Talbot Area Rentals
- From $850 per night (USD)
VRBO
Minutes from Downtown Oxford and Easton | Pool | Private Dock | Pet Friendly | K
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This charming 4-bedroom, 4-bathroom historic shore house sits on 4+ acres with 450+ ft of waterfront. The free-flowing f ...
From $850 per night (USD)VRBO
- From $371 per night (USD)
Expedia
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 $371 per night (USD)Expedia
- From $1785 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 $1785 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
Waterfront Estate. **WALK TO ST. MICHAELS!**
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to Ship's Cove!! This three acre estate is your private oasis for the duration of your stay. Make some memories ...
From $1500 per night (USD)Expedia
- Click For Pricing
VRBO
Thorntonwood | an ESVR property
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License STRN-22-6 Thorntonwood offers a plethora of opportunities for indoor and outdoor fun! The hom ...
Click For PricingVRBO
- From $341 per night (USD)
Expedia
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The truly special and recently restored historic Thomas Blades House is centrally located in the Historic District of St ...
From $341 per night (USD)Expedia
- From $1499 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 $1499 per night (USD)VRBO
- Click For Pricing
Expedia
St. Michaels Area Cottage - Walk to Water & Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The 'Land of Pleasant Living' awaits your arrival at Blue Bird Cottage, a 2-bedroom, 2-bathroom Neavitt vacation rental ...
Click For PricingExpedia
- From $373 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 $373 per night (USD)VRBO
- From $2500 per night (USD)
Expedia
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 $2500 per night (USD)Expedia
- From $541 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 $541 per night (USD)VRBO
- From $561 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 $561 per night (USD)Expedia
- From $606 per night (USD)
VRBO
Minutes from Downtown Oxford and Easton | Pool | Private Dock | Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License# STRN-22-9 Judith's Garden is a delightful home located off the beaten path, yet close to the ...
From $606 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Minutes from Downtown Easton | Pool | Hot Tub | Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Cool waterfront contemporary with retro vibe Located on the serene banks of Skipton & Mill Creeks, this home offers plen ...
From $700 per night (USD)Expedia
- From $210 per night (USD)
VRBO
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 $210 per night (USD)VRBO
- From $1200 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 $1200 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Outdoor Dining
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A deep water pier with picturesque views make this a truly special spot for a weekend getaway or mini-vacation. With ple ...
From $325 per night (USD)VRBO
- From $769 per night (USD)
Expedia
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 $769 per night (USD)Expedia
- From $500 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 $500 per night (USD)VRBO
- From $400 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 $400 per night (USD)Expedia
- From $374 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 $374 per night (USD)VRBO
- From $592 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 $592 per night (USD)Expedia
- From $771 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 $771 per night (USD)VRBO
- From $272 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 $272 per night (USD)Expedia
- From $599 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 $599 per night (USD)VRBO
- From $1185 per night (USD)
Expedia
Large Waterfront Home 2 miles from town\nSpecial Rates!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Baydream Believer Formerly known for shipbuilding and oystering, St. Michaels, Maryland, calls itself “The Heart & Soul ...
From $1185 per night (USD)Expedia
- From $235 per night (USD)
VRBO
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 $235 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Hot Tub | Private Dock | Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sprawling Cottage with Hot Tub Under the Stars and Gorgeous Sunsets Over the Water A taste of paradise on the Chesapeake ...
From $351 per night (USD)Expedia
- From $891 per night (USD)
VRBO
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 $891 per night (USD)VRBO
- From $337 per night (USD)
Expedia
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 $337 per night (USD)Expedia
- From $317 per night (USD)
VRBO
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
- Bedrooms:
- 3
- 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 $317 per night (USD)VRBO
- From $338 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 $338 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $420 per night (USD)
Expedia
Downtown Oxford | Boat Slip | Bikes | Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bright and airy, 4-bedroom, 3-bathroom home features a first-floor bedroom with bath as well as an updated gourmet kitch ...
From $420 per night (USD)Expedia
- From $863 per night (USD)
VRBO
Waterfront Property, kayaks, private dock, near town
- Bedrooms:
- 3
- 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 $863 per night (USD)VRBO
- From $940 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 $940 per night (USD)Expedia
- From $1299 per night (USD)
VRBO
Waterfront St Michaels Vacation Rental w\/ Fire Pit
- Bedrooms:
- 4
- 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 ...
From $1299 per night (USD)VRBO
- From $562 per night (USD)
VRBO
Historic Elegance and Modern Luxury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This three bedroom, three bathroom cottage offers an exclusive escape, combining comfort and modern luxuries. I ...
From $562 per night (USD)VRBO
- From $1339 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 $1339 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $225 per night (USD)
VRBO
Perfect Waterview Cottage - St. Michaels Getaway
- Bedrooms:
- 2
- 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 $225 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Deep Neck Point is a very private luxury waterfront retreat able to comfortably accommodate up to 12 adults. Located on ...
From $1500 per night (USD)VRBO
- From $195 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 $195 per night (USD)VRBO
- Click For Pricing
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 PricingVRBO
- Click For Pricing
VRBO
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 PricingVRBO
- From $745 per night (USD)
Expedia
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Ingleton! Relax by the pool. Fish or crab or picnic at the end of the pier. Do all three. Go biking. Go ...
From $745 per night (USD)Expedia
- From $390 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 $390 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Waterfront Oyster Farmhouse Built 2018 with Pool\/Fence and Dock-23 private acres
- Bedrooms:
- 5
- 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 $900 per night (USD)VRBO
- From $418 per night (USD)
VRBO
BOOK NOW FOR FALL & WINTER 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 $418 per night (USD)VRBO
- From $1071 per night (USD)
VRBO
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels \/ Easton
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
5 Bedroom, 3.5 Bath, Pool, Dock Private Retreat. Welcome to Travelers Rest! A quiet and secluded neighborhood true to ...
From $1071 per night (USD)VRBO
- From $225 per night (USD)
VRBO
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 $225 per night (USD)VRBO
- From $204 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 $204 per night (USD)VRBO
- From $729 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 $729 per night (USD)VRBO
- From $1200 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 $1200 per night (USD)VRBO
- From $995 per night (USD)
VRBO
Tranquil Easton Waterfront Property (Pool, Tennis court, Hot Tub, Fireplace)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
4+ acres on Shipshead Creek off of St. Michaels Road. Fully furnished (2 king and 4 twin beds), pool, hot tub, deep wate ...
From $995 per night (USD)VRBO
- From $1299 per night (USD)
Expedia
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 $1299 per night (USD)Expedia
- From $895 per night (USD)
VRBO
Historic estate, where land and water meet .
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Combsberry where land and water meet. An historic estate situated on the northern headwaters of Island Creek. A ...
From $895 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Hurry, reserve your stay for \nSummer & Fall of 2024\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 $499 per night (USD)VRBO
- From $680 per night (USD)
VRBO
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
All persons thinking about making a booking, should consider adding travel cancellation insurance, prior to booking. Th ...
From $680 per night (USD)VRBO
- From $404 per night (USD)
VRBO
BOOKING FALL & WINTER-ACT NOW FOR BEST AVAILABILITY!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-217-HARG Within minutes of historic St Michaels this 4 BEDROOM waterfront home is located on Tilghman Island. A wat ...
From $404 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Jellyfish Cottage - 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 $375 per night (USD)VRBO
- From $558 per night (USD)
VRBO
Charming Waterfront Cottage Outside St. Michaels Close to the Oaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Contact us for other pricing options and special rates. Beautifully renovated one story home directly on the water. Gor ...
From $558 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $400 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 $400 per night (USD)VRBO
- From $650 per night (USD)
VRBO
🦆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 $650 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
SEPT SUMMERS & FREE BUSHEL OF CRABS W\/SEPT\/OCT BOOKING
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County MD License #STRN-23-16 - The Cove At St. Michaels is a magnificent 15.5 acre estate property with ingrou ...
From $1200 per night (USD)Expedia
- From $1479 per night (USD)
VRBO
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 $1479 per night (USD)VRBO
- From $330 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 $330 per night (USD)VRBO
- From $620 per night (USD)
VRBO
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
- Bedrooms:
- 4
- 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 $620 per night (USD)VRBO
- From $250 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 $250 per night (USD)VRBO
- From $805 per night (USD)
VRBO
Beautiful, 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 $805 per night (USD)VRBO
- From $210 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 $210 per night (USD)VRBO
- From $1119 per night (USD)
VRBO
Comfortable Relaxing Spacious & Fun! 6+ Acres Pool+Bay Waterfront by St Michaels
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
TALBOT COUNTY SHORT-TERM RENTAL LICENSE: ST-895-REH 2019 10 Person Maximum PEAK SEASON BOOKINGS ARE 7 DAY OR MORE BOOK ...
From $1119 per night (USD)VRBO
- From $575 per night (USD)
VRBO
WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY!
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
STRN-23-22 Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Easte ...
From $575 per night (USD)VRBO
- From $490 per night (USD)
VRBO
Waterfront Home with Magnificent Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
A converted barn house with updated finishes is the perfect spot for your vacation on the Eastern Shore of the Chesapeak ...
From $490 per night (USD)VRBO
- From $960 per night (USD)
VRBO
Historic Oxford Waterfront Estate
- Bedrooms:
- 6
- 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 $960 per night (USD)VRBO
- From $660 per night (USD)
VRBO
St. Michael's Premier In-Town Rental with heated pool - Pool opens 4\/12\/24
- 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 $660 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
License No. ST-575-PRO Summer 7 Night Minimum Deep water dock will accommodate a 52' yacht! Catch fresh fish and g ...
From $650 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Eastern Shore Getaway Near St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
PERFECT COUPLE'S GET AWAY OR WRiTERS RETREAT! Dogs welcome to enjoy the private waterfront getaway on sixteen acres with ...
From $300 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County License #ST-611-SMI Elegantly furnished and located in a prestigious estate area of Talbot County, Blue G ...
From $1200 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Eastern Shore Waterside Cottage Near St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A completely renovated (2023) cottage on private wooded lot in the quaint, water side, historic community of Neavitt MD. ...
From $297 per night (USD)VRBO
- From $900 per night (USD)
VRBO
A Waterfront Escape Like No Other
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: The Farm at Bald Eagle Point is the great escape! Our guests can settle in and never have to leave this exclusi ...
From $900 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Charming Cottage on Bolingbroke Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally Private, quiet water-front cottage with wood burning fireplace and exclusively private 60' Lap Pool(open mid-Apr ...
From $350 per night (USD)VRBO
- From $607 per night (USD)
Expedia
Short Drive to Downtown Easton and St. Michaels | Pool | Newly Renovated | Priva
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Eastern Shore Vacation Rentals presents Sky View. The impressive 4BR, 3.5BA Wye River Sanctuary waterfront estate is cre ...
From $607 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Quaint Tilghman Island home
- Bedrooms:
- 3
- 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 $275 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Warmth and Comfort Await
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Step into a thoughtfully curated space where coastal decor meets serene comfort. The open-concept living area i ...
From $295 per night (USD)VRBO
- From $383 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 $383 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Your “Happy Place”-Updated beautifully 3 story home on quiet island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
An amazing escape on the Chesapeake Bay. Explore Tilghman Island by bike or boat. Enjoy fresh seafood from the local se ...
From $350 per night (USD)Expedia
- From $882 per night (USD)
VRBO
Minutes from Downtown Easton and St. Michaels | Private Dock | Pool | Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Eastern Shore Vacation Rentals presents Family Tides. The impressive 4BR, 3.5BA waterfront along Irish Creek is designed ...
From $882 per night (USD)VRBO
- From $310 per night (USD)
Expedia
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 $310 per night (USD)Expedia
- From $232 per night (USD)
VRBO
Newly Renovated Guest House located in Oxford MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a delightful stay in a recently renovated, newly furnished guest cottage with water views in charming Oxford, Mary ...
From $232 per night (USD)VRBO
- From $650 per night (USD)
VRBO
EASTON Beautiful APT. 2bed2bathKitchinDining\/living room-walk to all places
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Downtown EASTON -Beautiful Mezzanine APARTMENT with cathedral celling's -2 bed 2bath- Kitchen Dining area large living r ...
From $650 per night (USD)VRBO
- From $231 per night (USD)
VRBO
Easton \/ St. Michaels Retreat
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
POOL OPEN 3/25/24 Relax with the whole family at this peaceful place to stay. Welcome to Travelers Rest! A quiet and sec ...
From $231 per night (USD)VRBO
- From $987 per night (USD)
Expedia
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 $987 per night (USD)Expedia
- From $348 per night (USD)
VRBO
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 $348 per night (USD)VRBO
- From $233 per night (USD)
Expedia
Spacious Trappe Getaway w\/ Outdoor Pool & Gazebo!
- Bedrooms:
- 3
- 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 $233 per night (USD)Expedia
- From $1070 per night (USD)
VRBO
Heated pool, sandy beach, pier, and playground set punch point apart!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
TREMEZZO STAY - PUNCH POINT Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury re ...
From $1070 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Discover Your Perfect Getaway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: We've put extra care into creating a welcoming atmosphere for you to relax and make the most of your time in th ...
From $325 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Luxurious Living with Stunning Sunset Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Sunsets Edge , a true waterfront retreat. . This three bedroom, 2.5 bathroom home offers a unique bl ...
From $700 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Close to Everything!Surrounded By Water! Dock and Pool. A VIP Vacation Property.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
STN-23-3 NEW MASTER BATH RENOVATION! At the end of the long, private driveway, you will find a lovely home situated on 2 ...
From $900 per night (USD)VRBO