House holiday rentals in Centreville

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Cattail Landing- Photographer's Waterfront Retreat

Accepting 2025 bookings as of May 1st.... "Cattail Landing" Spring is here, with beautiful sunsets, new foliage on the trees, and our nest of Bald Eagles! Take our kayaks to explore, or go fishing off our landing. In the afternoon enjoy the magnificent sunsets, a drink on the deck, our outdoor hot tub and/or fireplace. A waterfront retreat on 2 acres in a spacious, charming house on the Western Shore of the Chesapeake Bay. Great for a couples getaway, family reunion, or work from home.

Full house in “coolest neighborhood in America”

Small but cozy single family in Northern Baltimore, located in the very sought after Hampden neighborhood. 5 minute walk to “the Avenue” and 34th Street lights at Xmas. Directly across the street is a Walgreen’s, MOM’s Organic Market, gym, restaurants, UPS Store, etc. A private driveway, manicured back yard w/ hardscape, fire pit and tons of indoor amenities offer a convenient and relaxing stay in this quaint Baltimore hood. Cleaned by COVID-trained professionals after each reservation.

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Eastport Haven House

Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best restaurants ( Ruth's Chris, ChartHouse , Vin 909 and many many others )and home to some very famous neighbors it's one one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping USNA . Very spacious home with 4 bedrooms 4 baths , parking for 4 cars and a pool table. Truly a million plus dollar property !

THE RIVERHOUSE @ DE TURF

THE RIVER HOUSE @ DE TURF ! 6 bedrooms and 3 full baths, this home accommodates large groups traveling to Delaware Turf for soccer, lacrosse and field hockey tournaments. Four living areas and a central kitchen, multiple families can use this home at the same time. 2 sets of bunks in each bunk room! The river view is outstanding from the picture window in the family room! This home is less than a mile from the turf fields and 30 minutes to the resort beaches!

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!