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From $407 per night (USD)
VRBO
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The house is a 2 bedroom 2 ...
From $407 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $360 per night (USD)
Expedia
From $1075 per night (USD)
VRBO
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
TREMEZZO STAY - RANCH AT ROYAL OAK Our properties are owned, managed, and hosted by us. We deliver personally hosted lu ...
From $1075 per night (USD)
VRBO
From $1550 per night (USD)
Expedia
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Fantastic Family Compound Just 1/2 Mile to Historic District! Located just on the outskirts of St. Michaels, this fanta ...
From $1550 per night (USD)
Expedia
Click For Pricing
VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
Bedrooms:
5
Bathrooms:
5
Sleeps:
9
Eastern Shore Vacation Rentals presents The Water House. Beautifully appointed with artwork and antiques, The Water Hous ...
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VRBO
From $687 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Charming Waterfront Cottage Within Minutes to Historic St. Michaels. Kayaks and Bikes Included! Comfortably furnished an ...
From $687 per night (USD)
Expedia
From $763 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Easy, One-Level Living Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play ...
From $763 per night (USD)
VRBO
From $735 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Great location with plenty of room for friends and family. Wonderful outdoor spaces to enjoy! This little gem on the ban ...
From $735 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Dollhouse in Central Historic St Michaels
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Dollhouse is a fully updated two story centrally located 1870s historic house with 2 bedrooms and 1.5 baths. The ho ...
From $295 per night (USD)
VRBO
From $626 per night (USD)
Expedia
St. Michaels Waterfront Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful waterfront home sits just over the bridge entering St. Michaels in a prime location. Breathtaking waterf ...
From $626 per night (USD)
Expedia
From $359 per night (USD)
VRBO
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $359 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The recently restored historic Washington Melson House, located at 206 Locust St. is a 2 bedroom vacation cottage that i ...
From $304 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Walk to Everything House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The historic house which was restored from 2016-2020, is conveniently located on a quiet street near the Blue Crab coffe ...
From $353 per night (USD)
VRBO
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Expedia
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Location in Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your own private condo-style Junior Suite, and suite cottage at Sandaway Suites & Beach in Oxford, MD. Please note ...
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Expedia
From $685 per night (USD)
VRBO
Waterfront Property, kayaks, private dock, near town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cranford on the Miles is an historic waterfront home located on 3+ acres, in St. Michaels, and 1+ mile from the beginnin ...
From $685 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 $1119 per night (USD)
VRBO
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)
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 $409 per night (USD)
VRBO
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)
VRBO
From $676 per night (USD)
Expedia
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)
Expedia
From $1002 per night (USD)
VRBO
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
TREMEZZO STAY - SPENCER CREEK CABIN Our properties are owned, managed, and hosted by us. We deliver personally hosted ...
From $1002 per night (USD)
VRBO
Click For Pricing
Expedia
Town View King Apartment with Private Beach - Walk to shops and restaurants
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy our Chesapeake Bay Vacations rental in charming Oxford, Maryland! Sandaway Suites & Beach in Oxford, MD is an excl ...
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Expedia
From $2167 per night (USD)
VRBO
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 12 adults. Located on ...
From $2167 per night (USD)
VRBO
From $1173 per night (USD)
VRBO
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Ingleton! EARLY CHECKIN AND LATECHECKOUT OCTOBER. Relax by the pool. Fish or crab or picnic at the end of t ...
From $1173 per night (USD)
VRBO
From $370 per night (USD)
VRBO
Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Waterfront, 2 bedroom, 2 bath Private Cottage on Solitude Creek. 3.4 miles to St. Michaels and Oxford; 1 1/2 hours to O ...
From $370 per night (USD)
VRBO
From $407 per night (USD)
Expedia
Stunning views at WATERFRONT St Michaels area historic home, dog friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Full renovations completed in 2016 on this historic home. Sleeps four (1 King, 1 Queen, 1 Twin). Kick back, relax and e ...
From $407 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Perfect Waterview Cottage - St. Michaels Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipwright Cottage is a fully-renovated idyllic getaway located in the Bay Hundred area of the Chesapeake Bay just 8 mil ...
From $248 per night (USD)
VRBO
From $1062 per night (USD)
VRBO
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Relax and absorb the beauty of living on the water at our 23 acre waterfront property on Harris Creek, in between histor ...
From $1062 per night (USD)
VRBO
From $495 per night (USD)
VRBO
BOOK NOW FOR SPRING & SUMMER DATES.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
STN-22-40 ONE OF OUR MOST SOUGHT AFTER PROPERTIES! MINUTES FROM ST. MICHAELS...... Peaceful retreat with breathtaking su ...
From $495 per night (USD)
VRBO
From $256 per night (USD)
Expedia
Relaxing Waterfront Cottage Near St Michaels, Maryland
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Eastern Shore two bedroom cottage with dock on a quiet creek of the Chesapeake Bay in Wittman, Maryland. Surrounded by ...
From $256 per night (USD)
Expedia
From $1485 per night (USD)
VRBO
Beautiful Tidewater home between Easton & ST Michaels!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Quintessential charming Eastern Shore waterfront home stocked with all the amenities to make your stay stress free and ...
From $1485 per night (USD)
VRBO
From $824 per night (USD)
VRBO
Luxurious waterfront home - Cèilidh
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Beautiful luxury waterfront home in historic downtown Oxford. A rare find with 2 piers, Beautiful luxury waterfront home ...
From $824 per night (USD)
VRBO
From $425 per night (USD)
VRBO
Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Located on the Chesapeake Bay side of Tilghman Island, this beautiful two-story, three bedroom cottage is available for ...
From $425 per night (USD)
VRBO
From $509 per night (USD)
VRBO
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated one story home directly on the water. Gorgeous hickory floors. Open layout for entertaining. Din ...
From $509 per night (USD)
VRBO
From $851 per night (USD)
VRBO
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
All persons thinking about making a newbooking, should consider adding travel cancellation insurance, prior to booking. ...
From $851 per night (USD)
VRBO
From $506 per night (USD)
VRBO
House on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Talbot County License STRN-23-41 Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from th ...
From $506 per night (USD)
VRBO
From $1534 per night (USD)
VRBO
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Bedrooms:
9
Bathrooms:
8
Sleeps:
12
TREMEZZO STAY - CHEASAPEAKE MANSION Our properties are owned, managed, and hosted by us. We deliver personally hosted l ...
From $1534 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Step into history without sacrificing modern comforts. Combsberry is a 1730 waterfront estate nestled on 30 pri ...
From $716 per night (USD)
Expedia
$Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30$
From $584 per night (USD)
VRBO
Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Offering a HOMEY rental on the gorgeous Chesapeake Bay - Leadenham Creek, Bozman, MD. The Gnome Home is nestled on 3 1 ...
From $584 per night (USD)
VRBO
From $1179 per night (USD)
VRBO
Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings **IMPORTA ...
From $1179 per night (USD)
VRBO
From $1034 per night (USD)
VRBO
Historic Oxford Waterfront Estate
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Bonfield Manor is located at the entrance of Oxford, a half-mile walk or bike ride to restaurants, shops and the Rivervi ...
From $1034 per night (USD)
VRBO
From $765 per night (USD)
VRBO
St. Michael's Premier In-Town Rental with heated pool.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
As Saint Michael's Premier STR, we take this title very seriously, so read on to see what we've done this off season. H ...
From $765 per night (USD)
VRBO
From $816 per night (USD)
VRBO
September Splender! Waterfront ,Pool, Dock, Hot Tub.A Luxury VIP Vacation Rental
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
License No. STRN-24-4 Note: A Contract is Required to Be Signed This lovely home offers a large main house and a privat ...
From $816 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Charming cottage along water with private pier, near St. Michaels Winery
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
In the delightful town of Bozman lies a snug, welcoming 1-bedroom cottage perfect for your upcoming holiday. As you step ...
From $270 per night (USD)
VRBO
From $478 per night (USD)
VRBO
SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
ST-605-JOH Upon arrival you realize this is the Eastern Shore Experience you have been looking for......A gated garden ...
From $478 per night (USD)
VRBO
$ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY$
From $1406 per night (USD)
Expedia
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Talbot County MD License #STRN-24-89 - The Cove At St. Michaels is a magnificent 15.5 acre estate property with ingrou ...
From $1406 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Less than a mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore esca ...
From $327 per night (USD)
VRBO
From $631 per night (USD)
VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Bedrooms:
3
Bathrooms:
6
Sleeps:
9
The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been re ...
From $631 per night (USD)
VRBO
From $311 per night (USD)
VRBO
Stay in the HEART of Saint Michaels!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stunning and completely renovated 1940s bungalow in the heart of Saint Michaels! Located just steps from shopping, resta ...
From $311 per night (USD)
VRBO
From $931 per night (USD)
VRBO
Private Retreat with HUGE Water Views!!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Wonderful large family home on Harris Creek. With 6 bedrooms and 3 full bathrooms (including master bedroom suite), th ...
From $931 per night (USD)
VRBO
From $1805 per night (USD)
VRBO
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)
VRBO
From $324 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 $324 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 $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 $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 $1296 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 $1296 per night (USD)
Expedia
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
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 $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 $194 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 $194 per night (USD)
VRBO
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
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 $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 $1077 per night (USD)
VRBO
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 $1077 per night (USD)
VRBO
From $301 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 $301 per night (USD)
VRBO
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 $536 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 $536 per night (USD)
Expedia
From $661 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 $661 per night (USD)
VRBO
From $357 per night (USD)
Expedia
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)
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 $1100 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 $1100 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 $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
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 $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 $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
$Cozy 2BR Home near Idlewild Park\n$
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 $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 $1549 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 $1549 per night (USD)
Expedia
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 $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 $925 per night (USD)
VRBO
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 $925 per night (USD)
VRBO
From $430 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 $430 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 $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
$Harbor View Suite\nTalbot County License Number STRN-25-58$
From $258 per night (USD)
VRBO
Harbor View Suite\nTalbot County License Number STRN-25-58
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 $258 per night (USD)
VRBO
From $805 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 $805 per night (USD)
VRBO
From $1228 per night (USD)
VRBO
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 $1228 per night (USD)
VRBO
Click For Pricing
Expedia
Historic 1918 House 1/2 Block from the Choptank River
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
This old fisherman's home in the historic district of Cambridge has been recently renovated and is close to restaurants, ...
Click For Pricing
Expedia
From $404 per night (USD)
VRBO
Beautiful Colonial Home on the Choptank River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to this newly updated 4-bedroom, 2-bath colonial home for a fun-filled retreat on the Cambridge coast! Offering k ...
From $404 per night (USD)
VRBO
$\Belle Aire Landing\ a Large Beautiful Waterfront Estate! Under New Management!$
From $2014 per night (USD)
Expedia
\"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)
Expedia
$The Drinking Gourd: \nStunning Penthouse in Historic Downtown Cambridge$
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
$Aurora Blue - A Stylish Experience \n$
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 $265 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 $265 per night (USD)
VRBO
From $545 per night (USD)
VRBO
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $545 per night (USD)
VRBO

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Results: 113 Rentals