Harris Creek Rentals
- From $350 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 $350 per night (USD)VRBO
- From $407 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 $407 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 $525 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 $525 per night (USD)Expedia
- From $371 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 $371 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- Click For Pricing
VRBO
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 PricingVRBO
- 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 $700 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 $700 per night (USD)VRBO
- From $1000 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 $1000 per night (USD)Expedia
- 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 $1135 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 $1135 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 $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 $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 $2938 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 $2938 per night (USD)Expedia
- 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 $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 $1650 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 $1650 per night (USD)VRBO
- From $825 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 $825 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 $399 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 $399 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 $297 per night (USD)
Expedia
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)Expedia
- From $950 per night (USD)
VRBO
A Waterfront Escape Like No Other
- Bedrooms:
- 5
- 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 $950 per night (USD)VRBO
- From $328 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 $328 per night (USD)Expedia
- From $1032 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 $1032 per night (USD)VRBO
- From $685 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides ...
From $685 per night (USD)Expedia
- From $290 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 $290 per night (USD)VRBO
- From $775 per night (USD)
VRBO
Grandview - Main House
- Bedrooms:
- 3
- 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 $775 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Unwind at this Waterfront Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: This beautiful home is minutes from historic St Michaels. Enjoy your morning coffee on the covered deck. Days c ...
From $625 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Landon Cottage is in the waterfront village of Sherwood on Eastern Shore of MD
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The village of Sherwood is located on Harris Creek. The cottage, at 21902 Sherwood Landing Rd., is a perfect place to r ...
From $150 per night (USD)VRBO
- From $667 per night (USD)
VRBO
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County STR License STN-23-31 Welcome to Gratitude Farm, a newly renovated 1890s farmhouse offering the ultimate ...
From $667 per night (USD)VRBO
- From $317 per night (USD)
Expedia
Minutes from Downtown St. Michaels and Tilghman | Newly Renovated | Kayaks | Cha
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eastern Shore Vacation Rentals presents Banyan Cottage. This impressive and simply idyllic 2BR/2BA vacation cottage is t ...
From $317 per night (USD)Expedia
- From $538 per night (USD)
VRBO
NEW LISTING! Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This met ...
From $538 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Enjoy the beautoful reflections of sunsets and the golden leaves on the water!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
ST-23-30 Just minutes from St Michaels this contemporary home is the perfect waterfront retreat. Offered for the f ...
From $850 per night (USD)VRBO
- From $1395 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 $1395 per night (USD)VRBO
- From $1348 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 $1348 per night (USD)Expedia
- From $757 per night (USD)
VRBO
Persimmon Point Waterfront, Dock & Heated Pool Casual Comfortable Fun
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County ST Rental License: ST-785-WAT New 2022 Listing! 8 Persons Maximum PEAK SEASON BOOKINGS ARE 7 DAY OR MORE ...
From $757 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County STR License #ST-643-DER Originally a waterman's cottage, Neavitt Cottage has been tastefully updated (sup ...
From $425 per night (USD)Expedia
- From $795 per night (USD)
VRBO
Waterfront - NEW BOOK 2024 AND RECEIVE 100 Gift CERT FOR SEAFOOD FROM \nLANDING
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Talbot County MD License #STRN-22-41 Water front home nestled in quaint village of Bozman with dock/pier for fishing, ...
From $795 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Fabulous SUMMER rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This newly built cottage is located in the quaint waterman's community of Tilghman Island. The perfect spot to ...
From $215 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Book a week in July\/August & steamed crabs on us!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: As you head down the tree lined drive you will instantly know you are about to be somewhere special. A perfect ...
From $800 per night (USD)VRBO
- From $700 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 $700 per night (USD)VRBO
- From $977 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 $977 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
LUXURY COASTAL FARMHOUSE WATERFRONT W\/ HEATED POOL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
STRN-22-40 Come slip away and enjoy Perry Point—a custom built nautical farmhouse that provides the best combination of ...
From $1000 per night (USD)VRBO