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From $351 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 $351 per night (USD)
VRBO
From $2315 per night (USD)
Expedia
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 $2315 per night (USD)
Expedia
From $363 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 $363 per night (USD)
VRBO
From $1347 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 $1347 per night (USD)
Expedia
From $415 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 $415 per night (USD)
VRBO
From $753 per night (USD)
Expedia
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Pool | 8.6 Acre
Bedrooms:
3
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)
Expedia
From $708 per night (USD)
VRBO
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of hist ...
From $708 per night (USD)
VRBO
From $307 per night (USD)
Expedia
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)
Expedia
From $1863 per night (USD)
VRBO
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
Bedrooms:
4
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 $1863 per night (USD)
VRBO
From $1069 per night (USD)
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 ...
From $1069 per night (USD)
Expedia
From $665 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 $665 per night (USD)
VRBO
From $774 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 $774 per night (USD)
Expedia
From $534 per night (USD)
VRBO
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 $534 per night (USD)
VRBO
From $712 per night (USD)
Expedia
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 $712 per night (USD)
Expedia
From $790 per night (USD)
VRBO
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 $790 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 $789 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 $789 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
From $525 per night (USD)
VRBO
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 $525 per night (USD)
VRBO
From $728 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 $728 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 $331 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 $331 per night (USD)
Expedia
From $358 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 $358 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 ...
Click For Pricing
Expedia
From $731 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 $731 per night (USD)
VRBO
From $1217 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 $1217 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront St Michaels Vacation Rental w/ Fire Pit
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Wake up on the water with a stay at this stylish 3-bedroom, 3.5-bath, St Michaels vacation rental! Relax, recharge, and ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Cozy 3 bedroom historic cottgage in Oxford, MD avialable Aug 2024
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 bedroom cottage/ 2 1/2 baths. Kitchen, living/ dining area. outdoor shower after coming from the beach 1 block away.Ou ...
Click For Pricing
Expedia
From $682 per night (USD)
VRBO
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 $682 per night (USD)
VRBO
From $386 per night (USD)
Expedia
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 $386 per night (USD)
Expedia
From $860 per night (USD)
VRBO
Family & Friends Paradise – Pool, BBQ, & More!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Gather your favorite people and make yourself at home in this bright, cheerful 3-bedroom retreat—just minutes f ...
From $860 per night (USD)
VRBO
$Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n$
From $237 per night (USD)
Expedia
Cozy getaway! Centrally located between St. Michaels and Tilghman Island\n\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Unwind in Wittman at this welcoming house. With 3 cozy bedrooms including a queen bed, full bed, and bunk bed, guests wi ...
From $237 per night (USD)
Expedia
From $1020 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 $1020 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 $626 per night (USD)
VRBO
Time Stands Still At the Dock.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Minutes from St Michaels, this peaceful retreat will have guests never wanting to leave. Panoramic views of the ...
From $626 per night (USD)
VRBO
Click For Pricing
Expedia
Charming 1-bedroom cottage in downtown Saint Michaels
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay comfortably in Saint Michaels at this 1-bedroom cottage. Nestled in a beautiful and peaceful setting, this brillian ...
Click For Pricing
Expedia
From $1359 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Take control of your next vacation. Escape to your dream waterfront vacation at this extraordinary 5-bedroom estate on ...
From $1359 per night (USD)
VRBO
From $689 per night (USD)
Expedia
Charming, Waterfront 2-bedroom house Royal Oak
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your cozy getaway awaits in Royal Oak at this brilliant house. With 2 bedrooms guests can unwind in comfort. The proper ...
From $689 per night (USD)
Expedia
From $1018 per night (USD)
VRBO
Downtown Oxford | Private Beach | Private Pool | Luxury
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxury awaits at The Beach House, a stunning 4-bedroom, 4.5-bathroom vacation extravaganza in the vibrant Oxford neighbo ...
From $1018 per night (USD)
VRBO
From $1229 per night (USD)
Expedia
Waterfront Farmhouse | Pool, Dock, Pets Welcome
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Imagine waking up to the gentle lapping of water on a quiet inlet, just a short drive from the charming streets ...
From $1229 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Cottage #5 White Swan At Water with Deck
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $315 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Cottage #8 Herons Nest Lg 2 rooms Under Main House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our beautiful waterfront property, open for guests from March 25th to November 1st. We have a minimum stay of ...
From $371 per night (USD)
Expedia
From $744 per night (USD)
VRBO
Midweek Deals Await – Reserve Your Stay Today!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Acorn Cottage sits on a private cove at the end of Oak Creek offering an open-concept living space that is bright, airy, ...
From $744 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Pet-Friendly Cottage – Ideal for Summer Getaways!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Fishin Frank's Cottage on Tilghman Island Tucked away in the charming Watermans community of Tilghm ...
From $428 per night (USD)
Expedia
From $1236 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 $1236 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 ...
Click For Pricing
Expedia
From $2552 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 $2552 per night (USD)
VRBO
From $285 per night (USD)
Expedia
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)
Expedia
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 FOR APRIL AND MAY. Relax by the pool. Fish or crab or picnic at th ...
From $1173 per night (USD)
VRBO
From $434 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 $434 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Easter Weekend open 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 $457 per night (USD)
VRBO
From $248 per night (USD)
Expedia
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)
Expedia
From $805 per night (USD)
VRBO
3BR Home: Serene Escape, Pet-Friendly, Fireplace
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Step into a realm of sophistication, where high-end furnishings meet bespoke décor, creating a seamless fusion of modern ...
From $805 per night (USD)
VRBO
From $1064 per night (USD)
Expedia
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 $1064 per night (USD)
Expedia
From $500 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 $500 per night (USD)
VRBO
From $249 per night (USD)
Expedia
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)
Expedia
From $963 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 $963 per night (USD)
VRBO
From $1325 per night (USD)
Expedia
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)
Expedia
$Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30$
From $611 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 $611 per night (USD)
VRBO
From $1540 per night (USD)
Expedia
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 $1540 per night (USD)
Expedia
From $1154 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 $1154 per night (USD)
VRBO
From $555 per night (USD)
Expedia
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 $555 per night (USD)
Expedia
From $1778 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 $1778 per night (USD)
VRBO
From $981 per night (USD)
Expedia
Pet-Friendly Stay with Pool – Relax & Unwind!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Summary: Discover Combsberry: A Historic Oasis. Nestled on 30 acres of picturesque countryside, Combsberry is a beautif ...
From $981 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 $512 per night (USD)
Expedia
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 $512 per night (USD)
Expedia
From $296 per night (USD)
VRBO
The B&B of Anchorage - Skipjack
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 $296 per night (USD)
VRBO
From $1398 per night (USD)
Expedia
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 Discover ...
From $1398 per night (USD)
Expedia
From $682 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 $682 per night (USD)
VRBO
From $1088 per night (USD)
Expedia
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 $1088 per night (USD)
Expedia
From $794 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 $794 per night (USD)
VRBO
From $1017 per night (USD)
Expedia
Waterfront, Pool, Dock, Hot Tub.Stunning Views! 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 $1017 per night (USD)
Expedia
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 $544 per night (USD)
Expedia
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 $544 per night (USD)
Expedia
From $913 per night (USD)
VRBO
Tuckaway Cove. Openings in August and the fall. Brand new kitchen!
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)
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 $1546 per night (USD)
VRBO
Classic Eastern Shore Waterfront Manor House - ST-936
Bedrooms:
4
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 $1546 per night (USD)
VRBO
From $403 per night (USD)
Expedia
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 $403 per night (USD)
Expedia
From $701 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 $701 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 $903 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 $903 per night (USD)
VRBO
From $691 per night (USD)
Expedia
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Downtown EASTON -Beautiful Mezzanine APARTMENT with cathedral celling's -3 bed 3bath- Kitchen Dining area large living r ...
From $691 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This newly renovated 3BR, 3BA Sherwood vacation home is designed with your comfort in mind. The free-flowing floor plan ...
From $491 per night (USD)
VRBO
From $254 per night (USD)
Expedia
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 $254 per night (USD)
Expedia
From $1668 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 $1668 per night (USD)
VRBO
From $368 per night (USD)
Expedia
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 $368 per night (USD)
Expedia
From $1209 per night (USD)
VRBO
Time Stands Still, While Memories Are Made.
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: The Farm at Bald Eagle Point is the great escape! Our guests can settle in and never have to leave this exclusi ...
From $1209 per night (USD)
VRBO
From $1228 per night (USD)
Expedia
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Vacation With No Limits! The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is created by a sprawling inte ...
From $1228 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Quaint Tilghman Island home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Vacation home minutes from St Michaels. Tucked away on a quiet neighborhood street is the Wandering Loon. A pe ...
From $376 per night (USD)
VRBO
From $397 per night (USD)
Expedia
4-Bedroom Retreat: Modern, Pet-Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Heart of the Island & Pet Friendly Retreat on Tilghman Island! Step into a thoughtfully curated space where coa ...
From $397 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Eastern Shore Vacation Rentals presents Oyster Cottage. Just a 10-minute drive from historic St. Michaels and Tilghman I ...
From $624 per night (USD)
VRBO
Click For Pricing
Expedia
Minutes from Downtown Easton and St. Michaels | Private Dock | Pool | Kayaks
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Sha La La La … Fun For Everyone! The impressive 5BR, 3BA, 2 half BA waterfront along Irish Creek is designed with relax ...
Click For Pricing
Expedia
From $1358 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 $1358 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Brand New Pool and Hot Tub Coming June 2024 This 2-bedroom, 2-bathroom waterfront getaway features a character-filled i ...
From $546 per night (USD)
Expedia
From $400 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 $400 per night (USD)
VRBO
From $1236 per night (USD)
Expedia
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 $1236 per night (USD)
Expedia
From $1427 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to your dream retreat, nestled in a serene cove that feels like a page from a fairytale. This enchanting waterfr ...
From $1427 per night (USD)
VRBO
From $1092 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
A breathtaking waterfront estate that seamlessly combines luxury and nature. Welcome to Miles End, a breathtaking water ...
From $1092 per night (USD)
Expedia
From $972 per night (USD)
VRBO
Stunning Chesapeake Waterfront Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. ...
From $972 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

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