Waterfront holiday rentals in Stevensville

4.96 out of 5 average rating, 435 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

4.95 out of 5 average rating, 290 reviews

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

4.99 out of 5 average rating, 129 reviews

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

A round swimming pool is centrally located, surrounded by lounge chairs and a wooden deck. Sailboats are visible in the marina beyond, with lush greenery lining the water's edge. An umbrella provides shade over a seating area, adding to the tranquil outdoor setting.

4.96 out of 5 average rating, 313 reviews

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW SUMMER 2026 SPRING and FALL BOAT SHOW 1 bed/bath condo, sleeps 4 max, covered comfortable water facing deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy Football, .25 mi. to boatshows! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another location.

4.93 out of 5 average rating, 320 reviews

A spacious living room features a large sectional sofa, a coffee table, and a TV stand. Natural light enters through multiple windows, illuminating the wood flooring. An open view leads towards the kitchen area, where bar stools are positioned at a counter.

Home in Stevensville

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax in this Stylish Coastal-Country Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups! We're conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets or Parties & 14 max guests (8 max adults). Book Today!

4.9 out of 5 average rating, 221 reviews

A tranquil view of the Chesapeake Bay is captured, showcasing a grassy expanse leading to the water. Two stone boundary walls are visible, framing the lush landscape. A solitary beach umbrella and chair rest on the shore, inviting relaxation by the calm water.

Home in Annapolis

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

5 out of 5 average rating, 252 reviews

A driveway leads to the garage of a two-story apartment building, framed by greenery on either side. The smooth, paved surface is bordered by neatly arranged flower beds and trees, with sunlight casting gentle shadows along the path.

Guest suite in Annapolis

Cape St Claire waterfront getaway "The Apartment"

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

Cottage in Saint Michaels

A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.

4.97 out of 5 average rating, 178 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Guesthouse in Stevensville

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

4.99 out of 5 average rating, 317 reviews

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.91 out of 5 average rating, 620 reviews

A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.

Apartment in Deale

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis or other local walks. Fully relax with pier, kayaks, hot tub, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

4.98 out of 5 average rating, 657 reviews

A serene riverfront scene features a reflecting water surface, with the sky painted in soft pinks and purples at sunset. Lush greenery borders the water's edge, and silhouettes of trees frame the tranquil landscape.

Guest suite in Pasadena

Sea Dreamer

Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Place to stay in Glen Burnie

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

4.93 out of 5 average rating, 373 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Popular amenities for Stevensville waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.96 out of 5 average rating, 113 reviews

A two-story building is shown, featuring a metal roof and a wooden balcony adorned with potted plants. Outdoor furniture is visible on the balcony, and multiple windows can be seen on the building's exterior.

Apartment in Chestertown

RIVER WATCH

4.97 out of 5 average rating, 39 reviews

A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.

Apartment in Pasadena

Relaxing Waterfront Apartment!

4.98 out of 5 average rating, 128 reviews

A serene view of the Severn River is captured, bordered by lush greenery and blooming flowers. The calm water reflects the sky and surrounding landscape, while trees create a natural frame. Sunlight casts gentle shadows over the grassy area, enhancing the tranquil setting.

Apartment in Annapolis

One bedroom apartment in Annapolis

Apartment in Stevensville

An aerial view showcases a large grassy area surrounding a heated pool, with several lounge chairs positioned nearby. A fire pit is set with white adirondack chairs. Two properties are visible, featuring balconies and umbrellas enhancing the outdoor space.

5 out of 5 average rating, 71 reviews

Heron Roost

4.96 out of 5 average rating, 185 reviews

Apartment in Arnold

Celebrate Summer In Your Private Pool & Hot tub

4.97 out of 5 average rating, 288 reviews

A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.

Apartment in Essex

A place unique on sue creek

4.97 out of 5 average rating, 32 reviews

A serene sunset is viewed over calm waters, reflecting warm orange and gold hues. Silhouettes of trees and a boat dock are visible in the foreground, with a few boats gently resting on the still water.

Apartment in Dundalk

Waterfront Romantic Studio

Apartment in Inner Harbor

A comfortable living room is shown, featuring a large gray sectional sofa and a wall-mounted television. A coffee table is positioned in front of the sofa, where a lit candle adds a subtle touch. Dining settings are arranged on the table nearby, and natural light enters through the window.

5 out of 5 average rating, 11 reviews

Waterfront + parking and gym

Waterfront house rentals

4.93 out of 5 average rating, 109 reviews

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

River House on the Choptank

4.95 out of 5 average rating, 216 reviews

Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

Annapolis Area Waterside Retreat

5 out of 5 average rating, 194 reviews

The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

4.92 out of 5 average rating, 109 reviews

A waterfront home is showcased, featuring a multi-level design with balconies offering views of the water. The landscaped yard is bordered by greenery, while wooden pilings line the shore. Adjacent properties are visible, contributing to a harmonious neighborhood setting.

Home in Annapolis

Waterfront Oasis in Eastport-Easy Walk to Downtown

4.98 out of 5 average rating, 127 reviews

A tranquil riverside scene at sunset is captured, with silhouettes of trees against a vibrant sky. The calm water reflects the warm tones of the sunset. A pier is visible in the background, framed by the natural landscape, creating a serene ambience.

Home in Deale

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

4.96 out of 5 average rating, 164 reviews

A screened-in porch provides a serene setting with two wicker chairs facing a small table. Peaceful views of the calm waterfront and surrounding greenery are visible, enhancing the connection with nature.

Home in Glen Burnie

12 M to Naval Acadmey | Waterfront

4.95 out of 5 average rating, 109 reviews

A wooden deck area is highlighted with four Adirondack chairs arranged around a central fire table, where flames flicker gently. Beyond the deck, a well-maintained lawn leads to the bay, visible in the distance under a colorful sunset sky.

Home in Stevensville

25-50% Off~Private Beach~Hot Tub~Fire Table~

Home in Federal Hill - Montgomery

A cozy living room features a white sectional sofa paired with two warm-toned armchairs. A coffee table sits in the center, adorned with a decorative plant. Exposed brick walls add character, while natural light fills the space through nearby windows and a door.

4.96 out of 5 average rating, 204 reviews

Luxury Fed Hill Home w/Rooftop & 4 Parking Spots

Waterfront condo accommodation

Superhost

A modern living area features a sleek flat-screen television mounted above a stone fireplace. On either side, wooden shelving units are filled with decorative items and books. The ambient light from the fireplace creates a cozy atmosphere, complemented by neutral wall colors.

Condo in Inner Harbor

4.88 out of 5 average rating, 260 reviews

Historic Federal hills urban lifestyle

A light-filled living area features a comfortable sectional sofa with pillows and a cozy throw. A round coffee table sits in the center, surrounded by a woven basket and a wooden armchair. The kitchen area is visible in the background, equipped with dark cabinetry and stainless-steel appliances.

4.75 out of 5 average rating, 85 reviews

Amazing Views from Spa Creek 2BD Condo with Pool

4.98 out of 5 average rating, 103 reviews

Charming Annapolis Waterfront Condo

4.2 out of 5 average rating, 10 reviews

Upscale Waterfront Condo Annapolis

A modern living area features a large sectional sofa in deep blue, paired with a wooden coffee table. Natural light streams through floor-to-ceiling windows, providing views of the city. A comfortable chair is positioned nearby, with a stylish console beneath a mounted television.

Condo in Inner Harbor

4.33 out of 5 average rating, 6 reviews

Downtown Baltimore Vacation Waterfront

Superhost

The living area features a comfortable blue sectional sofa paired with a light-colored accent chair. A round metallic coffee table rests on a patterned area rug. Two lamps with white shades provide soft lighting, while large windows offer natural light and views of the outdoors.

4.78 out of 5 average rating, 9 reviews

Prime Location Waterfront Eastport Condo w Parking

Superhost

5 out of 5 average rating, 3 reviews

Waterfront Suite w Scenic Annapolis Views