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Discover Your Peaceful Escape! Welcome to your dream vacation estate, an impressive 5-bedroom, 5-full bathroom, 1-half ...
From $1419 per night (USD)VRBO
From $3687 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Pool House | Lu
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 12
Vacation like a rockstar at this 21+ acre luxury waterfront estate located on a protected cove off the Tred Avon River. ...
From $3687 per night (USD)Expedia
From $722 per night (USD)VRBO
Enjoy the beautiful reflections of sunsets and the golden leaves on the water!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-23-30 Just minutes from St Michaels this contemporary home is the perfect waterfront retreat. This home gives i ...
From $722 per night (USD)VRBO
From $496 per night (USD)Expedia
Downtown Oxford | Outdoor Dining | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This bright and airy 3BR, 2BA cape cod vacation home in Oxford is designed with your comfort in mind. The free-flowing f ...
From $496 per night (USD)Expedia
Click For PricingVRBO
Vacation Rental in Historic St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right ab ...
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From $999 per night (USD)Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A Perfect Single-Story Waterfront Retreat! Situated on a quiet 2+acre waterfront lot, this home is perfect for active f ...
From $999 per night (USD)Expedia
From $334 per night (USD)VRBO
\"Point of View\" Waterfront cottage with panoramic views on Tilghman Island
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Tilghman Island “Point of View” is a waterfront property located on Tilghman Island, with a 270-degree water view ov ...
From $334 per night (USD)VRBO
From $422 per night (USD)Expedia
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-58 Simplicity Cottage is a circa 1920 Waterman's Cottage. Wide water views and bay breezes! This fantastic 1920' ...
From $422 per night (USD)Expedia
From $861 per night (USD)VRBO
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This m ...
From $861 per night (USD)VRBO
Click For PricingExpedia
Spacious Family Getaway – Summer Ready!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Pack your bags and gather the crew—this bright and welcoming 4-bedroom, 4.5-bath home is everything a summer ge ...
Click For PricingExpedia
From $192 per night (USD)VRBO
Charming 1-bedroom cottage on the water, minutes from St Michaels MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
King Size Comfort. The ambience of each cottage is one of relaxed comfort. Fashionable cottage décor is enhanced with co ...
From $192 per night (USD)VRBO
From $247 per night (USD)VRBO
Waterfront cottage, 1 bd 1 bath, Perfect for your next getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The perfect couples’ getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhan ...
From $247 per night (USD)VRBO
From $283 per night (USD)VRBO
Charming 2-bedroom cottage, waterfront, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect, small family, getaway. The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is ...
From $283 per night (USD)VRBO
From $428 per night (USD)Expedia
Downtown Oxford | Outdoor Dining | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Old School Charm Meets New School Living! This charming 3BR, 2BA duplex vacation home within walking distance from Down ...
From $428 per night (USD)Expedia
From $294 per night (USD)VRBO
#2 Egret Cottage Harris Cove
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax with the whole family at this peaceful place to stay. Great Sunset and Sunrises, located on Harris Creek, each cot ...
From $294 per night (USD)VRBO
From $391 per night (USD)Expedia
Minutes from Downtown St. Michaels | Character Filled
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
TGIF … Escape to happiness, laughter, and unforgettable moments at The Weekender! This bright and airy 2-bedroom, 2.5- ...
From $391 per night (USD)Expedia
From $594 per night (USD)VRBO
Ferry Bridge House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Ferry Bridge House is a hidden gem that feels a world away from everyday life. This property is secluded but just a shor ...
From $594 per night (USD)VRBO
From $1540 per night (USD)Expedia
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County Rental License STRN-23-19 Stunning 22 acre property in prime location on the Tred Avon situated between ...
From $1540 per night (USD)Expedia
From $239 per night (USD)VRBO
Charming Summer Cottage – Relax and Unwind Here!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Summary: Tucked away at the peaceful tip of Tilghman Island, Skipjack Cottage sits in a neighborhood where life slows do ...
From $239 per night (USD)VRBO
From $267 per night (USD)Expedia
15% Off Promo! Tilghman Cottage by Views & Eats
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This isn’t just a place to stay. It’s a place to pause. To breathe. To remember what it feels like to just be. ...
From $267 per night (USD)Expedia
From $840 per night (USD)VRBO
Charming Waterfront Stay close to St. Michaels
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Miles View Villa, your private waterfront retreat near St. Michaels. This spacious 4-bedroom home of ...
From $840 per night (USD)VRBO
From $530 per night (USD)VRBO
Very cosy and nicely appointed Waterfront Cottage with gorgeous views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
License # STRN-24-69...A long, driveway leads to this updated and charming 1930's St. Michaels Cottage situated on two a ...
From $530 per night (USD)VRBO
From $1185 per night (USD)VRBO
LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Come slip away and enjoy Perry Point—a custom built nautical farmhouse that provides the best combination of luxury acco ...
From $1185 per night (USD)VRBO
From $441 per night (USD)Expedia
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your private escape on Tilghman Island — a waterfront home with panoramic water views, a dock for b ...
From $441 per night (USD)Expedia
From $300 per night (USD)VRBO
Modern Flat in the Heart of St. Michaels – Walk Everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Welcome to Flat 207, your private retreat in the heart of beautiful St. Michaels. Located just steps from the h ...
From $300 per night (USD)VRBO
From $552 per night (USD)Expedia
Waterfront Home on Chesapeake Bay with Dock, Bikes & Sunset Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to the quiet charm of Tilghman Island at this bright, open-concept waterfront home. Located directly on ...
From $552 per night (USD)Expedia
From $619 per night (USD)VRBO
AUGUST Bookings, 15% Off. Near St.Michaels/Easton Waterfront, Dock,Hot Tub.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Another Luxury VIP Vacation Rental Property on the eastern shore. License # STRN-22-25 Stay at this comfortable propert ...
From $619 per night (USD)VRBO
From $975 per night (USD)Expedia
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County MD License #STN-24-6 Water front home nestled in quaint village of Bozman with dock/pier for fishing, cr ...
From $975 per night (USD)Expedia
From $885 per night (USD)VRBO
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD Short Term Rental License #STRN-23-12 Arrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5- ...
From $885 per night (USD)VRBO
From $1075 per night (USD)Expedia
Breathtaking Waterfront Estate
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with its own 750ft shoreline, 75ft private d ...
From $1075 per night (USD)Expedia
From $789 per night (USD)VRBO
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $789 per night (USD)VRBO
From $763 per night (USD)Expedia
Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore ...
From $763 per night (USD)Expedia
From $300 per night (USD)VRBO
Romantic Waterfront Cottage with Amazing Sunsets
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located on the Chesapeake Bay side of Tilghman Island, our beautiful property is host to several cottages (one, two and ...
From $300 per night (USD)VRBO
Click For PricingExpedia
NEW Listing WATERFRONT sleeps 10 5 bedrooms 4 1/2 bths - dock & pool STN-23-23
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
STN-23-23 - First time offered waterfront located on Boone Creek between Oxford and Easton. Home features 5 bedrooms - ...
Click For PricingExpedia
From $394 per night (USD)VRBO
Downtown Retreat with Bikes, Fire Pit & Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Just minutes from downtown St. Michaels, this stylish 2-bedroom retreat combines modern design with thoughtful ...
From $394 per night (USD)VRBO
From $797 per night (USD)VRBO
Secluded Waterfront Property on 3 acres with swimming pool and dock.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Open floor plan home with ample views of the Leadenham Creek. Salt water swimming pool overlooks 220 feet of shoreline ...
From $797 per night (USD)VRBO
From $1027 per night (USD)VRBO
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, close walk to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County Short-Term Rental License STN-23-2 Villa estates ...
From $1027 per night (USD)VRBO
From $241 per night (USD)Expedia
Harbor View Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including th ...
From $241 per night (USD)Expedia