House holiday rentals in Stevensville

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, 306 reviews

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

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. We are 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 Parties & 14 max guests. Book Today!

5 out of 5 average rating, 159 reviews

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

4.95 out of 5 average rating, 286 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

River Front house / dock/hot tub

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, 168 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!

5 out of 5 average rating, 187 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, 110 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, 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, 101 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, 219 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.

4.99 out of 5 average rating, 134 reviews

A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.

Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

The image displays a serene sunset over a calm river, with golden hues reflecting off the water's surface. Wooden posts stand along the edge of a deck, enhancing the tranquil atmosphere. Soft clouds are visible in the sky, creating a peaceful twilight scene.

4.97 out of 5 average rating, 122 reviews

The Kent Island House

Gorgeous, life filled spaces with a combo of mid-century contemporary vibe. Beautiful art work! Everything is proved for a comfy stay: comfortable beds, guest bathrobes, super kitchen. Beautiful docks, decks, flowers, and very peaceful vibes. Catch the sunrises at the end of the street and sunsets on the dock are absolutely stunning and beautiful!

4.97 out of 5 average rating, 209 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.

Popular amenities for Stevensville house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 130 reviews

A spacious waterfront home is showcased, featuring a large porch and neatly manicured lawns. The property includes a sandy beach leading to the calm waters of Fishing Creek, with a picturesque background of trees and a second building in the distance.

Home in Woolford

Starboard on McKeil Point, w/heated pool & hot tub

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

5 out of 5 average rating, 15 reviews

An aerial view captures a spacious property surrounded by lush greenery. A rectangular pool is positioned in front of a two-story structure, along with multiple lounge chairs and a swing set nearby. The expansive lawn provides an open and inviting outdoor space.

Home in Sherwood

Punch Point boasts a sandy beach w/ pool and pier

4.97 out of 5 average rating, 125 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

Come for Water Fowl, Hunting-Big, Beautiful Home!

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, 19 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, 40 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

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, 99 reviews

Cheerful & Spacious Shore Life Beauty!

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

Beach and bay views at one-level Waterfront home

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, 28 reviews

Chessie Cottage - Chesapeake Bay

5 out of 5 average rating, 71 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

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

5 out of 5 average rating, 86 reviews

A modern living area features a cozy seating arrangement with a grey sofa and chair, accented by orange pillows. A sleek coffee table sits on a soft area rug, and an electric fireplace is mounted on the wall beneath a large screen displaying visuals.

Home in Chester

Chester Delight- Fireplace/Deck&Patio+fenced yard

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, 39 reviews

Screened Porch | Near Bay Bridge & USNA | Big Yard

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

Private 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.

4.97 out of 5 average rating, 76 reviews

Cozy home with Screened Porch, Min from Weddings

4.97 out of 5 average rating, 35 reviews

Two white Adirondack chairs are placed on a grassy area, facing a calm body of water. A sliver of rainbow is visible in the sky above the horizon. Lush greenery surrounds the scene, with a large tree providing shade.

Home in Chesapeake Beach

Mid-Century Modern: Direct Private Beach Access

4.89 out of 5 average rating, 18 reviews

Large windows offer unobstructed views of Chesapeake Bay, allowing natural light to fill the space. A spacious seating area with a light-colored sofa is visible, alongside a dining table that accommodates multiple chairs. The outdoor deck can be seen through the doors, extending towards the water.

Home in Rock Hall

Chesapeake Bay Retreat W/Breathtaking Views

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

5 out of 5 average rating, 27 reviews

Home in Pasadena

Rock Creek Cottage, Waterfront

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, 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

Waterfront w/ Hot Tub + Dock | Harbor View Haven