Harris Creek Rentals
From $763 per night (USD)VRBO
Minutes from Downtown St. Michaels | Private Dock | Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Easy, One-Level Living Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play ...
From $763 per night (USD)VRBO
From $329 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 $329 per night (USD)Expedia
From $296 per night (USD)VRBO
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 $296 per night (USD)VRBO
From $723 per night (USD)Expedia
Pet-Friendly 3 bedroom with a Pool, Hot Tub & Near St. Michaels
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Your perfect fall Chesapeake getaway awaits! Just minutes from the charming harbor town of St. Michaels, this 3 ...
From $723 per night (USD)Expedia
From $1119 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 $1119 per night (USD)VRBO
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 $931 per night (USD)VRBO
Private Retreat with HUGE Water Views!!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Wonderful large family home on Harris Creek. With 6 bedrooms and 3 full bathrooms (including master bedroom suite), th ...
From $931 per night (USD)VRBO
From $1534 per night (USD)Expedia
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 12
TREMEZZO STAY - CHEASAPEAKE MANSION Our properties are owned, managed, and hosted by us. We deliver personally hosted l ...
From $1534 per night (USD)Expedia
From $584 per night (USD)VRBO
Hurry, reserve your stay for \nSummer & Fall of 2025\nSTR #22-30
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Offering a HOMEY rental on the gorgeous Chesapeake Bay - Leadenham Creek, Bozman, MD. The Gnome Home is nestled on 3 1 ...
From $584 per night (USD)VRBO
From $1179 per night (USD)VRBO
Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings **IMPORTA ...
From $1179 per night (USD)VRBO
From $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 $256 per night (USD)Expedia
Relaxing Waterfront Cottage Near St Michaels, Maryland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Eastern Shore two bedroom cottage with dock on a quiet creek of the Chesapeake Bay in Wittman, Maryland. Surrounded by ...
From $256 per night (USD)Expedia
From $1062 per night (USD)VRBO
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and absorb the beauty of living on the water at our 23 acre waterfront property on Harris Creek, in between histor ...
From $1062 per night (USD)VRBO
From $407 per night (USD)Expedia
Stunning views at WATERFRONT St Michaels area historic home, dog friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Full renovations completed in 2016 on this historic home. Sleeps four (1 King, 1 Queen, 1 Twin). Kick back, relax and e ...
From $407 per night (USD)Expedia
From $248 per night (USD)VRBO
Perfect Waterview Cottage - St. Michaels Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipwright Cottage is a fully-renovated idyllic getaway located in the Bay Hundred area of the Chesapeake Bay just 8 mil ...
From $248 per night (USD)VRBO
From $324 per night (USD)VRBO
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 $324 per night (USD)VRBO
From $956 per night (USD)VRBO
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Discover the ultimate Eastern Shore escape at The Farm at Bald Eagle Point—a private 6-bedroom waterfront estat ...
From $956 per night (USD)VRBO
From $1177 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 $1177 per night (USD)Expedia
From $366 per night (USD)VRBO
Duck Cove Waterfront Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR License - STRN-24-52 Come enjoy our charming, fully updated and renovated waterfront cottage located in the Eastern ...
From $366 per night (USD)VRBO
From $194 per night (USD)Expedia
Charming 3 Bedroom Cottage – 6 Miles to St. Michaels
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Pot Pie Cottage — your charming, well-priced escape just minutes from the historic town of St. Micha ...
From $194 per night (USD)Expedia
From $301 per night (USD)VRBO
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for an Eastern Shore waterfront retreat that's perfect for a romantic long weekend, a family vacation with the k ...
From $301 per night (USD)VRBO
From $626 per night (USD)VRBO
Grandview - Main House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
GRANDVIEW, which was once known as Grandview at Pleasure Point, is a private estate located on 5¼ acres of Maryland’s f ...
From $626 per night (USD)VRBO
From $1077 per night (USD)VRBO
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
- Bedrooms:
- 4
- 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 $1077 per night (USD)VRBO
From $1708 per night (USD)Expedia
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 12
Looking to getaway, relax and recharge? This newly renovated coastal 7-bedroom, 6-bathroom waterfront getaway with a sp ...
From $1708 per night (USD)Expedia
From $1011 per night (USD)VRBO
Waterfront Paradise with Private Pool and Dock minutes from St Michaels
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 12
Duck Duck Goose – Tag, you’re it! Escape to this extraordinary 6-bedroom, 7-bathroom waterfront retreat, where a class ...
From $1011 per night (USD)VRBO
From $240 per night (USD)VRBO
Charming 1-bedroom cottage on the water, minutes from St Michaels MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
King Size Comfort. The ambience of each cottage is one of relaxed comfort. Fashionable cottage décor is enhanced with co ...
From $240 per night (USD)VRBO
From $925 per night (USD)VRBO
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Talbot County MD License #STN-24-6 Water front home nestled in quaint village of Bozman with dock/pier for fishing, cr ...
From $925 per night (USD)VRBO
From $805 per night (USD)VRBO
Secluded Waterfront Property on 3 acres with swimming pool and dock.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Open floor plan home with ample views of the Leadenham Creek. Salt water swimming pool overlooks 220 feet of shoreline ...
From $805 per night (USD)VRBO
From $907 per night (USD)VRBO
Beautiful Large 3 Bdrm Luxury suites with outdoor pool & spa, close walk to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Talbot County Short-Term Rental License STN-23-2 Villa estates ...
From $907 per night (USD)VRBO