House holiday rentals in Stevensville

A charming gray house is situated beside a manicured lawn, featuring a well-maintained driveway and an adjacent garage. Green shrubs and small trees are positioned around the property, creating a welcoming environment. A clear blue sky with fluffy clouds is visible overhead.

4.91 out of 5 average rating, 101 reviews

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

4.95 out of 5 average rating, 291 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.

4.98 out of 5 average rating, 170 reviews

Two adirondack chairs in blue and teal are positioned on a wooden pier, facing the sunset over calm waters. A small white table sits between them, holding two coffee mugs. The vibrant orange and pink hues of the sky reflect on the water's surface.

Home in Edgewater

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

4.96 out of 5 average rating, 111 reviews

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

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.

4.99 out of 5 average rating, 131 reviews

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 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.

4.93 out of 5 average rating, 322 reviews

❤️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!

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.

4.9 out of 5 average rating, 221 reviews

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.

The exterior of a two-story house is framed by mature trees, complemented by a wide concrete driveway. A welcoming front porch with multiple steps leads to the entrance, and landscaped areas surround the home, enhancing its natural setting.

4.96 out of 5 average rating, 103 reviews

Serene Riverfront Home

A private setting with river and marshland views where fox, heron, and osprey sightings are common. Sip coffee in front of the gas fireplace while watching the sun rise on the water's horizon. Conveniently located in the community of Cape St Claire walking distance to grocery and restaurants. Easy access to Route 50 and only 15 minutes to downtown Annapolis and the US Naval Academy.

A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.

4.96 out of 5 average rating, 218 reviews

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.

5 out of 5 average rating, 313 reviews

The outdoor area features a circular pool surrounded by colorful lounge chairs in yellow, blue, and white. Umbrellas in red and blue provide shade over a dining table with red chairs. Towering trees frame the view of the expansive waterfront beyond.

Home in Kent Narrows

Chester Riverfront At Kent Narrows

Our place is spacious, has great water views, a private beach and is close to restaurants and dining. You’ll love it because of the bay, hot tub, pool, and outdoor space. Our place is good for couples, friends, solo adventurers, and families with kids.

4.97 out of 5 average rating, 110 reviews

A bright living space is characterized by light blue walls and hardwood flooring. A brown recliner and a wooden coffee table are present, along with a turquoise entertainment unit housing a television. Natural light fills the room through multiple windows, enhancing the inviting atmosphere.

Home in Chestertown

2 Beds, 2.5 Baths - Perfect Downtown Location

Quaint and charming, our home away from home in historic Chestertown features 2 bedrooms and 2.5 bathrooms and can accommodate up to 4 adults. Just a few blocks from the downtown shops and restaurants. Also walkable to Washington College.

A shaded seating area is arranged under a gazebo, featuring a woven outdoor sofa and chairs in warm orange cushions. A central fire pit table complements the setting, surrounded by a patterned outdoor rug on a paved surface, with a fenced backyard visible in the background.

4.99 out of 5 average rating, 120 reviews

Nautical Retreat 6 Guests • 3 BDR • 2 Baths

*Flexible Commissioning Week Cancellation Policy* ✔ Westfield Mall - 1 mile ✔ Hospital - 1.2 miles ✔ Navy-Marine Corps Memorial Stadium - 1.5 miles ✔ U.S. Naval Academy – 3 miles ✔ Washington, DC – 30 miles ✔ Baltimore - 30 miles

Popular amenities for house rentals in Stevensville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

An aerial view of a waterfront home is displayed, featuring a private swimming pool in the yard and a dock extending into the water. Surrounding trees and neighboring homes create a peaceful residential environment. The blue expanse of the water complements the green landscape.

4.76 out of 5 average rating, 25 reviews

Waterfront Escape with Pool Nature Lover Paradise

Superhost

A winding stone pathway leads through a vast green lawn towards the shimmering waters of the eastern Chesapeake Bay. Two comfortable lounge chairs are positioned at the water's edge, offering a serene view of the horizon under a soft blue sky.

Home in Queenstown

4.81 out of 5 average rating, 164 reviews

Bay Breeze Retreat

A modern two-story home is showcased with a well-maintained lawn and landscaped flower beds. The façade features a mixture of siding and brick, complemented by large windows and a welcoming front porch with double doors.

4.94 out of 5 average rating, 32 reviews

The General's House-Spacious Home w/Pool & Hot Tub

4.97 out of 5 average rating, 126 reviews

An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.

Home in Cambridge

Gorgeous, Waterfront Home Is Fabulous in Winter!

An aerial view captures the expansive backyard of the waterfront property, featuring a private outdoor pool and a long fishing pier along the shoreline. Lush green grass surrounds the home, with neighboring houses visible in the background, set against a backdrop of serene water.

4.94 out of 5 average rating, 18 reviews

Kent Island Waterfront Retreat

4.88 out of 5 average rating, 195 reviews

A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.

Home in Severn

Large Home with Pool & 7 bedrooms; sleeps 21

The exterior of the house features a combination of natural stone and shingle siding. A well-maintained garden with flowering shrubs borders the walkway. A small porch is visible, providing access to the entrance, all under a clear blue sky.

5 out of 5 average rating, 20 reviews

Bay Bliss House

Superhost

A stylish dining area is showcased, featuring a long table set for a meal. Generous seating is provided by a custom velvet upholstered bench with decorative pillows, while a modern light fixture hangs above. Large windows allow natural light to fill the space.

Home in Bowie

4.87 out of 5 average rating, 103 reviews

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

Weekly house rentals

4.93 out of 5 average rating, 56 reviews

An aerial view captures the nearby marina and lush greenery surrounding the property. The calm waters of the bay reflect the clear blue sky, while residential buildings and open fields are visible, indicating a tranquil environment close to the coast.

Home in Rock Hall

Historic Cottage | 1min DT | Views | W/D | Parking

5 out of 5 average rating, 8 reviews

A private dock extends over calm water, featuring two white Adirondack chairs positioned for serene views. Lush greenery borders the water, creating a tranquil setting. A red mat is placed on the dock, adding a pop of color to the natural surroundings.

Home in Chester

Harbor House

5 out of 5 average rating, 75 reviews

A spacious living area is highlighted by a prominent stone fireplace, offering a cozy focal point. Two comfortable sofas are positioned around a light wood coffee table, which holds a decorative plant. Soft natural light fills the room from large windows, enhancing the welcoming ambiance.

Home in Grasonville

Bay Breeze - 3BR Waterfront Chester River Retreat

A stately home with a light grey exterior is set amidst greenery, featuring a welcoming front porch with white railings. Flanking the porch, flowerbeds with small plants and flags add charm. A gravel driveway leads to a detached garage, enhancing the property's inviting appeal.

5 out of 5 average rating, 42 reviews

Screened Porch | Near Bay Bridge & USNA | Big Yard

A modern kitchen features navy blue cabinetry and white countertops. Stainless steel appliances include a refrigerator and gas stove. A central island provides seating with two wooden stools. The backsplash is adorned with a mosaic pattern, enhancing the kitchen's contemporary design.

5 out of 5 average rating, 71 reviews

Bayview Bungalow - Water view, EV charging station

An inviting outdoor space is illuminated by string lights, creating a cozy ambiance. Lush greenery surrounds a small palm, leading the eye toward a serene waterfront view under a twilight sky.

4.87 out of 5 average rating, 79 reviews

Kent Island Waterfront Home

A charming bayfront home is nestled in a landscaped yard. The exterior features blue siding, a welcoming front porch, and well-maintained gardens. An American flag is displayed prominently, while a sidewalk leads up to the entrance, surrounded by lush greenery and colorful flower beds.

4.95 out of 5 average rating, 20 reviews

Bay Views Just Minutes from Annapolis

An aerial view captures a spacious vacation home surrounded by lush greenery and scenic landscapes. A serene tidal pond reflects the sky, while the property features a well-maintained lawn leading to views of the water. The architectural detail of the home is complemented by outdoor seating areas.

5 out of 5 average rating, 70 reviews

Love Point Idyll - 240' Private Beachfront

Private house rentals

An aerial view captures a spacious yard illuminated by soft string lights, featuring a circular stone fire pit surrounded by Adirondack chairs. Lush greenery and flowering trees provide a natural backdrop, with the bay visible in the distance under a colorful sunset sky.

4.98 out of 5 average rating, 46 reviews

Spacious4BR home with waterviews

The living area is arranged with various seating options, including a bright orange couch and green chairs. A large area rug anchors the space, complemented by a coffee table and side tables. Windows offer expansive views of the bay, filling the room with natural light.

5 out of 5 average rating, 31 reviews

Chessie Cottage - Chesapeake Bay

4.95 out of 5 average rating, 96 reviews

An open layout living area features a kitchen equipped with stainless steel appliances and a breakfast bar with high stools. A dining table is visible in the background near large windows. The space is complemented by two leather couches and light hardwood flooring.

Home in Arnold

Rachel's BnB

5 out of 5 average rating, 46 reviews

A wooden dock extends over the water, featuring two white Adirondack chairs positioned for relaxed seating. The serene water stretches toward the horizon, while the sky is dotted with fluffy clouds, creating a calming outdoor retreat.

Home in Chester

*Waterfront Sunset Bayview* sleeps 6

4.88 out of 5 average rating, 25 reviews

A spacious living room features a large, L-shaped sectional sofa adorned with decorative pillows. A coffee table sits centered on a patterned area rug. Natural light enters through windows, and a potted plant adds a touch of greenery. Ceiling fans provide ventilation while maintaining a relaxed atmosphere.

Home in Shady Side

The Wise Quack 2 - A Taste of the Chesapeake Bay!

The living room showcases large windows that provide ample natural light and offer views of the surrounding area. A comfortable blue velvet sofa is paired with two light-colored armchairs and a wooden coffee table, creating a welcoming seating arrangement on a light-colored area rug.

4.94 out of 5 average rating, 16 reviews

Cozy Cottage

4.99 out of 5 average rating, 76 reviews

A single-level home in a serene setting is viewed from the water. The exterior is clad in light blue with large windows. A shaded area is present for outdoor seating. Kayaks are stored nearby, and a wooden dock extends into the calm water.

Home in Pasadena

Waterfront CHeerful 2 with Private home