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 $214 per night (USD)
VRBO
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 $214 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
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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 $329 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 $329 per night (USD)
Expedia
From $1016 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 $1016 per night (USD)
VRBO
From $610 per night (USD)
Expedia
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)
Expedia
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 $366 per night (USD)
Expedia
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 $366 per night (USD)
Expedia
From $797 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 $797 per night (USD)
VRBO
From $265 per night (USD)
Expedia
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 $265 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 $785 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 $785 per night (USD)
Expedia
From $1549 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 $1549 per night (USD)
VRBO
From $517 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 $517 per night (USD)
VRBO
From $549 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 $549 per night (USD)
VRBO
From $727 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 $727 per night (USD)
Expedia
From $1251 per night (USD)
VRBO
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 $1251 per night (USD)
VRBO
From $282 per night (USD)
VRBO
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 $282 per night (USD)
VRBO
From $1177 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 $1177 per night (USD)
VRBO
$Charming 4 bedroom in Historic Cambridge\n\n$
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 $197 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 $197 per night (USD)
VRBO
$Cozy 2BR Home near Idlewild Park\n$
From $437 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 $437 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
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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 ...
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VRBO
From $562 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 $562 per night (USD)
VRBO
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
From $394 per night (USD)
VRBO
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 $394 per night (USD)
VRBO
From $690 per night (USD)
Expedia
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 $690 per night (USD)
Expedia
From $296 per night (USD)
VRBO
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 $296 per night (USD)
VRBO
From $723 per night (USD)
Expedia
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 $723 per night (USD)
Expedia
From $1411 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 $1411 per night (USD)
VRBO
From $1119 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 $1119 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 $261 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 $261 per night (USD)
VRBO
From $1296 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 $1296 per night (USD)
VRBO
From $1033 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 $1033 per night (USD)
VRBO
From $567 per night (USD)
VRBO
Escape to Nature at Wales Family Cabin
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Step away from the rush of everyday life and into the calm of our log-built woodland retreat. Nestled on acres of prist ...
From $567 per night (USD)
VRBO
From $409 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 $409 per night (USD)
Expedia
From $1362 per night (USD)
VRBO
Waterfront Cottage Retreat on 18 Acre Farm, Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Our newly renovated point cottage is nestled on an 18 acre waterfront private retreat with access to a swimming ...
From $1362 per night (USD)
VRBO
From $927 per night (USD)
VRBO
Newly Renovated Summer Paradise-Pool-Tennis-Garden Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Our newly renovated garden cottage is nestled on an 18 acre waterfront private retreat with access to a swimmin ...
From $927 per night (USD)
VRBO
From $2658 per night (USD)
VRBO
Waterfront Farmhouse Retreat on 18 Acres, Pool
Bedrooms:
7
Bathrooms:
8
Sleeps:
16
Summary: Our newly renovated Brick House is nestled on an 18 acre waterfront private retreat with access to a swimming p ...
From $2658 per night (USD)
VRBO
From $9892 per night (USD)
VRBO
Private Waterfront Retreat Center, New Reno on 18 Acres
Bedrooms:
25
Bathrooms:
25
Sleeps:
50
Summary: Our newly renovated 25 bedroom waterfront property is ideal for your next retreat. The house overlooks the beau ...
From $9892 per night (USD)
VRBO
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 $151 per night (USD)
VRBO
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 $151 per night (USD)
VRBO
From $240 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 $240 per night (USD)
VRBO
From $445 per night (USD)
Expedia
The Farm House at Hunting Creek
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Experience the charm of this stunning, gated estate carriage house, nestled on 80 acres of breathtaking land. With panor ...
From $445 per night (USD)
Expedia
From $373 per night (USD)
VRBO
Walk to Dtwn: Waterfront Eastern Shore Townhome!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Game Room | Scenic Waterfront Deck | Community Pool | Pet Friendly w/ Fee | EV Charger Experience life in the heart of ...
From $373 per night (USD)
VRBO
From $778 per night (USD)
Expedia
Waterfront | Pet Friendly & Close to St. Michaels
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Wake up to serene waterfront views, drop a crab pot from the dock, or sip coffee while the sun rises over the c ...
From $778 per night (USD)
Expedia
From $129 per night (USD)
VRBO
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Wye Mills is waiting for you at this awesome 1-bedroom cottage. With WiFi, heating, a washing machine, and more, guests ...
From $129 per night (USD)
VRBO
From $194 per night (USD)
Expedia
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 $194 per night (USD)
Expedia
$Aurora Blue - A Stylish Experience \n$
From $273 per night (USD)
VRBO
Aurora Blue - A Stylish Experience \n
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Stylish experience at the centrally located retreat. New owners purchased East and renovated the entire home both inside ...
From $273 per night (USD)
VRBO
From $872 per night (USD)
VRBO
Secluded 1870s farmhouse full of historic charm + breathtaking waterfront views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
This secluded 1870s farmhouse is full of historic charm and surrounded by natural beauty. Take in breathtaking views of ...
From $872 per night (USD)
VRBO
From $344 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 $344 per night (USD)
VRBO
From $343 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 $343 per night (USD)
VRBO
From $676 per night (USD)
VRBO
Beautiful 3-bedroom Miles River waterfront in tranquil Easton - Relax and unwind
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unwind in Easton at this beautiful newly refreshed waterfront home nestled in private cove on 47 acres of river and farm ...
From $676 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Walk to Park & River: Dog-Friendly Cambridge Gem
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Half-Mi to Historic Downtown | Covered Porch | Yard Space | Great Fishing Area Whether you’re here to explore Cambridge ...
From $177 per night (USD)
VRBO
From $808 per night (USD)
VRBO
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 $808 per night (USD)
VRBO
From $2152 per night (USD)
Expedia
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)
Expedia
From $331 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 $331 per night (USD)
VRBO
From $446 per night (USD)
Expedia
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 $446 per night (USD)
Expedia
From $268 per night (USD)
VRBO
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 $268 per night (USD)
VRBO
From $1011 per night (USD)
Expedia
Waterfront Paradise with Private Pool and Dock minutes from St Michaels
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Duck Duck Goose – Tag, you’re it! Escape to this extraordinary 6-bedroom, 7-bathroom waterfront retreat, where a class ...
From $1011 per night (USD)
Expedia
Click For Pricing
VRBO
Downtown St. Michaels | Porch + Pet-Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stay in the heart of St. Michaels at this stylish 3-bedroom retreat, just steps from boutique shops, waterfront ...
Click For Pricing
VRBO
From $347 per night (USD)
Expedia
Eastons Urban Oasis- centrally located townhome in Talbot County
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Unwind in Easton at this delightful townhome. With 3 cozy bedrooms, stainless steal appliances, and fresh upgrades, this ...
From $347 per night (USD)
Expedia
From $785 per night (USD)
VRBO
Nature`s Rest - Waterfront Serenity with Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover Nature`s Rest, a stunning 4-bedroom, 3-bathroom waterfront home where the name captures the heart of this peace ...
From $785 per night (USD)
VRBO

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Results: 167 Rentals