Talbot Area, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Talbot Area, Maryland on RentalSaver.com!

Talbot Area Rentals

From $626 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 $626 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 $711 per night (USD)
VRBO
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 $711 per night (USD)
VRBO
From $451 per night (USD)
Expedia
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 $451 per night (USD)
Expedia
From $1340 per night (USD)
VRBO
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Bedrooms:
5
Bathrooms:
7
Sleeps:
20
Treat yourself to this unique waterfront retreat where you’ll enjoy stunning ocean liner views of the Choptank River fro ...
From $1340 per night (USD)
VRBO
From $256 per night (USD)
VRBO
Cheerful three-bedroom Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Introducing River Light Cottage, the perfect escape in historic Cambridge, Maryland! A short walk from downtown shops an ...
From $256 per night (USD)
VRBO
From $907 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 $907 per night (USD)
VRBO
From $238 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 $238 per night (USD)
Expedia
From $174 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 $174 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Stylish Victorian in Historic District
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beware: not your typical VRBO A hunt has been set for you and your companions to follow the dramatized story of Eva Rob ...
From $407 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 $868 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 $868 per night (USD)
VRBO
From $1088 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 $1088 per night (USD)
Expedia
From $357 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 $357 per night (USD)
VRBO
From $1805 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Elegantly Appointed Estate with Fantastic Outdoor Areas Elegantly furnished and located in a prestigious estate area of ...
From $1805 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Eastern Shore Waterside Cottage Near St. Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to an idyllic retreat, nestled in the peaceful town of Neavitt, just a short drive from the charming village of ...
From $331 per night (USD)
VRBO
From $692 per night (USD)
Expedia
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 $692 per night (USD)
Expedia
From $998 per night (USD)
VRBO
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 $998 per night (USD)
VRBO
From $1022 per night (USD)
Expedia
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: Discover the ultimate Eastern Shore escape at The Farm at Bald Eagle Point—a private 6-bedroom waterfront estat ...
From $1022 per night (USD)
Expedia
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VRBO
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Vacation With No Limits! The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is created by a sprawling inte ...
Click For Pricing
VRBO
From $362 per night (USD)
Expedia
Quaint Tilghman Island home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Vacation home minutes from St Michaels. Tucked away on a quiet neighborhood street is the Wandering Loon. A pe ...
From $362 per night (USD)
Expedia
From $305 per night (USD)
VRBO
4-Bedroom Retreat: Modern, Pet-Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Heart of the Island & Pet Friendly Retreat on Tilghman Island! Step into a thoughtfully curated space where coa ...
From $305 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Eastern Shore Vacation Rentals presents Oyster Cottage. Just a 10-minute drive from historic St. Michaels and Tilghman I ...
From $624 per night (USD)
Expedia
From $762 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 $762 per night (USD)
VRBO
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Expedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Pool | Kayaks
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sha La La La … Fun For Everyone! The impressive 5BR, 3BA, 2 half BA waterfront along Irish Creek is designed with relax ...
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Expedia
From $271 per night (USD)
VRBO
Casual Bungalow close to Choptank River, sleeps 5
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A newly renovated pristine bungalow close to downtown Cambridge, MD. We are conveniently located near St. Michael, East ...
From $271 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 $2113 per night (USD)
VRBO
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)
VRBO
From $384 per night (USD)
Expedia
A little slice of heaven on the Choptank River Sept 19 to 23 is now open
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A perfect getaway on our waterfront property .You will have your own private beach. You can enjoy crabbing ,fishing , ka ...
From $384 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This newly renovated 3BR, 3BA Sherwood vacation home is designed with your comfort in mind. The free-flowing floor plan ...
From $491 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Newly Renovated Guest House located in Oxford MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Mary ...
From $238 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
From $289 per night (USD)
Expedia
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 $289 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $320 per night (USD)
Expedia
New listing! Riverside Retreat on the Choptank River
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview renta ...
From $320 per night (USD)
Expedia
From $1000 per night (USD)
VRBO
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 $1000 per night (USD)
VRBO
From $603 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 $603 per night (USD)
VRBO
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VRBO
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. ...
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VRBO
From $1452 per night (USD)
Expedia
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 $1452 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Magnificent Historic Home by Water is Ready!
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Our house, built in 1736, is ideally located in the heart of historic Cambridge. Facing the Choptank River, it is 1/2 bl ...
From $610 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 $392 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 $392 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 $370 per night (USD)
VRBO
Luxury on the river, steps to downtown &boat ramp!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Beautifully crafted 1915 Sailmakers home nestled perfectly off the choptank harbor. Newly renovated with stunning appoin ...
From $370 per night (USD)
VRBO
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Expedia
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 - ...
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Expedia
From $375 per night (USD)
VRBO
High Water Guest House<br>
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of h ...
From $375 per night (USD)
VRBO
From $804 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 $804 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy historic Cambridge all year at this fully stocked and freshly renovated 2 bedroom, 2.5 bath townhouse across the s ...
From $371 per night (USD)
VRBO
From $264 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 $264 per night (USD)
Expedia
$\Point of View\ Waterfront cottage with panoramic views on Tilghman Island$
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 $233 per night (USD)
Expedia
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 $233 per night (USD)
Expedia
From $422 per night (USD)
VRBO
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)
VRBO
From $873 per night (USD)
Expedia
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 $873 per night (USD)
Expedia
From $598 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 $598 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 $742 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 $742 per night (USD)
VRBO
From $547 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 $547 per night (USD)
VRBO
From $496 per night (USD)
VRBO
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)
VRBO
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Expedia
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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Expedia
From $835 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 $835 per night (USD)
VRBO
From $1235 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
A Tranquil Contemporary St. Michaels Waterfront Cottage featuring a separate 1st floor newly renovated garage apartment ...
From $1235 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Brand New Pool, Hot Tub and Dock This 2-bedroom, 2-bathroom waterfront getaway features a character-filled interior and ...
From $558 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Retreat with family to this quiet and peaceful, 4-bedroom, 2.5-bathroom vacation rental in Trappe, Maryland. Relax on Ox ...
From $317 per night (USD)
Expedia
From $3687 per night (USD)
VRBO
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)
VRBO
From $1195 per night (USD)
Expedia
Heated pool, sandy beach, pier, and playground set punch point apart!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
TREMEZZO STAY - PUNCH POINT Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury re ...
From $1195 per night (USD)
Expedia
$Charming 4 bedroom in Historic Cambridge\n\n$
From $527 per night (USD)
VRBO
Charming 4 bedroom in Historic Cambridge\n\n
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Enjoy the old world charm of this home, built in 1894 in the historic district of the picturesque and diverse town of Ca ...
From $527 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 $297 per night (USD)
VRBO
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this fully renovated historic condo nestled in the heart of downtown Cambridge, Maryland, with its fabulous d ...
From $297 per night (USD)
VRBO
$Cozy 2BR Home near Idlewild Park\n$
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 $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 $454 per night (USD)
Expedia
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)
Expedia
From $339 per night (USD)
VRBO
Waterviews, Comfort & Convenience!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Looking for some rest or relief…or perhaps just a little fun? This home is just steps away from the Cambridge Yacht Basi ...
From $339 per night (USD)
VRBO
From $627 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 $627 per night (USD)
VRBO
From $288 per night (USD)
VRBO
Pet-Friendly Island Getaway | Bikes & Porch
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Experience the best of Tilghman Island in this bright and inviting 3-bedroom, 2-bath cottage. Perfect for famil ...
From $288 per night (USD)
VRBO
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $376 per night (USD)
Expedia
The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to The Drinking Gourd...a freshly renovated 2-bedroom penthouse in the heart of the historic downtown district o ...
From $376 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Minutes from Downtown Cambridge and Downtown Easton | 104+ Acre Farm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Farmhouse Surrounded by Nature This charming 4BR, 4BA vacation home with 104+/- acres on the Choptank River is the perf ...
From $681 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Waterfront House in Saint Michaels: Pets Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Escape to this charming 2-bedroom waterfront home in Saint Michaels! Enjoy a perfect blend of relaxation and co ...
From $328 per night (USD)
Expedia
From $790 per night (USD)
VRBO
Pet-Friendly 3 bedroom with a Pool, Hot Tub & Near St. Michaels
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Your perfect fall Chesapeake getaway awaits! Just minutes from the charming harbor town of St. Michaels, this 3 ...
From $790 per night (USD)
VRBO
$Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n$
From $207 per night (USD)
Expedia
Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Unwind in Wittman at this welcoming house. With 3 cozy bedrooms including a queen bed, full bed, and bunk bed, guests wi ...
From $207 per night (USD)
Expedia
From $1095 per night (USD)
VRBO
Ironman & Eagleman - 4-bedroom house in charming Cambridge.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This 4-bedroom house in Cambridge is perfect for your Eastern Shore experience. With 2 queen beds and 4 twin beds, guest ...
From $1095 per night (USD)
VRBO
From $1401 per night (USD)
Expedia
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 $1401 per night (USD)
Expedia
From $1007 per night (USD)
VRBO
Gorgeous retreat across from yacht club, the Choptank, and IronMan finish line!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The perfect location for an easy getaway in any season. The home is across the street from the IRONMAN Maryland finish l ...
From $1007 per night (USD)
VRBO
From $947 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Swan Hollow, a charming 3-bedroom, 2-full bathroom, 2-half bathroom tranquil retreat nestled down a picturesq ...
From $947 per night (USD)
Expedia
$\Belle Aire Landing\ a Large Beautiful Waterfront Estate! Under New Management!$
From $2014 per night (USD)
VRBO
\"Belle Aire Landing\" a Large Beautiful Waterfront Estate! Under New Management!
Bedrooms:
6
Bathrooms:
9
Sleeps:
22
*Under New Management for 2025!* When thinking about an amazing vacation, the words that come to mind should be like 'A ...
From $2014 per night (USD)
VRBO
From $480 per night (USD)
Expedia
Bateau Cabin one of three Cove Cabins in St Michaels
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover unparalleled relaxation and tranquility at The Bateau Cabin, our beautifully designed waterfront retreat. Locat ...
From $480 per night (USD)
Expedia
From $366 per night (USD)
VRBO
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)
VRBO
From $582 per night (USD)
Expedia
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 $582 per night (USD)
Expedia
From $250 per night (USD)
VRBO
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 $250 per night (USD)
VRBO
From $1163 per night (USD)
Expedia
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 $1163 per night (USD)
Expedia
From $505 per night (USD)
VRBO
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)
VRBO
From $848 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 $848 per night (USD)
VRBO
From $509 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 $509 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Wake up to sweeping Chesapeake Bay views just minutes from St. Michaels. Cast a line from your private dock, si ...
From $424 per night (USD)
Expedia
From $425 per night (USD)
VRBO
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 $425 per night (USD)
VRBO
From $1196 per night (USD)
Expedia
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 $1196 per night (USD)
Expedia
From $1257 per night (USD)
VRBO
Short drive to Downtown Cambridge | Private Dock | Guest House
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Bucolic and Serene NEW POOL COMING SOON! This charming 6BR, 3BA Victorian waterfront vacation home complimented by a 1B ...
From $1257 per night (USD)
VRBO
From $371 per night (USD)
Expedia
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 $371 per night (USD)
Expedia
Click For Pricing
VRBO
Charming 1-bedroom cottage in downtown Saint Michaels
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay comfortably in Saint Michaels at this 1-bedroom cottage. Nestled in a beautiful and peaceful setting, this brillian ...
Click For Pricing
VRBO
From $153 per night (USD)
Expedia
Cambridge Apt in Walkable Neighborhood
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Waterfront Setting | Close to Local Eats Explore the quiet side of the Chesapeake Bay with your closest travel buddy at ...
From $153 per night (USD)
Expedia

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