$5,000 5 Beds ⋅ 5 Baths Executive Water Front fully furnished short term rental for Sept or Oct or both that includes the main house (5700+ sqft). All utilities & landscaping included (worth $1100+ a month). Looking for a late summer or short term rental, having a house built or just need an amazing 1 or 2 month rental for your family? Situated in a serene setting with the beauty of nature all around you, you will fall in love with this place. This exquisite home will take your breath away with a super master bedroom & bathroom on the 1st floor. Entertain and enjoy meals in the gourmet kitchen with separate freezer and refrigerator, granite counters, separate lounge area, all with waterfront views. Sit by the several fireplaces or play the piano as you watch nature and sunrises everyday. Use of owners kayaks a plus. This amazing home is fully & beautifully furnished. Enjoy the great location close to beaches, boat ramps, hospitals, shopping, doctors, restaurants and parks. 2620 Love Point Rd, Stevensville Listing courtesy of Taylor Properties. Contact:
$1,350 1 Beds ⋅ 1 Baths Rare opportunity to rent a truly one-of-a-kind, fully furnished all utilities paid solar passive home! Nestled on approximately a ¼-acre lot, this unique home also includes use (with permission by owner) of the adjacent lot, giving you nearly half an acre to enjoy. Designed with sustainability and comfort in mind, the home features 12-inch-thick walls with natural insulation and clay plaster to help regulate humidity year-round. The 6-inch-thick earthen floor is heated during the winter months, creating a cozy and consistent indoor temperature. A charming loft, accessed only by an alternating-tread staircase, adds character and makes the most of the home's efficient layout. Outside, you'll find a spacious screened porch and an adjoining patio—perfect for relaxing with your morning coffee or entertaining guests. A covered concrete parking area provides space for a small boat and trailer or a vehicle; A full driveway is also available to you. Find some security knowing all utilities are paid by the owner however, if tenant wishes to add additional utilities (more devices to internet service, or does not wish to take care of garden beds) those additions will be paid by tenant to owner. The lawn, excluding the garden beds are currently taken care of by a trusted landscaper. Nature lovers will appreciate the nearby walking trail, easily accessible from the property, which follows a small creek and leads to playgrounds, local restaurants, and the Centreville Wharf. Enjoy the peace and privacy of this home while remaining just a half mile from downtown Queen Anne, where you'll find restaurants, shopping, banks, a laundromat, and other everyday conveniences. Schedule a tour, come take a look, and don't miss this opportunity to rent such a unique home! 309 Windsor Ave, Centreville Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:
$3,900 4 Beds ⋅ 3 Baths Ever thought about living on the water but we're ready to commit? Well, here's your chance to live the waterfront life without the hassles of ownership. Beautifully remodeled home located on the picturesque Wye River. Boat to St. Michael's, the Kent Narrows all less than 30 minutes. The location has it all with a little country store a 2 min walk from the house, with everything you need from Homemade pizza, fill up your gas tank, buy a bottle of wine or just that one little item you forgot at the store. With 4 bedrooms, 2 full baths one ensuite and half bath in the hall. But wait how about a new gourmet kitchen to serve up all those meals. There's a great screened in porch off the kitchen ready to enjoy morning coffee of evening cocktails on, all while taking in the beauty of the Wye River. 109 Yewell Rd, Queenstown Listing courtesy of Rosendale Realty. Contact: 4107580333
$1,650 2 Beds ⋅ 1 Baths 446 Railroad Ave, Centreville Listing courtesy of CR Realty. Contact: 4104900460
$3,500 4 Beds ⋅ 4 Baths Luxury rentals rarely become available. This stunning end unit townhome offering 4 bedrooms, 3.5 bathrooms, and an impressive list of high end upgrades is available in sought after Ellendale Community. Filled with natural light, the open floor plan features hardwood floors, custom plantation shutters, elegant trim, and a built-in Bose surround sound system. The gourmet kitchen is equipped with stainless steel appliances, 42" soft close maple cabinetry, under cabinet & pendant lighting and stunning custom backsplash! Escape to the spacious primary suite with a tray ceiling and spa-like bath or unwind on the composite deck overlooking spectacular sunset views with a nice breeze off the bay. Remodeled bathrooms, LED lighting throughout, central vacuum and an oversized 2 car garage with custom storage. Located just minutes from the Bay Bridge, you will also enjoy resort style community amenities including a pool, clubhouse, fishing pier, boat storage, and walking trails... come enjoy the Eastern Shore lifestyle and live like you're on vacation all the time!! 118 Amanda Frances Ln, Stevensville Listing courtesy of RE/MAX Executive. Contact: 4432741900
$2,250 3 Beds ⋅ 1 Baths Welcome to 116 Walnut St. in the desirable Centreville Heights community! This well-maintained 3-bedroom home offers the best of both worlds—all the conveniences of in-town living while backing to open farm fields, providing beautiful views, added privacy, and a peaceful setting. Inside, you'll find beautiful hardwood floors, central air conditioning, and an energy-efficient tankless water heater. The spacious second floor has previously been used as a fourth bedroom, making it a great option for a guest room, home office, or additional living space. Step outside to the private side porch and enjoy your morning coffee or evening sunsets overlooking the surrounding farmland. The home also features a full unfinished basement, providing plenty of storage space. Conveniently located just minutes from downtown Centreville's shops, restaurants, parks, and schools, this home combines small-town convenience with the tranquility of a country backdrop. Available for $2,250 per month. Don't miss this rare rental opportunity—contact us today for additional information or to schedule your private tour. 116 Walnut St, Centreville Listing courtesy of CR Realty. Contact: 4104900460
$1,850 2 Beds ⋅ 1 Baths Completely renovated and move-in ready! This beautifully updated 2-bedroom, 1-bath home offers the perfect blend of modern upgrades and country charm in a convenient Grasonville location. Everything has been redone, including a new HVAC system, energy-efficient windows, fresh paint throughout, refinished hardwood floors, and a brand-new kitchen featuring new appliances. The bright, open living space is filled with natural light, while the inviting front porch provides the perfect spot to relax and enjoy the peaceful surroundings. The spacious yard offers plenty of room to enjoy the outdoors, with ample parking and easy access to Route 50, the Bay Bridge, shopping, dining, and local marinas. If you're looking for a clean, updated rental that's truly move-in ready, this home is a must-see. 600 Perrys Corner Rd, Grasonville Listing courtesy of CR Realty. Contact: 4104900460
$2,400 3 Beds ⋅ 1 Baths Cutest little rancher in the cutest little town! Welcome to Queenstown! Walk to the bank, post office, restaurant, waterfront overlook or even the GOLF COURSE! Quaint smalltown living at its finest! Brand new composite deck boards and vinyl rails. Brand new paver walkway and steps being completed. Updated kitchen!!! Newer cabinets! Newer quartz countertops! Newer appliances! Newer LVP flooring! Newer fence! Nice corner lot with water views! Hardwood and ceramic floors. Easy commute on and off of 301 to Annapolis, Easton, or wherever! 6808 Main St, Queenstown Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$2,750 3 Beds ⋅ 3 Baths 3 bedroom 2.5 bathrooms, all on one level. with newer carpet in bedrooms. In excellent condition. Upgraded kitchen with stainless steel appliances. New LVP flooring in all common areas. Large back yard with patio and firepit. Deck and shed. Hot tub to be used at tenants' own risk and expense. All this in the Cloverfield's neighborhood with community pool and beach area. Close to the Bay bridge and all local shopping and restaurants. Pets welcome case by case. Wood stove for show only. 908 May Ln, Stevensville Listing courtesy of Maryland Residential Management Co. Contact: (410) 451-3300
$4,000 3 Beds ⋅ 3 Baths This is What You Have Been Looking For + More! You'll love this Gorgeous 2600 sf Condo in Four Seasons @ Kent Island, a Premiere 55+ Community! This is a rare and quality offering of this modern and bright 2nd Floor end unit condo in a resort quality, waterfront community. This is the largest condo model built here by K.Hovnanian called The Severn with 3 Bedrooms and 2.5 Baths. It is being offered unfurnished with an approximate move in date of 9/15/26. It features a secure Lobby entrance in an Elevator Building with separate Garage + Private Driveway and a bonus conditioned, lobby-level walk-in storage closet. This is an upscale rental for those with discerning taste desiring state of the art features and lively community amenities and events. The interior has luxury vinyl plank flooring throughout with ceramic tile flooring in the bathrooms, modern kitchen with white shaker 42" cabinets, quartz counters, propane gas cooking and stainless-steel appliances. It has an incredible amount of storage with ample walk-in closets and built-in bookcases. The Balcony has room to relax and will accommodate a full-sized table and chairs with views of nature and glimpses of water views. Situated on the Chester River you will enjoy expansive community coastal water views and an abundance of community amenities that are included in your monthly rent. These include use of the 20,000 sf community clubhouse known as The Chester House which is where the fun begins! With an on-site activities director in charge there are any number of activities to choose from to include interesting lectures, field trips and a host of clubs to participate in like book clubs, cooking clubs and Mah Jongg! You will enjoy a sparkling outdoor infinity pool during the summer and a wonderful heated indoor pool & jacuzzi during the winter, a state-of-the-art gym, billiards room and poker room, dance and yoga exercise room, library, and lovely community kitchen and entertaining rooms + Ballroom for events. There is a tiki bar, outdoor furniture to relax in the shade and a section of Adirondack chairs out in the open space facing an amphitheater where live music events are hosted. And if that isn't enough there is a Fishing Pier, Tennis and Pickle Ball courts, Dog Park and Playground for the visiting grandkids. You'll run out of time before you run out of fun! This unit will also consider transitioning into a purchase so if you get here and love it, you can buy it! Owner seeking qualified renter - ideal candidate would be a non-smoker with no pets however a dog would be considered. Cats are not considered. Applicants must meet community age restricted guideline of 55+. Contact helpful Landlord Agent for more info and your private tour today! 190 Harrier Way Unit #24, Chester Listing courtesy of RE/MAX Leading Edge. Contact:
$2,800 1 Beds ⋅ 1 Baths Looking for a quite place on the Wye river, with pier, boat slip, giant pool, hot tub, kayaking, fishing, crabing, hunting, bird watching, two beaches, raft for floating, spectacular sunsets this is it. A first floor one bedroom apartment being remodeled with full kitchen, open space living room, dining, bedroom. Interior pictures uploaded when complete. 1140 Cheston Ln, Queenstown Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$3,500 3 Beds ⋅ 2 Baths 1035 Chester River Dr, Grasonville Listing courtesy of Wilson Realty & Staging LLC. Contact: 4103042250
$4,300 4 Beds ⋅ 3 Baths From the moment you arrive, you'll feel right at home. Relax on the expansive front porch and enjoy the peaceful natural surroundings, including serene views of the Corsica River. Inside, water views continue to enhance the home's timeless appeal. Welcome to 119 Watson Rd. Offered fully furnished, this exceptional home provides a rare opportunity to enjoy the character of a historic property with the comfort and convenience of modern living. Ideally located in the Historic Wharf district, just steps from Centreville Landing, you will have easy access to a public boat ramp, kayak launch, and nearby playground for endless outdoor recreation. Built in 1880, this charming Colonial farmhouse has been thoughtfully renovated to preserve its historic character while incorporating modern updates. Gorgeous hardwood floors span both levels, while a striking double-sided brick fireplace serves as a beautiful focal point, elegantly defining the living and dining areas. The gourmet kitchen features quartz countertops, soft-close cabinetry, and opens seamlessly to the family room, creating an inviting space for everyday living. Sliding doors lead to a brick patio and private backyard, perfect for entertaining or simply enjoying the outdoors. The main level offers two bedrooms and a versatile bonus space, ideal for a home office with inspiring water views. The primary suite is a true retreat, featuring vaulted ceilings, exposed beams, and a private deck overlooking the water. A spacious dressing room and spa-inspired bath with a freestanding soaking tub and oversized glass walk-in shower provide a luxurious escape. The upper level also includes an additional family room, a full bath, a dedicated laundry room, and a fourth bedroom with charming architectural details. 119 Watson Rd, Centreville Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
$2,800 2 Beds ⋅ 3 Baths Come see this freshly renovated waterview unit in Queens Landing! More photos to come, kitchen and bathrooms are being renovated. Enjoy Chester River views from all angles! The spacious first floor with a half bath has plenty of room for living, dining and whatever else you desire. The upper level features two bedrooms each with their own waterview balcony and full bathroom (one in the hall and one en-suite. Washer/dryer on 2nd level. The second bedroom with an en-suite bathroom boasts a gigantic loft, perfect for additional living or office space. The possibilities are endless. Enjoy the amenities Queens Landing has to offer - outdoor waterfront pool, gym, walking paths, clubhouse, kayak launch and more. Enjoy restaurants in walking distance and Freedom boat club out of Castle Marina! 9 Queen Victoria Way, Chester Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$4,500 2 Beds ⋅ 3 Baths Highly sought after first-floor condo shows like a model home. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. Move-in ready and meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown molding, recessed lighting, and direct views of the lush greenspace with seasonal water glimpses. The gourmet kitchen and dining area are ideal for entertaining, offering a spacious island with seating, quartz countertops/bar, sleek wifi enabled appliances, and seamless flow into the living room. Unwind by the cozy fireplace or open the double sliding glass doors to your private patio—perfect for watching the sunrise, morning coffee, reading, or simply enjoying the peaceful natural setting. The owner’s suite offers both a walk-in and secondary closet, private patio access, and a luxurious en-suite bath with dual sinks and a spa-inspired frameless glass shower. The guest suite is bright and spacious, complete with its own en-suite bath, custom tilework, and large vanity. A bonus room with upgraded frosted glass doors provides the perfect space for a home office, workout area, or reading nook. Additional highlights include: LVP flooring throughout the entire home, interior access to a private one-car garage, and a secure storage unit. From your patio, take a stroll along the walking trail where you can take in the sights and sounds of nature to discover tranquil views and your kayak launch. The community also has direct access to the Kent Island Cross Island Trail. Many extra amenities to enjoy including an indoor heated pool, outdoor infinity pool, firepits, pickleball and tennis courts, dog park, and beautiful walking and biking trails. Live every day like you’re on vacation—this stunning condo offers the lifestyle you’ve been waiting for and is a must see to experience all of the upgrades! Owner pays condo, water and sewer fees. All other utilities are paid by a tenant. No pets. 3000 Herons Nest Way Unit #11, Chester Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$2,890 4 Beds ⋅ 3 Baths IMMEDIATE OCCUPANCY. Gorgeous and spacious, new paint and carpet. 4 bedroom, 2.5 bath home on the south side of Centreville and close to Rt 301. Huge master bedroom with attached master bath with separate soaking tub, shower stall and walk in closet. Gas fireplace in family room. Fixed staircase to additional storage in attic and triple pane windows throughout the house to keep down the utility bills. Large back deck overlooking fenced in yard. Covered front porch overlooking neighborhood and quiet cul-de-sac. Close to restaurants, grocery shopping and other town amenities! Don't miss this one, Apply quickly. Long term leases encouraged. No cats. 212 Frederick Dr, Centreville Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$2,200 3 Beds ⋅ 1 Baths Welcome to Kent Island Estates! THIS Home is two units. The top unit is for rent. Nestled among the trees in a peaceful waterfront community, this spacious upper-level rental offers the perfect blend of privacy, nature, & convenience. This well-maintained three-bedroom, one-bath home features a private washer & dryer in the unit, access to the front porch & rear deck, & use of the front yard. Tenants will also have use of one-half of the driveway for parking. Tenant is responsible for electric and oil. Owner will pay for water, sewer, trash, internet and lawn care. Backyard is not included in the rental. Pets will be considered on a case-by-case basis. Pet rent is $50 per month. It is walled off. No entry to the top level from the bottom level. Enjoy all that Kent Island Estates has to offer, including a community fishing pier, three private beaches, kayak access, playground, and a beach within walking distance of the home. Outdoor enthusiasts will appreciate being surrounded by the Chesapeake Bay on both sides of Kent Island, with a bike park just six miles away and endless opportunities for boating, fishing, kayaking, and exploring nature. Conveniently located near major commuter routes, shopping, restaurants, & local attractions, this home offers a quiet wooded setting while remaining close to everything you need. Don't miss this opportunity to enjoy island living in one of Kent Island's most desirable waterfront communities! 301 Wicomico Rd, Stevensville Listing courtesy of RE/MAX Leading Edge. Contact:
$4,300 2 Beds ⋅ 2 Baths AVAILABLE FOR RENT JULY 1ST-- RARE RENTAL in sought- after water-oriented Four Seasons- Ready to "try-on" coveted 'Four Seasons'? Treat yourself to this STUNNING beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-floor plan nearly 2200 SF, with generously-sized primary suite & spa-like bath with walk-in-closet, double sinks & walk-in-shower. 2nd bedroom & bath across home offers privacy for guests. Custom barn doors open to bonus space- easily used for 3rd bedroom space or office! White & bright kitchen with gleaming white quartz countertops, shiny stainless steel appliances, cabinetry to ceiling with ample storage, & large center island poised to entertain. 10-13' ceilings- Throughout! Soaring entryway, 10' min ceiling height & tray ceilings create an airy feeling, hard to match and perfect to catch the island breezes. Screened porch extends outdoor living space & overlooks new outdoor patio with built-in grill just begging to host family & friends! Attached 2-car garage with bonus storage space for a total of 550 SF makes storage easy. Customized touches in plantation shutters, Roman shades, customized, coastal paint create a designer-feel as soon as you step through the door! Located on the scenic Chester River, Four Seasons of Kent Island offers an abundance of activities for the 55 and better, OWNER PAYS MONTHLY DUES! Relax and enjoy outdoor infinity pool, indoor pool, fitness center, 24,000 SF clubhouse, ample events, walking/jogging trail, walking distance to Cross-Island trail, minutes from Bay Bridge & waterfront restaurants, dockside bars, health care centers & shopping. AVAILABLE: JULY 1ST, 6-9 month rentals considered; tenancy to end by 3-31-2027. APPLY HERE: https://apply.link/V1flS-M 137 Warbler Way, Chester Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$3,000 3 Beds ⋅ 2 Baths Spacious furnished 3 bed 2 bath rental. New flooring throughout, generous size kitchen and dining area, washer /dryer. Seeking a well-qualified tenant ,no pets, no smoking, RentSpree Application. (will rent unfurnished) 108 Wilson Rd, Grasonville Listing courtesy of Keller Williams Flagship. Contact:
$2,695 2 Beds ⋅ 2 Baths # 3809 Main St, Grasonville, MD 21638 — For Rent Welcome to this stunning, never-lived-in home newly constructed from the ground up in the heart of Grasonville! This charming 2-bedroom, 2-bathroom residence blends modern craftsmanship with thoughtful design, offering a fresh and inviting living experience from day one. Step inside to discover a beautifully appointed kitchen featuring all-new appliances, including a dishwasher and garbage disposal. A generous laundry room provides ample storage alongside a new gas-powered heating and water system, while energy-efficient mini splits deliver year-round comfort with both heating and cooling throughout the home. The expansive first-floor bedroom serves as a serene owner's retreat, while an impressive finished attic room on the upper level offers versatile space perfect for sleeping, studying, a home office, or pursuing your favorite hobbies. Storage will never be a concern thanks to easily accessible attic space that accommodates all your belongings. Outside, a brand-new private deck overlooks a partially wooded 0.3-acre backyard filled with natural shade — ideal for relaxing or entertaining. Off-street parking accommodates at least six vehicles, making gatherings effortless. The location is unbeatable. Situated just 15 minutes from the Bay Bridge and only a mile from restaurants, fishing piers, walking trails, beach access, and golf courses. Nearby Long Point Park offers outdoor recreation, while convenient grocery shopping at Safeway is just a short drive away. This is Eastern Shore living at its finest. Schedule your showing today! 3809 Main St, Grasonville Listing courtesy of Fairfax Realty of Tysons. Contact:
$1,800 2 Beds ⋅ 1 Baths If you’ve been searching for an open‑concept apartment with a stunning view, your search ends here. This fully renovated third‑floor residence delivers modern style, thoughtful updates, and an airy layout that feels instantly welcoming. Step into a beautifully redesigned kitchen featuring ample cabinetry, upgraded appliances, and a spacious island perfect for cooking, gathering, or entertaining. The open kitchen, living, and dining areas flow seamlessly together, filled with natural light from large windows that brighten the entire space. Down the hall, you’ll find two comfortable bedrooms and a full, updated bathroom, offering both privacy and convenience. And when you’re ready to unwind, step out onto the balcony and take in the refreshing, picturesque views of the Chester River—a daily reminder of the beauty just outside your door. 7501 Church Hill Rd Unit #5, Chestertown Listing courtesy of Brenton Realty Group. Contact: 4104794663