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.

4.92 out of 5 average rating, 119 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, 314 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.

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.

4.96 out of 5 average rating, 267 reviews

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!

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, 133 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, 152 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.

4.98 out of 5 average rating, 155 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, 366 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!

4.99 out of 5 average rating, 142 reviews

A Bullfrog hot tub is situated under a wooden gazebo, with water glistening in sunlight. A plush robe is draped over the edge alongside a straw hat and a rolled towel. A grassy area and wooden privacy fence complete the serene outdoor setting.

Home in Cape St. Claire

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

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.

4.99 out of 5 average rating, 145 reviews

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

5.0 out of 5 average rating, 217 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

5.0 out of 5 average rating, 254 reviews

Home in Chestertown

The Garden Estate: Historic Town Center Home

Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.

4.97 out of 5 average rating, 113 reviews

A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.

Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

Popular amenities for Stevensville house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 329 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

4.99 out of 5 average rating, 255 reviews

A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.

Home in Tracys Landing

The Little Gypsy BoHome

A spacious backyard features a pool surrounded by a paved patio. Comfortable lounge chairs and umbrellas are positioned for relaxation. The two-story house with a deck overlooks the inviting pool area, flanked by lush greenery and colorful landscaping.

4.98 out of 5 average rating, 101 reviews

Chesapeake Bay Beach House with Pool and Hot Tub

Superhost

Home in Waldorf

Private Pool | Modern | Lux 4 BR Retreat | Near DC

4.84 out of 5 average rating, 123 reviews

4.97 out of 5 average rating, 117 reviews

A charming blue cottage is depicted with a gabled roof and white columns framing the entrance. Lush green bushes line the pathway, providing an inviting approach. Clear blue skies and tall trees are visible in the background, enhancing the peaceful setting.

Home in St. Michaels

SM's Premier Rental Heated Pool (closes 10/27)

5.0 out of 5 average rating, 28 reviews

Kent Island Waterfront | Swim Spa + Sauna + Beach

5.0 out of 5 average rating, 23 reviews

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

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.

5.0 out of 5 average rating, 42 reviews

Bay Bliss House

Weekly house rentals

4.9 out of 5 average rating, 154 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

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.

4.98 out of 5 average rating, 185 reviews

Waterfront Chesapeake Bay Sunrises & Fishing Dock!

4.96 out of 5 average rating, 268 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

4.96 out of 5 average rating, 105 reviews

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

Home in Chestertown

River front cottage with private dock & water fun

5.0 out of 5 average rating, 70 reviews

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

5.0 out of 5 average rating, 5 reviews

Island Life 2 2024 Remodeled Home

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, 55 reviews

Screened Porch | Near Bay Bridge & USNA | Big Yard

5.0 out of 5 average rating, 7 reviews

Private & Peaceful Water Views, Big Deck, Games

Private house rentals

5.0 out of 5 average rating, 89 reviews

Home in Grasonville

Bay Breeze - 3BR Waterfront Chester River Retreat

Superhost

4.63 out of 5 average rating, 38 reviews

Kent Island Luxury Waterfront

4.94 out of 5 average rating, 51 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

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, 63 reviews

Spacious4BR home with waterviews

4.96 out of 5 average rating, 84 reviews

Four light blue Adirondack chairs are arranged on a grassy area overlooking a calm body of water. A small side table is positioned between the chairs. The sky displays a gradient of soft colors as the sun sets, reflecting beautifully on the water's surface.

Home in Chester

The Fitz Inn

5.0 out of 5 average rating, 16 reviews

A two-story blue house features a welcoming front porch with white railings, inviting seating, and a symmetrical design. Lush greenery surrounds the entrance, and a well-kept lawn adds to the charm of the property. Large windows allow for ample natural light.

Home in Chester

Island Blue Getaway

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.

4.79 out of 5 average rating, 24 reviews

Bay Views Just Minutes from Annapolis

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.