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 $951 per night (USD)
VRBO
Waterfront Home with Pool & Pet Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Wake up to waterfront living - toss crab pot off the dock in the morning & steam your catch for dinner. Spend a ...
From $951 per night (USD)
VRBO
From $782 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location , Location, Location Escape to this stunning cedar Lindal home on the Eastern Shore, just a short drive from h ...
From $782 per night (USD)
Expedia
From $1301 per night (USD)
VRBO
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 $1301 per night (USD)
VRBO
From $1300 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 $1300 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Brand New Pool and Hot Tub Coming June 2024 This 2-bedroom, 2-bathroom waterfront getaway features a character-filled i ...
From $533 per night (USD)
VRBO
From $374 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 $374 per night (USD)
Expedia
From $470 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 $470 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Waterfront Home w/ Hot Tub in Bozman Village!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5 ...
From $356 per night (USD)
Expedia
From $880 per night (USD)
VRBO
Secluded 1870s farmhouse full of historic charm + breathtaking waterfront views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This secluded 1870s farmhouse is full of historic charm and surrounded by natural beauty. Take in breathtaking views of ...
From $880 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Stay 3 Nights, Save 15% - Walk to Town
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Easy walking and biking distance to the heart of St. Michaels. Enjoy shops, restaurants, and waterfront charm j ...
From $374 per night (USD)
Expedia
$Charming 3-bedroom in Village of Claiborne \nwith continental breakfast STR24-33$
From $346 per night (USD)
VRBO
Charming 3-bedroom in Village of Claiborne \nwith continental breakfast STR24-33
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the beauty of Claiborne and feel the calm from this 3-bedroom house. With 2 queen beds, 1 full bed, and 1 twin ...
From $346 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 $236 per night (USD)
Expedia
Cottage #9 Stateroom located under main home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
OPEN March 25th to Nov 1st. Each year. State Room has no kitchen is located under main house, consist of small dining ta ...
From $236 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Cottage #6 Wild Goose on the left of Main House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
OPEN March 25th to Nov 1st. No6) Wild goose located to left of main house, consist of full Kitchen, dining table, queen ...
From $319 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Charming Well Priced Home Minutes From St Michaels
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Traveling to the shore for a friends & family event? Looking for a cozy well priced option? Centrally located b ...
From $247 per night (USD)
Expedia
From $417 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 $417 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 $394 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 $394 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Cottage #1 Lighthouse First Cottage down driveway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
OPEN March 25th until October 31st each year. No 1 is First cottage down drive has a full Kitchen, dining table, queen s ...
From $276 per night (USD)
Expedia
From $912 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 $912 per night (USD)
VRBO
From $751 per night (USD)
VRBO
St Michaels Retreat, Log Cabin, Family & Pet-Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4th of July Availability!! If you enjoy the old-fashioned fireworks, ice cream and BBQ picnic- Independence day celebra ...
From $751 per night (USD)
VRBO
From $212 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 $212 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Studio in Downtown – Walk to Everything!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Spring and Summer weekends are filling fast with guest coming to explore our fabulous little town. Welcome ...
From $294 per night (USD)
Expedia
From $670 per night (USD)
VRBO
An Afternoon Nap in the Hammock is a Must.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This beautiful home is minutes from historic St Michaels. Enjoy your morning coffee on the covered deck. Days c ...
From $670 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 $758 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 $758 per night (USD)
VRBO
From $980 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 $980 per night (USD)
Expedia
From $824 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 $824 per night (USD)
VRBO
From $1446 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 $1446 per night (USD)
VRBO
From $849 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 $849 per night (USD)
VRBO
From $1091 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 $1091 per night (USD)
Expedia
From $322 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 $322 per night (USD)
VRBO
From $748 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 $748 per night (USD)
VRBO
From $186 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 $186 per night (USD)
VRBO
From $693 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 $693 per night (USD)
Expedia
From $437 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 $437 per night (USD)
VRBO
From $558 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 $558 per night (USD)
Expedia
From $647 per night (USD)
VRBO
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 $647 per night (USD)
VRBO
From $301 per night (USD)
Expedia
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 $301 per night (USD)
Expedia
From $403 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 $403 per night (USD)
VRBO
From $2474 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 $2474 per night (USD)
Expedia
From $730 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 $730 per night (USD)
VRBO
From $2854 per night (USD)
Expedia
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. ...
From $2854 per night (USD)
Expedia
From $1449 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 $1449 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $666 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 $666 per night (USD)
VRBO
From $989 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 $989 per night (USD)
Expedia
From $993 per night (USD)
VRBO
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 $993 per night (USD)
VRBO
From $535 per night (USD)
Expedia
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 $535 per night (USD)
Expedia
From $1377 per night (USD)
VRBO
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)
VRBO
From $845 per night (USD)
Expedia
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to our 4-bedroom vacation home in Easton, just a 5-7 minute drive from the renowned St. Michaels. Immerse yoursel ...
From $845 per night (USD)
Expedia
From $1436 per night (USD)
VRBO
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 $1436 per night (USD)
VRBO
From $432 per night (USD)
Expedia
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)
Expedia
From $1058 per night (USD)
VRBO
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 $1058 per night (USD)
VRBO
From $1629 per night (USD)
Expedia
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Bedrooms:
6
Bathrooms:
7
Sleeps:
12
Talbot County STR License STRN-23-10 This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a spa-l ...
From $1629 per night (USD)
Expedia
From $1287 per night (USD)
VRBO
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 $1287 per night (USD)
VRBO
From $688 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 $688 per night (USD)
Expedia
From $1410 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 $1410 per night (USD)
VRBO
From $414 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 $414 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $188 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 $188 per night (USD)
VRBO
From $245 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 $245 per night (USD)
VRBO
From $277 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 $277 per night (USD)
VRBO
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 $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 $465 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 $465 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
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
$Cozy 2BR Home near Idlewild Park\n$
From $391 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 $391 per night (USD)
Expedia
From $4052 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 $4052 per night (USD)
VRBO
$\Point of View\ Waterfront cottage with panoramic views on Tilghman Island$
From $371 per night (USD)
Expedia
\"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 $371 per night (USD)
Expedia
From $835 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 $835 per night (USD)
VRBO
From $837 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 $837 per night (USD)
VRBO
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 $942 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 $942 per night (USD)
Expedia
From $383 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 $383 per night (USD)
VRBO
From $614 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 $614 per night (USD)
VRBO
From $1045 per night (USD)
VRBO
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 $1045 per night (USD)
VRBO
From $295 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 $295 per night (USD)
Expedia
From $597 per night (USD)
VRBO
JULY/AUGUST SPECIAL Book 4 nights, get 4th Night @ 30% discount
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
License # STRN-24-69...(3 night minimum off season.) A long, driveway on two, private acres, leads to this updated and c ...
From $597 per night (USD)
VRBO
From $264 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 $264 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $820 per night (USD)
Expedia
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 $820 per night (USD)
Expedia
From $313 per night (USD)
VRBO
The heart of St Michaels awaits.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Nestled in the vibrant heart of the St. Michaels historic district, this stunning one-bedroom, one-and-a-half-b ...
From $313 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Waterfront 3-Bedroom Cottage and Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Located in a quiet, secluded spot, it’s the perfect setting to disconnect and enjoy quality time with loved one ...
From $483 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Book a Week-Long Stay get a Crab Feast on Us!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Book a week-long stay in June, July or August and enjoy a crab feast on us! Experience the best of Tilghman Isl ...
From $609 per night (USD)
VRBO
From $670 per night (USD)
VRBO
Rent 4 Nites, 5th Nite FREE! Waterfront, Dock, Hot Tub, Oxford Ferry.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Another Luxury VIP Vacation Rental Property License # STRN-22-25 Stay at this comfortable property minutes from the qu ...
From $670 per night (USD)
VRBO
From $1268 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 $1268 per night (USD)
VRBO
From $918 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 $918 per night (USD)
Expedia
From $1009 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 $1009 per night (USD)
VRBO
From $2105 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 $2105 per night (USD)
Expedia
From $912 per night (USD)
VRBO
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $912 per night (USD)
VRBO
From $856 per night (USD)
Expedia
Relax by the Water - Summer Dates Available!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Summary: STRN-24-62. Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vaca ...
From $856 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Charming Stay, Just Minutes from Downtown!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: A stylish home that has all one needs for a fabulous getaway. Our quaint town has a bustling main street filled ...
From $451 per night (USD)
VRBO
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 $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 $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 $261 per night (USD)
VRBO
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 $261 per night (USD)
VRBO
From $1312 per night (USD)
Expedia
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Bedrooms:
5
Bathrooms:
5
Sleeps:
18
Choptank oasis offers the perfect Eastern Shore experience: 200' pier great for crabbing and fishing, river kayaking/ca ...
From $1312 per night (USD)
Expedia

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Results: 236 Rentals