Homes for Rent near St. Michaels Middle/High School

RARE Chesapeake Bay beach side rental with 2 BDR, 2BTH guest house on 2+ Acres. You can enjoy the salt air and fabulous sunsets in any season! Furnished and ready for occupancy.

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

Public Open House Saturday 8/16 2-4pm. Discount given if move-in date is in August 2025.Welcome to Presquile Haven — A Historic Waterfront Gem in EastonExperience the unmatched charm of this beautifully restored, fully furnished retreat at 26692 Presquile Rd., Easton, MD. Nestled along the serene East Wye River, Presquile Haven offers breathtaking water views, a brand-new dock,

Nico Garcia EXP Realty, LLC

Gorgeous waterfront Provencal style home sitting on 5 acres on the Miles River with pool and pier.If you are looking for a great spot to rent for 4-9 months this would be a great option; Welcome to Holly House! This extremely well-constructed French provincial style one story brick residence proudly sits on a 5 acre spectacular Miles River waterfront lot. Enjoy broad water-views and

Tom Williams TTR Sotheby's International Realty

Freshly painted and move-in ready, this charming rental offers easy access to both Easton and St. Michaels. Enjoy peaceful outdoor living with brand new decking, a spacious yard, and a quiet setting. Well-maintained and thoughtfully updated, this home is a perfect blend of comfort and convenience.

Hayden Smith Benson & Mangold, LLC

Great location!! Walk to town, trail, schools and pool! Huge primary suite with vaulted ceilings and sitting room, breezy front porch and rear deck. 3 additional bedrooms, living room, separate dining room, family room with fireplace, 2 zone heat pumps, and one car attached garage. Lawn maintenance included !! pets on case by case. Credit report and references required.

Drew Buniski Benson & Mangold, LLC

Beautiful 2 bedroom townhouse located just outside St Michaels. Two levels, this home has two en suite bedrooms on the first floor, and an open concept living room/kitchen on the second floor. Half bath upstairs, along with a wood burning fire place and private outdoor balcony. This is a waterfront neighborhood that provides access to a community park right on the Miles River. Looking for a one

Jimmy Higgins Benson & Mangold, LLC

Welcome to this beautiful, spacious 5-bedroom, 3 1/2-bathroom single-family home located in the sought-after Tilghman on Chesapeake community. This property offers the perfect blend of modern comfort and serene island living, featuring an open-concept floor plan with plenty of natural light and elegant finishes. Each bedroom offers ample space and comfort with the Primary Suite offering 2

Becky Wibberley Coldwell Banker Realty

Water access community. Comes with club house and pool privileges. House can be partially furnished if needed. 3 beds, 2 full baths with an oversized living room, kitchen area, dining area, laundry room, screened in rear porch to enjoy the evening sunsets of Eastern Bay.

Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

5 bedroom fully restored waterfront farmhouse with dock. Tenant is responsible for yard maintenance. Total privacy on this waterfront farm. Gated security. Credit application and references required. Must have minimum 650 credit score.

Schuyler Benson Benson & Mangold, LLC

3 bedroom waterfront country farmhouse with private dock on Balls Creek. 1 bedroom down and 2 bedrooms up. Country kitchen and large family room with fireplace. Gated entry. Credit application - minimum 650 credit score and references required.

Schuyler Benson Benson & Mangold, LLC