House vacation 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, 112 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.

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, 35 reviews

Chessie Cottage - Chesapeake Bay

Welcome to Chessie Cottage on The Bay! Exit Bay Bridge, an easy 4-mile drive to our neighborhood, & the final bend in the road, our private parking. Access the house via a brick walkway to a true cottage entrance; a gabled roof over mahogany arched Dutch door, a true storybook welcome! Bay views greet you before ever entering the cottage, visible from the Dutch door straight through the west facing wall of windows overlooking the Bay. Follow our story on insta. at: propertystalkerconfessions

4.95 out of 5 average rating, 251 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

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

4.95 out of 5 average rating, 306 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, 108 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)

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.

4.97 out of 5 average rating, 121 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, 144 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.

4.95 out of 5 average rating, 105 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

Treat yourself to a luxury getaway with a 6-person hot tub, poker room with record player, and a gorgeously renovated bathroom with a freestanding soaking tub. This opulently decorated, spacious, renovated townhouse is located in the heart of very safe Fells Point. Sleeping arrangements for 6. Blazing fast 1GB Wifi, dedicated work space, 1 street parking permit, 65" Smart TV, and only 3 short blocks (3 min walk) to the bustling Fells Point waterfront. Just far enough to sleep undisturbed!

4.96 out of 5 average rating, 112 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!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

4.98 out of 5 average rating, 144 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!

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, 352 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!

5 out of 5 average rating, 209 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

Popular amenities for Stevensville house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.82 out of 5 average rating, 169 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

4.96 out of 5 average rating, 137 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 Perfect for Families!

4.98 out of 5 average rating, 105 reviews

An aerial view of a spacious red farmhouse surrounded by lush greenery and open fields. A saltwater pool is visible in the backyard, complemented by a patio area. The landscape includes manicured lawns and trees, creating a serene rural setting.

Home in Queen Anne

Farmhouse w/hot tub, close to Tuckohoe State Park

Superhost

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

4.86 out of 5 average rating, 220 reviews

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

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, 32 reviews

Bay Bliss House

4.86 out of 5 average rating, 110 reviews

Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

5 out of 5 average rating, 17 reviews

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

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, 41 reviews

Bayside Escape

Weekly house rentals

A screened lanai features a dining table surrounded by comfortable striped chairs. A hanging chair is positioned to one side, providing additional seating. Natural light floods the space through the open design, with a view of the spacious backyard and surrounding trees.

4.98 out of 5 average rating, 85 reviews

Cozy home with Screened Porch, Min from Weddings

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.

4.97 out of 5 average rating, 59 reviews

Spacious4BR home with waterviews

Aerial view of a waterfront property featuring a sandy beach that meets the Chesapeake Bay. The landscaped yard is visible, along with a marina and boats moored nearby. The back of the home can be seen, which is surrounded by trees, providing a serene setting.

5 out of 5 average rating, 10 reviews

Private Beach and Bay Views at One-Level Home

5 out of 5 average rating, 67 reviews

Away at the Bay: New Home on the Chesapeake Bay!

4.97 out of 5 average rating, 38 reviews

Two black Adirondack chairs are positioned on a stone patio, facing a serene sunset over the bay. A small table with a decorative metal base is placed between the chairs. The silhouette of a tall tree is visible against the vibrant dusk sky.

Home in Chester

Kent Island Escape

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.

4.96 out of 5 average rating, 89 reviews

Kent Island Beach House II by Kentmorr Marina

A well-lit living area features comfortable seating on a soft gray sofa, complemented by a wooden coffee table and a television mounted on the wall. A ceiling fan is present above, and natural light filters in through large windows, creating an inviting space.

4.98 out of 5 average rating, 50 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, 81 reviews

Bayview Bungalow - Water view, EV charging station

Private house rentals

4.97 out of 5 average rating, 98 reviews

Home in Annapolis

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

5 out of 5 average rating, 86 reviews

Home in Grasonville

Bay Breeze - 3BR Waterfront Chester River Retreat

4.93 out of 5 average rating, 30 reviews

Home in Rock Hall

Chesapeake Bay Retreat W/Breathtaking Views

4.98 out of 5 average rating, 61 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

4.97 out of 5 average rating, 39 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, 78 reviews

Adirondack chairs are arranged on the grassy waterfront, facing a serene view of the river at sunset. The sky displays a blend of warm orange and soft purple hues. A private pier extends into the water, with a boat docked nearby and calm reflections on the surface.

Home in Shady Side

Sunset Cottage

A spacious deck with a wooden surface overlooks the water, framed by a black railing. The sky displays a mix of clouds and blue, enhancing the tranquil atmosphere. The waterfront setting offers a view of the shoreline and distant docks.

4.95 out of 5 average rating, 37 reviews

Bayou on the Bay

A serene outdoor space features six Adirondack chairs facing the sunset over the bay. The horizon is lined with soft clouds, and a picnic table is set in the distance on a grassy area, providing a perfect spot for relaxation.