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, 103 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.

LocationFamilyCondition

4.95 out of 5 average rating, 298 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.

LocationFamilySleep quality

4.98 out of 5 average rating, 177 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 Dock!

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!

FamilyLocationBreakfast

4.98 out of 5 average rating, 102 reviews

The single-story ranch home is set on a spacious lot adorned with a mix of grass and fallen leaves. Blue shutters frame the windows, and a welcoming front porch is furnished with several chairs. A two-car garage is visible to the left.

Home in Rock Hall

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

ValueLocationComfort

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, 113 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.

ValueFamilyCheck-in

4.95 out of 5 average rating, 169 reviews

An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.

Home in Riviera Beach

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

LocationValueTV

4.81 out of 5 average rating, 164 reviews

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

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

LocationValueGetting around

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, 137 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.

LocationValueWifi

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.

4.96 out of 5 average rating, 123 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.

FamilyValueCheck-in

4.98 out of 5 average rating, 130 reviews

Home in Deale

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

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

FamilyValueView

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, 345 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!

ValueFamilyParks

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, 222 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.

LocationValueIndoor spaces

Popular amenities for house rentals in Stevensville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 130 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!

ValueFamilyPets

4.88 out of 5 average rating, 208 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 Private Pool, Gym, Sauna, 7 Bedroo

FamilyLocationGetting around

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, 21 reviews

Bay Bliss House

LocationValueCheck-in

4.86 out of 5 average rating, 113 reviews

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

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

FamilyValueHot tub

A private pool is centrally located, surrounded by a well-kept grassy yard. Lounge chairs are positioned around the pool, providing relaxation options. The two-story cottage is visible in the background, along with a shaded area and trees that create a serene setting.

4.54 out of 5 average rating, 24 reviews

Private Pool & Stunning Bay Views on Kent Island

LocationFamilyWalkability

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

LocationValueAccuracy

The outdoor pool area features a spacious salt-water pool surrounded by a stone patio. Comfortable seating is arranged on either side, with colorful landscape visible in the background and an umbrella providing shade. The skyline is adorned with hues of sunset across the bay.

5 out of 5 average rating, 31 reviews

Bayside Escape

FamilyValueKitchen

5 out of 5 average rating, 318 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

FamilyValueKitchen

Weekly house rentals

4.99 out of 5 average rating, 88 reviews

A spacious bed is adorned with decorative orange pillows and flanked by elegant bedside lamps. Framed artwork featuring floral designs hangs above the headboard, complementing the soft color palette of the room.

Home in Fells Point

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

ValueLocationWifi

4.95 out of 5 average rating, 21 reviews

The spacious living area features a warm wood ceiling and large windows overlooking the greenery outside. A comfortable sectional sofa and an accent chair are positioned around a rectangular coffee table, creating an inviting space. A modern fireplace stands elegantly against the wall, complemented by tasteful decor.

Home in Grasonville

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

LocationFamilyNearby

4.98 out of 5 average rating, 58 reviews

A spacious ranch-style house is set against a clear blue sky. The property features a circular driveway with a stone garden at its center, surrounded by various low shrubs. Neatly manicured lawns line the approach to the home's entrance, adding to the welcoming curb appeal.

Home in Queenstown

Gorgeous Creek Side Ranch-Style Estate With Dock

ValueLocationIndoor spaces

A two-story home features large windows and a spacious deck bordered by vibrant purple flowers and lush green grass. Umbrellas provide shade over the seating area, with trees adding to the serene, outdoor atmosphere. The property is set in a welcoming, landscaped setting.

4.95 out of 5 average rating, 88 reviews

Spend Mother's Day by The Bay across from Marina

LocationFamilyBeach

4.95 out of 5 average rating, 62 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

LocationFamilyTV

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, 51 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

LocationFamilyBathroom

4.83 out of 5 average rating, 18 reviews

Home in Chester

Crab Alley | Waterfront Home + Hot Tub + Game Room

LocationFamilyCheck-in

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, 73 reviews

Love Point Idyll - 240' Private Beachfront

LocationFamilyGrill

Private house rentals

A spacious living area features a large sectional sofa with yellow accent pillows and a wooden coffee table. Natural light streams through three windows, illuminating a mounted flat-screen TV and surrounding shelves that hold decorative items. A cozy atmosphere is created by warm wooden flooring.

4.88 out of 5 average rating, 17 reviews

Pet-Friendly Annapolis Stay | Near USNA & Beach

FamilyLocationDecor

The exterior of a charming historic home is illuminated at dusk, with warm lights glowing from the windows. A spacious front porch is visible, and a well-maintained garden with shrubs and plants frames the entrance. The nearby deck area features string lights for ambiance.

4.92 out of 5 average rating, 39 reviews

Waterfront Home - Amazing Views - Beach Adjacent

LocationFamilyIndoor spaces

4.93 out of 5 average rating, 58 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

ValueLocationCheck-in

5 out of 5 average rating, 9 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

FamilyLocationHiking

4.93 out of 5 average rating, 84 reviews

A spacious deck offers outdoor seating, including a large dining table and comfortable chairs, overlooking the serene waterfront. Lush trees frame the scene, and the calm water reflects the clear sky, creating a peaceful environment for relaxation.

Home in Riva

Waterfront Annapolis Getaway!

ValueLocationAccess

A spacious living area features a custom stone fireplace, surrounded by soft seating and a rustic coffee table. Large glass doors provide views of the outdoor space. A ceiling fan adds to the comfortable ambiance, while a large clock adorns the wall.

5 out of 5 average rating, 24 reviews

Marymont Cottage

FamilyLocationBack garden

4.92 out of 5 average rating, 24 reviews

Home in Rock Hall

Chesapeake Bay Retreat W/Breathtaking Views

LocationFamilyOutdoor spaces