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

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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 $601 per night (USD)
VRBO
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
STRN-23-22 BOOK WITH US AND RECEIVE A FREE BUSCHEL OF CRABS! Come enjoy the quaintness of Claiborne, MD, just 5 minutes ...
From $601 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 $329 per night (USD)
VRBO
The Middle Point Cabin in Saint Michaels
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Our Talbot County Short Term Rental License Number is: ST-634-EIN 2019 Talbot County requires a minimum 3 night booking ...
From $329 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Cottage at Goose Neck Point
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming newly renovated cottage at the end of a private drive. Direct access to the Tred Avon River. Spectacular view ...
From $521 per night (USD)
VRBO
From $2383 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Only a 15 Minute Drive to Downtown St. Michaels and Easton! Jewel of the Tred Avon | an ESVR property This 7,700 sq ft ...
From $2383 per night (USD)
VRBO
Click For Pricing
Expedia
The Yellow Victorian in Historic Cambridge – Walk to Everything!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
The best kept little secret! Historic Cambridge, less than 2hours from DC/VA and 1 hour to the beach. House is located j ...
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
From $705 per night (USD)
Expedia
Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Summary: Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore ...
From $705 per night (USD)
Expedia
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
From $825 per night (USD)
VRBO
Tuckaway Cove. Book your fall get away now. New kitchen 2025
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Tucked away on a beautiful, quiet cove off the Miles River, with a large yard for playing, a private pool & dock, & kaya ...
From $825 per night (USD)
VRBO
$ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY$
From $1406 per night (USD)
VRBO
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)
VRBO
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 $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
From $360 per night (USD)
VRBO
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)
VRBO
From $1075 per night (USD)
Expedia
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)
Expedia
From $754 per night (USD)
VRBO
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $754 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 $407 per night (USD)
Expedia
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)
Expedia
From $432 per night (USD)
VRBO
Historic Renovated Jackrabbit Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Make some memories at this unique and family-friendly 19th Century farmhouse. Relax, ride bikes a few short blocks to th ...
From $432 per night (USD)
VRBO
From $813 per night (USD)
Expedia
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 $813 per night (USD)
Expedia
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 $1101 per night (USD)
Expedia
Thorneton Point Estate
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Summary: **HEATABLE SPA** Nestled on the tip of an idyllic private 5 acre peninsula, minutes from historic St. Michaels, ...
From $1101 per night (USD)
Expedia
From $966 per night (USD)
VRBO
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 $966 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 $949 per night (USD)
VRBO
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Escape to our 4-bedroom vacation home in Easton, just a 5-7 minute drive from the renowned St. Michaels. Immerse yoursel ...
From $949 per night (USD)
VRBO
From $1534 per night (USD)
Expedia
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)
Expedia
From $716 per night (USD)
VRBO
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)
VRBO
From $866 per night (USD)
VRBO
House close to Great Marsh Park and Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Two story Three bedroom house on tree line street half block from Great Marsh Park and Choptank River walking distance t ...
From $866 per night (USD)
VRBO
$Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30$
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 $925 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 $925 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
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 $1325 per night (USD)
VRBO
Gorgeous Waterfront
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Beautiful waterfront home - well furnished large open house, great amenities including pool, game room and gym, Sonos so ...
From $1325 per night (USD)
VRBO
From $307 per night (USD)
VRBO
Relax or Play on the Choptank River!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $307 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 $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
From $249 per night (USD)
VRBO
The Anchorage B&B - The Bounty
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $249 per night (USD)
VRBO
From $1022 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was d ...
From $1022 per night (USD)
Expedia
From $907 per night (USD)
VRBO
Waterfront Home on Chesapeake Bay with Dock, Bikes & Sunset Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Escape to the quiet charm of Tilghman Island at this bright, open-concept waterfront home. Located directly on ...
From $907 per night (USD)
VRBO
From $612 per night (USD)
Expedia
AUGUST Bookings, 15% Off. Near St.Michaels/Easton Waterfront, Dock,Hot Tub.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Another Luxury VIP Vacation Rental Property on the eastern shore. License # STRN-22-25 Stay at this comfortable propert ...
From $612 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
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $687 per night (USD)
VRBO
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)
VRBO
From $695 per night (USD)
Expedia
Tilghman | Pool | Private Dock | Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Talbot County STR License# STRN-22-1 Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and ...
From $695 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 $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 $1279 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 $1279 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 $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 $454 per night (USD)
Expedia
Downtown Oxford | Charming | Pet Friendly | Bikes
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming Cottage in the heart of Oxford, within walking distance to all our favorite Oxford things! We call this circa 1 ...
From $454 per night (USD)
Expedia
From $557 per night (USD)
VRBO
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 $557 per night (USD)
VRBO
From $295 per night (USD)
Expedia
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)
Expedia
From $757 per night (USD)
VRBO
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming Waterfront Cottage in St Michaels Begin your day at Riverview Retreat with a beautiful sunrise and be amazed wi ...
From $757 per night (USD)
VRBO
From $1053 per night (USD)
Expedia
Baydream Believer
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
BAYDREAM BELIEVER This home is a waterfront wonderland with plenty to do, from tubin ...
From $1053 per night (USD)
Expedia
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 $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 $294 per night (USD)
Expedia
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Welcome to Flat 207, your private retreat in the heart of beautiful St. Michaels. Located just steps from the h ...
From $294 per night (USD)
Expedia
From $1100 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 $1100 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 $430 per night (USD)
VRBO
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)
VRBO
From $555 per night (USD)
VRBO
The Water's Edge Rental Cambridge, Md - sleeps 10, 4 bedrooms
Bedrooms:
0
Bathrooms:
4
Sleeps:
10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $555 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 $640 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 $640 per night (USD)
VRBO
From $353 per night (USD)
Expedia
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)
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 $2167 per night (USD)
Expedia
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)
Expedia
From $284 per night (USD)
VRBO
Modern room with walk in shower and kitchenette
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
B&B Use Permit No. BB 19-04 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal ...
From $284 per night (USD)
VRBO
Click For Pricing
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
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VRBO
Upgraded King at Boutique Hotel, Private Beach, Walk to Restaurants & Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and ...
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VRBO
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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 $523 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is fully visi ...
From $523 per night (USD)
VRBO
From $1228 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 $1228 per night (USD)
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 $267 per night (USD)
Expedia
Stylish Home on the Choptank River (with Tidal Beach)
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Welcome to the River House! Stay in our renovated salt-box style home on the Choptank River of Maryland's Eastern Shore, ...
From $267 per night (USD)
Expedia
From $536 per night (USD)
VRBO
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)
VRBO
From $1046 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Kayaks | Pool | Private Dock
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Built in 1800, this 5-bedroom, 3-bathroom historic colonial shore house sits on 3.5+ acres and boasts endless nautical a ...
From $1046 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
From $661 per night (USD)
VRBO
Choptank River Beach Home w/ Pier in Cambridge!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Riverfront Location | In-Unit Washer & Dryer | Gas Grill for Group Cookouts Your next waterfront retreat awaits at thi ...
From $661 per night (USD)
VRBO
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 $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 $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 $206 per night (USD)
VRBO
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax in this quiet, renovated bungalow just a short bike ride to Tuckahoe State Park, the Eastern Shore's largest state ...
From $206 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 $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 $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 $1185 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 $1185 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
$Harbor View Suite\nTalbot County License Number STRN-25-58$
From $258 per night (USD)
Expedia
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)
Expedia

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