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From $1343 per night (USD)
VRBO
Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!
Bedrooms:
6
Bathrooms:
5
Sleeps:
16
WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings Discover ...
From $1343 per night (USD)
VRBO
From $683 per night (USD)
Expedia
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY!
Bedrooms:
4
Bathrooms:
3
Sleeps:
4
STRN-23-22 Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Easte ...
From $683 per night (USD)
Expedia
From $1049 per night (USD)
VRBO
Historic Oxford Waterfront Estate
Bedrooms:
6
Bathrooms:
7
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 $1049 per night (USD)
VRBO
$St. Michael's Premier In-Town Rental with heated pool-opens 4\/11\/2025$
From $813 per night (USD)
Expedia
St. Michael's Premier In-Town Rental with heated pool-opens 4\/11\/2025
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 $813 per night (USD)
Expedia
From $1012 per night (USD)
VRBO
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
License No. STRN-24-4 This lovely home offers a large main house and a private apartment over the attached garage. All ...
From $1012 per night (USD)
VRBO
From $270 per night (USD)
Expedia
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)
Expedia
From $398 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 $398 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 $2421 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
Bedrooms:
6
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 $2421 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Beautiful Colonial Home on the Choptank River
Bedrooms:
2
Bathrooms:
5
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 $446 per night (USD)
Expedia
From $296 per night (USD)
VRBO
The B&B of Anchorage - Skipjack
Bedrooms:
2
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 $296 per night (USD)
VRBO
From $876 per night (USD)
VRBO
Relax by the Water - Summer Dates Available!
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
This waterfront property offers a wonderful open floor plan. The well stocked kitchen is terrific for preparing meals to ...
From $876 per night (USD)
VRBO
From $536 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 $536 per night (USD)
VRBO
From $913 per night (USD)
Expedia
🦆Tuckaway Cove🦆 Private, relaxing waterfront property; close to everything!
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 $913 per night (USD)
Expedia
$ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY$
From $1406 per night (USD)
VRBO
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS\nPET FRIENDLY
Bedrooms:
7
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 $1127 per night (USD)
Expedia
Classic Eastern Shore Waterfront Manor House - ST-936
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Quintessential Eastern Shore experience on 30 acres 1.5 miles from downtown St. Michaels. Original house dates to the e ...
From $1127 per night (USD)
Expedia
From $429 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 $429 per night (USD)
VRBO
From $992 per night (USD)
Expedia
Indian Fields - 25-Acre Nature Lovers retreat!
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Indian Fields - Twenty-five acre nature lovers retreat! Pool, Kayaks, Fire Pit - The family Dog is Welcome! Bring your ...
From $992 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Bedrooms:
4
Bathrooms:
7
Sleeps:
9
The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels and has been re ...
From $700 per night (USD)
VRBO
From $316 per night (USD)
Expedia
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 $316 per night (USD)
Expedia
From $893 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 $893 per night (USD)
VRBO
From $651 per night (USD)
Expedia
Crabby Casa; Waterfront with pool and dock on the Choptank River in Cambridge MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Create unforgettable memories by reserving your riverside retreat today! The primary bedroom features a luxurious king ...
From $651 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $365 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Cottage on Cabin Creek
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The cottage is the perfect place for a couple's get away. The views of Cabin Creek are stunning. You will enjoy beautifu ...
From $278 per night (USD)
Expedia
From $1832 per night (USD)
VRBO
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Bedrooms:
6
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 $1832 per night (USD)
VRBO
$Two Oysters House 2025 Remodel waterfront w\/ pool in St. Michaels$
From $936 per night (USD)
Expedia
Two Oysters House 2025 Remodel waterfront w\/ pool in St. Michaels
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private ...
From $936 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Jellyfish 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 $513 per night (USD)
Expedia
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautifully renovated one story home directly on the water. Gorgeous hickory floors. Open layout for entertaining. Din ...
From $513 per night (USD)
Expedia
From $1518 per night (USD)
VRBO
Luxury Waterfront with pool and deep water dock, minutes from St Michaels.
Bedrooms:
5
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 $1518 per night (USD)
VRBO
From $415 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 $415 per night (USD)
Expedia
From $478 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 $478 per night (USD)
VRBO
From $923 per night (USD)
Expedia
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Bedrooms:
4
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 $923 per night (USD)
Expedia
From $2933 per night (USD)
VRBO
Waterfront-Private 153 acre Historic Estate
Bedrooms:
7
Bathrooms:
11
Sleeps:
12
We open our gates and invite you in to the very exclusive, one of a kind experience at historic Langdon Estate. This pre ...
From $2933 per night (USD)
VRBO
From $859 per night (USD)
Expedia
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
All persons thinking about making a newbooking, should consider adding travel cancellation insurance, prior to booking. ...
From $859 per night (USD)
Expedia
From $1525 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 $1525 per night (USD)
VRBO
From $1643 per night (USD)
Expedia
Breathtaking Waterfront Estate
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Summary: Durham-Hythe Estate is nestled within 7.5 acres of idyllic grounds with its own 750ft shoreline, 75ft private d ...
From $1643 per night (USD)
Expedia
From $561 per night (USD)
VRBO
House on the Chesapeake Bay
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Talbot County License STRN-23-41 Enjoy the beauty of the Chesapeake Bay on Tilghman Island. Enjoy fresh seafood from th ...
From $561 per night (USD)
VRBO
From $768 per night (USD)
Expedia
Waterfront 4 acre home with pool between the towns of St. Michaels & Easton!
Bedrooms:
4
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 $768 per night (USD)
Expedia
$Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT\/30 ACRES\/HUGE POLYWOOD PLAYGROUND$
From $1979 per night (USD)
VRBO
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT\/30 ACRES\/HUGE POLYWOOD PLAYGROUND
Bedrooms:
10
Bathrooms:
8
Sleeps:
12
TREMEZZO STAY - CHEASAPEAKE MANSION Our properties are owned, managed, and hosted by us. We deliver personally hosted l ...
From $1979 per night (USD)
VRBO
From $1051 per night (USD)
VRBO
Pet-Friendly Stay with Pool – Relax & Unwind!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
The living spaces boast original architectural features, from soaring ceilings to ornate moldings, creating an ambiance ...
From $1051 per night (USD)
VRBO
From $874 per night (USD)
VRBO
House close to Great Marsh Park and Downtown
Bedrooms:
2
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 $874 per night (USD)
VRBO
$Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30$
From $631 per night (USD)
Expedia
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 $631 per night (USD)
Expedia
$Waterfront - pier & acreage to run & play. Pet friendly Oct\/Nov dates open!$
From $918 per night (USD)
VRBO
Waterfront - pier & acreage to run & play. Pet friendly Oct\/Nov dates open!
Bedrooms:
3
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)
VRBO
$Historic 1918 House 1\/2 Block from the Choptank River$
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 $1622 per night (USD)
VRBO
Beautiful Tidewater home between Easton & ST Michaels!
Bedrooms:
7
Bathrooms:
4
Sleeps:
8
Quintessential charming Eastern Shore waterfront home stocked with all the amenities to make your stay stress free and ...
From $1622 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Little Creek Hideaway - Privacy and Perfect Family Getaway.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Come relax at Little Creek Hideaway, the perfect family getaway during any season. Located just 10 minutes from Easton, ...
From $319 per night (USD)
Expedia
From $753 per night (USD)
VRBO
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This beautifully decorated Harris Creek waterfront home is waiting for you! With plenty of room for multiple families to ...
From $753 per night (USD)
VRBO
From $745 per night (USD)
Expedia
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Recently renovated and newly furnished, this lovely in-town cottage is close to all the amenities and charms of historic ...
From $745 per night (USD)
Expedia
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 $309 per night (USD)
Expedia
Relax or Play on the Choptank River!
Bedrooms:
2
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 $309 per night (USD)
Expedia
From $913 per night (USD)
VRBO
Luxurious waterfront home - Cèilidh
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Beautiful luxury waterfront home in historic downtown Oxford. A rare find with 2 piers, Beautiful luxury waterfront home ...
From $913 per night (USD)
VRBO
From $1500 per night (USD)
Expedia
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Talbot County STR License #ST-102-WEI Located just on the outskirts of St. Michaels, this fantastic family vacation com ...
From $1500 per night (USD)
Expedia
From $249 per night (USD)
VRBO
The Anchorage B&B - The Bounty
Bedrooms:
2
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 $1333 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 $1333 per night (USD)
Expedia
$Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n$
From $360 per night (USD)
VRBO
Waterfront, cozy cottage with private pool on 27 acres \n\n\n\n\n\n
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
FALL SPECIAL BOOK 3 NIGHTS AND GET A 1/2 BUSHEL OF CRABS FREE Located on a private 27 acre estate is nestled a mere 200 ...
From $360 per night (USD)
VRBO
From $685 per night (USD)
VRBO
Book a Week-Long Stay get a Crab Feast on Us!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Escape to this beautiful 4-bedroom waterfront home, offering stunning, wide-open views of the Chesapeake Bay. The primar ...
From $685 per night (USD)
VRBO
From $687 per night (USD)
VRBO
Rent 4 Nites, 5th Nite FREE! Waterfront, Dock, Hot Tub, Oxford Ferry.
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Another Luxury VIP Vacation Rental Property License # STRN-22-25 Stay at this comfortable property minutes from the qu ...
From $687 per night (USD)
VRBO
From $1633 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 $1633 per night (USD)
Expedia
From $1049 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin
Bedrooms:
6
Bathrooms:
5
Sleeps:
9
Eastern Shore Vacation Rentals presents The Water House. Beautifully appointed with artwork and antiques, The Water Hous ...
From $1049 per night (USD)
VRBO
From $770 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 $770 per night (USD)
Expedia
From $729 per night (USD)
VRBO
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 $729 per night (USD)
VRBO
From $549 per night (USD)
Expedia
Downtown Oxford | Charming | Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In-town cottage with loads of charm and easy walking to parks and restaurants Tucked away in the quaint, historic town o ...
From $549 per night (USD)
Expedia
From $774 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 $774 per night (USD)
VRBO
From $260 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 $260 per night (USD)
Expedia
$LUXURY COASTAL FARMHOUSE WATERFRONT W\/ HEATED POOL$
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 $835 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 $835 per night (USD)
Expedia
From $495 per night (USD)
VRBO
BOOK NOW FOR SPRING & SUMMER DATES.
Bedrooms:
3
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 $505 per night (USD)
Expedia
Downtown Oxford | Charming | Pet Friendly | Bikes
Bedrooms:
4
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 $505 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Bedrooms:
3
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 $672 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Dollhouse in Central Historic St Michaels
Bedrooms:
2
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 $299 per night (USD)
Expedia
From $846 per night (USD)
VRBO
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Bedrooms:
3
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 $846 per night (USD)
VRBO
From $1379 per night (USD)
Expedia
Baydream Believer - Eastern Shore MD Luxury Waterfront Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
BAYDREAM BELIEVER This home is a waterfront wonderland with plenty to do, from tubing and boating to fishing and crabbi ...
From $1379 per night (USD)
Expedia
$Waterfront Oyster Farmhouse Built 2018 with Pool\/Fence and Dock-23 private acres$
From $1126 per night (USD)
VRBO
Waterfront Oyster Farmhouse Built 2018 with Pool\/Fence and Dock-23 private acres
Bedrooms:
5
Bathrooms:
5
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 $1126 per night (USD)
VRBO
From $808 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 $808 per night (USD)
Expedia
From $358 per night (USD)
VRBO
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
The extraordinary fully restored historic John Bruff House, located on the Town park and harbor, has magnificent St. Mic ...
From $358 per night (USD)
VRBO
From $398 per night (USD)
VRBO
The heart of St Michaels awaits.
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
Basked in natural light, the open-plan interior boasts a chic coastal décor that exudes tranquility and sophistication. ...
From $398 per night (USD)
VRBO
From $1190 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
Bedrooms:
4
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 $1190 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
The recently restored historic Washington Melson House, located at 206 Locust St. is a 2 bedroom vacation cottage that i ...
From $336 per night (USD)
Expedia
From $507 per night (USD)
VRBO
Waterfront 3-Bedroom Cottage and Pet Friendly
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to tranquility at this beautiful 3-bedroom cottage, perfectly positioned on the waterfront to offer serene views ...
From $507 per night (USD)
VRBO
From $557 per night (USD)
Expedia
The Water's Edge Rental Cambridge, Md - sleeps 10, 4 bedrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to our newly renovated 1920s Waterfront bungalow, where there is something for everyone. Looking for a getaway ...
From $557 per night (USD)
Expedia
From $990 per night (USD)
VRBO
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks APRIL WINFEST
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Ingleton! EARLY CHECKIN AND LATECHECKOUT FOR APRIL AND MAY. Relax by the pool. Fish or crab or picnic at th ...
From $990 per night (USD)
VRBO
From $509 per night (USD)
Expedia
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 $509 per night (USD)
Expedia
From $638 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 $638 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Walk to Everything House
Bedrooms:
2
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 $358 per night (USD)
Expedia
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VRBO
Cottage downtown on a quiet street
Bedrooms:
2
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 ...
Click For Pricing
VRBO
From $2255 per night (USD)
Expedia
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 12 adults. Located on ...
From $2255 per night (USD)
Expedia
From $285 per night (USD)
VRBO
5 bedroom Bed and Breakfast 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 $285 per night (USD)
VRBO
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Expedia
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Location in Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Enjoy your own private condo-style Junior Suite, and suite cottage at Sandaway Suites & Beach in Oxford, MD. Please note ...
Click For Pricing
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 ...
Click For Pricing
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 ...
Click For Pricing
Expedia
From $558 per night (USD)
VRBO
Attractive Waterfront Home over looking Choptank River. Sleeps 5
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
This remolded waterfront home has a open floor plan for entertaining and comfortable living. The view of the river is f ...
From $558 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 $670 per night (USD)
VRBO
Waterfront Property, kayaks, private dock, near town
Bedrooms:
3
Bathrooms:
4
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 $670 per night (USD)
VRBO
From $266 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 $266 per night (USD)
Expedia
From $516 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 $516 per night (USD)
VRBO
From $1184 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 $1184 per night (USD)
Expedia
From $1944 per night (USD)
VRBO
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
TREMEZZO STAY - SPENCER CREEK CABIN Our properties are owned, managed, and hosted by us. We deliver personally hosted ...
From $1944 per night (USD)
VRBO
From $1038 per night (USD)
Expedia
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
FALL SPECIAL BOOK 3 NIGHTS AND GET A 1 BUSHEL OF CRABS FREE From the hosts that have maintained a five star ratings on ...
From $1038 per night (USD)
Expedia
$Choptank River Beach Home w\/ Pier in Cambridge!$
From $681 per night (USD)
VRBO
Choptank River Beach Home w\/ Pier in Cambridge!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Riverfront Location | In-Unit Washer & Dryer | Gas Grill for Group Cookouts Your next waterfront retreat awaits at thi ...
From $681 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Best rates of the season, book today!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Great 4 bedroom 2 bath home. Home offers first floor queen primary suite. 2 family rooms and a large eat in kitchen w ...
From $384 per night (USD)
VRBO

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