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, 100 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.

5 out of 5 average rating, 191 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

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

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.

5 out of 5 average rating, 104 reviews

A spacious living area, featuring a small sectional couch facing a TV mounted on the wall. A foosball table occupies the foreground, while a dining nook with a round table and chairs is visible in the background. Soft artificial lighting enhances the relaxed setting.

Home in Crownsville

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

4.97 out of 5 average rating, 470 reviews

A single-story house is nestled among mature trees, featuring a welcoming front porch with steps leading to the entrance. The exterior displays a clean white facade, complemented by blue shutters and a brick chimney. A brick pathway winds through the landscaped yard.

Home in Glen Burnie

Secluded acre near BWI and Baltimore

Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

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, 128 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 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.

4.95 out of 5 average rating, 104 reviews

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

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

4.9 out of 5 average rating, 220 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.

A well-decorated bedroom features a spacious bed with neutral bedding. Nearby, a dresser with multiple drawers provides storage. Dual windows allow natural light, complemented by blinds for privacy. A vibrant area rug adds a pop of color, while a ceiling fan enhances air circulation.

4.92 out of 5 average rating, 248 reviews

Relax on Kent Island in 4 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 4 Bedroom Home with a view of the Chesapeake Bay! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets or Parties & 11 max guests (8 max adults). Book Today!

4.97 out of 5 average rating, 165 reviews

A charming single-story house is framed by vibrant pink flowering trees. The facade features yellow siding, blue shutters, and a turquoise front door. A white picket fence encloses the front yard, which is well-maintained with green grass and landscaping.

Home in North Beach

Beach Home | King Bds | Firepit | Backyard Dining

Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

4.97 out of 5 average rating, 210 reviews

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.

Home in Annapolis

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, 310 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.

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.

4.78 out of 5 average rating, 23 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

4.94 out of 5 average rating, 32 reviews

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.

Home in Annapolis

The General's House

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

4.87 out of 5 average rating, 188 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

The exterior of the home showcases a two-story structure with light-colored siding, surrounded by a well-manicured lawn. A wooden ramp leads to the entrance, and garden beds with shrubs are visible. A bird feeder stands near a decorative stone feature in the green yard.

5 out of 5 average rating, 41 reviews

Wildbluesea Retreat

4.99 out of 5 average rating, 234 reviews

A dining area features a glass-top table surrounded by rustic chairs. Sunlight filters through large windows, illuminating a vase of colorful flowers. The comfortable seating area, positioned by the windows, offers views of the bay, enhancing the tranquil ambiance.

Home in Tracys Landing

The Little Gypsy BoHome

Weekly house rentals

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

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, 42 reviews

Spacious4BR home with waterviews

4.93 out of 5 average rating, 61 reviews

A spacious bedroom features large windows overlooking the waterfront, allowing natural light to fill the room. A neatly made bed with white linens is paired with a bedside table and lamp. The warm wooden flooring adds a touch of comfort to the serene atmosphere.

Home in Riva

Waterfront Annapolis Getaway!

A serene beach scene is captured at sunset, with gentle waves lapping against the shore. Rocky outcroppings frame the sandy beach, while trees cast dappled shadows in the foreground. The sky displays shades of orange and pink as the sun dips below the horizon.

4.93 out of 5 average rating, 44 reviews

Carolina Cottage - 2 story, pet-free home

4.96 out of 5 average rating, 25 reviews

An aerial view showcases the stunning Heron House nestled on a waterfront point, surrounded by lush greenery and water. A spacious deck with outdoor seating and dining is visible, along with nearby boats docked along the shoreline under a twilight sky.

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

4.99 out of 5 average rating, 73 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

4.96 out of 5 average rating, 55 reviews

A serene waterfront view captures a sunset over Crab Alley Bay, reflecting warm colors on the water. A private pier extends into the bay, with a boat anchored nearby. Lush green grass leads to the water's edge, framed by trees in the background.

Home in Chester

A waterfront Paradise with hot tub

4.98 out of 5 average rating, 49 reviews

A living area features a comfortable sectional sofa and a modern accent chair, centered around a round coffee table. Light wood flooring complements the space, while tall windows are dressed with blue curtains. Decorative lamps and minimalist wall art enhance the room's design.

Home in Edgewater

3 BRs House+Patio+Playground

Private house rentals

4.94 out of 5 average rating, 36 reviews

A serene outdoor space features two turquoise Adirondack chairs positioned on a grassy area by the water. A small white table sits between them. A fire pit is placed nearby, surrounded by trees, with a view of the calm water and distant houses.

Home in Dundalk

Waterfront Villa , 3 bedroom & theater/Game room

4.96 out of 5 average rating, 77 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

4.93 out of 5 average rating, 28 reviews

A welcoming single-story home with a light green exterior and brick accents is seen. The front yard features well-maintained shrubs and a lawn with fallen leaves. Large windows allow natural light to illuminate the interior, and a porch leads to the front door.

Home in Glen Burnie

Glen Burnie Hideaway

Superhost

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

4.86 out of 5 average rating, 21 reviews

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

4.96 out of 5 average rating, 91 reviews

A hot tub bubbles gently in the foreground, surrounded by lush greenery and a view of the waterfront. Twinkling string lights hang above the screened porch, which features a spacious dining area. The sunset casts a warm glow over the scenic landscape.

Home in Chestertown

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

A spacious waterfront home is shown against a backdrop of Chesapeake Bay. The property features well-maintained landscaping with colorful flower beds and lush green lawns. Nearby trees provide shade, and the gleaming water is visible in the distance, enhancing the serene coastal atmosphere.

4.98 out of 5 average rating, 46 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

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

The exterior of the home features a combination of navy blue and light-colored siding. A two-car garage is visible on the left side, with flags displayed on the front. Well-maintained landscaping surrounds the driveway and leads to a spacious yard.