Vacation rentals with a patio in Chestertown

4.95 out of 5 average rating, 152 reviews

The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.

Farm stay in Chestertown

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

4.93 out of 5 average rating, 112 reviews

The custom-built home features a blend of stone and siding, set within a grassy landscape. A covered front porch invites relaxation, while large windows allow ample natural light. Solar panels are visible on the roof, integrating sustainable energy solutions.

Farm stay in Centreville

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

4.98 out of 5 average rating, 45 reviews

The exterior of a two-story house is shown, featuring a private patio with brick flooring. A wooden table with chairs is set under a large navy umbrella, providing shade. Lush greenery surrounds the yard, and clear blue skies are visible above.

Home in Chestertown

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. And yes, we also have a 420-friendly space. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

Houseboat in Kent Narrows

A modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.

4.97 out of 5 average rating, 173 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

4.97 out of 5 average rating, 149 reviews

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Casa particular in Chestertown

A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.

4.93 out of 5 average rating, 168 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

4.96 out of 5 average rating, 132 reviews

A friendly alpaca stands in a grassy area, surrounded by a dirt patch and a large, leafless tree. Several structures are visible in the background, separated by a white fence, under a partly cloudy sky.

Home in Bel Air

Hobbit House, one-of-a-kind home

Take it easy at this unique and tranquil getaway. Located within walkable distance to Cedar Lane Sports Complex (avoid the often-long line of traffic from SR136/SR543) & short drive to Aberdeen IronBirds Stadium, this private home is one of the four homes located on a gentleman's farm. This is an awesome location with close proximity to restaurants, shopping, entertainment and healthcare. Surrounded by luxury homes, you will be hard pressed to find a better neighborhood anywhere nearby.

5 out of 5 average rating, 129 reviews

The exterior of a large, historic house is viewed from the river, surrounded by leafless trees and greenery. A deck is visible, along with a patio area featuring white chairs. The structure showcases multiple levels and a traditional architectural style.

Apartment in Chestertown

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

4.99 out of 5 average rating, 117 reviews

The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.

Home in Perry Hall

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

4.96 out of 5 average rating, 109 reviews

A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

5 out of 5 average rating, 115 reviews

The front porch features sheer white curtains draped along the railing, creating an airy atmosphere. A bright yellow door serves as a focal point, flanked by large windows above. Brick steps lead up to the entry, surrounded by neatly arranged greenery.

Home in Rock Hall

Cozy 1920's Bungalow Near Water/Local Attractions

Updated 1920's bungalow near all Rock Hall has to offer. Blocks away from the Bay, marinas and center of town. Coffee shop, grocery and other shops 2 blocks away. Walk to several restaurants. Cozy and very comfortable. Quiet street, and peaceful at night. This house is an ideal Rock Hall location. This home is well stocked, so most condiments, coffee, tea, sodas and water are included. There are also many toiletry and first aid products. No need to bring soap or shampoo.

Guesthouse in Glen Burnie

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

4.93 out of 5 average rating, 366 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Popular amenities for Chestertown patio rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

5 out of 5 average rating, 7 reviews

A comfortably arranged bedroom features a spacious bed with a light-colored quilt. Natural light enters through multiple windows, complemented by soft curtains. A decorative chair is placed in the corner next to a tall dresser, creating an inviting space.

Apartment in Worton

Country Living 3 Bed Historic Cottage Apartment

Superhost

A cozy living area features a leather sofa accented with patterned cushions. A black coffee table sits on a textured rug, while a flat-screen TV is mounted on the wall. Natural light enters through a window with blinds, illuminating the warm wooden flooring.

Apartment in Federal Hill - Montgomery

4.82 out of 5 average rating, 175 reviews

Charming Federal Hill! One Bedroom With Vibes

4.98 out of 5 average rating, 90 reviews

A well-maintained brick exterior of a home is shown, featuring a front pathway leading to a covered entrance. Lush greenery surrounds the property, and seasonal leaves are scattered across the lawn. A white fence can be seen partially in the background, enhancing the outdoor space.

Apartment in Bel Air

Small town getaway- Bel Air

4.97 out of 5 average rating, 36 reviews

A spacious dock area displays two Adirondack chairs positioned for enjoying the water views. The wooden platform features a vibrant finish, with boats visible in the distance and trees lining the shoreline under a partly cloudy sky.

Apartment in Pasadena

Relaxing Waterfront Apartment!

5 out of 5 average rating, 19 reviews

The exterior of a two-story house, featuring a gray siding facade and a blue metal roof. The front includes a double garage door and a smaller entrance door, both with modern design elements. A gravel driveway is visible in front, surrounded by wooden fencing and greenery.

Apartment in Rock Hall

DragonflyPeake Studio

4.93 out of 5 average rating, 107 reviews

A charming exterior is displayed, featuring a white wooden facade and a welcoming entrance. A brick pathway leads to the door, which is illuminated by a warm light fixture. Decorative greenery frames the doorway, enhancing the home's inviting character.

Apartment in Annapolis

Historic Annapolis Rental Minutes from Downtown

4.96 out of 5 average rating, 26 reviews

A serene sunset is viewed over calm waters, reflecting warm orange and gold hues. Silhouettes of trees and a boat dock are visible in the foreground, with a few boats gently resting on the still water.

Apartment in Dundalk

Waterfront Romantic Studio

5 out of 5 average rating, 17 reviews

A shared front porch features two wooden chairs with light-colored cushions. The porch is shaded by a wooden ceiling and complemented by white columns. The surroundings include greenery, creating a pleasant entrance to the home.

Apartment in Chestertown

114 High Chestertown Lux 1st Floor Apt w/ Patio!

House rentals with a patio

4.99 out of 5 average rating, 108 reviews

A shaded seating area is arranged under a gazebo, featuring a woven outdoor sofa and chairs in warm orange cushions. A central fire pit table complements the setting, surrounded by a patterned outdoor rug on a paved surface, with a fenced backyard visible in the background.

Home in Annapolis

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

4.95 out of 5 average rating, 101 reviews

A cozy living area features a light gray sectional sofa adorned with orange and white throw pillows. A round coffee table sits at the center atop a soft area rug, with a large flat-screen TV mounted on a dark console nearby. Light from recessed ceiling lights brightens the space.

Home in Dundalk

B’more Restful 3 Bedroom 2.5 Bath, Townhouse

4.99 out of 5 average rating, 67 reviews

A modern kitchen features dark wood cabinetry and light-colored countertops. Stainless steel appliances, including a stove and microwave, are visible. An island with two high chairs is illuminated by a stylish light fixture, while sliding glass doors provide access to the outdoor area.

Home in Joppatowne

Two bedroom small ranch with beautiful forest view

4.97 out of 5 average rating, 119 reviews

The lighthouse replica is shown from an elevated angle, surrounded by trees and located beside the water. A wrap-around deck is visible, along with the charming architectural details of the structure and the contrasting red roof.

Home in North East

Red Point Lighthouse

4.91 out of 5 average rating, 43 reviews

A spacious bedroom is illuminated by natural light from a window with light-colored blinds. A large bed with a dark headboard is centered in the room, accompanied by two pillows. Nearby, a floor lamp and a decorative curtain add soft accents to the neutral-toned walls.

Home in Rock Hall

The Blue Jimmy

5 out of 5 average rating, 9 reviews

A welcoming porch is visible, framed by multiple windows allowing natural light to enter. The light yellow exterior contrasts with vibrant flower pots positioned along the steps. Scenic river views are seen in the background, enhancing the peaceful ambiance of the cottage.

Home in Earleville

Delightful 2BR River View Home!

4.91 out of 5 average rating, 11 reviews

The outdoor area features an in-ground pool, accompanied by several sun lounge chairs arranged along the stone patio. Lush greenery surrounds the pool, contributing to a relaxing atmosphere. A staircase leads up to the home, offering easy access between the spaces.

Home in Worton

Cording Lodge*Pool*Pickleball/Basketball court

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

Condo rentals with a patio

5 out of 5 average rating, 29 reviews

A modern kitchen space is highlighted by stainless steel appliances and wooden accents. Two dining chairs are positioned around a wooden table beside a window, providing a view of the exterior. A patterned rug adds warmth to the wooden floor.

Condo in Chestertown

Historic Loft w/ Park View & Spa Access

A serene balcony area is furnished with two wooden chairs and a small table. Lush green foliage provides a natural backdrop, while potted plants add a touch of greenery to the space. A colorful rug is placed beneath the table, enhancing the inviting atmosphere.

Private room in Annapolis

5 out of 5 average rating, 11 reviews

Charming Condo, with Private Bedroom & Bathroom

4.98 out of 5 average rating, 102 reviews

Charming Annapolis Waterfront Condo

An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.

4.97 out of 5 average rating, 68 reviews

Cozy Annapolis Condo

A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.

4.95 out of 5 average rating, 104 reviews

1st Floor Condo in Annapolis

4.92 out of 5 average rating, 86 reviews

A modern studio space is presented, featuring a spacious bed with a dark comforter. A large wall-mounted television is positioned across from the bed, with a wooden media console below it. The kitchenette is equipped with white cabinets and stainless steel appliances, adding a functional element to the inviting layout.

Condo in Mount Vernon

Modern Mt.Vernon studio in great central location

4.9 out of 5 average rating, 42 reviews

A sandy beach stretches along the shoreline, dotted with parasols and beachgoers. Calm waters reflect a clear sky, while a pier juts out in the distance, framed by lush greenery. The serene landscape offers a tranquil view of the surrounding nature.

Condo in Betterton

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

A welcoming living area features a light-colored sofa and an upholstered armchair, positioned around a central wooden coffee table. A unique area rug with intricate patterns adds warmth. The kitchen area, visible in the background, is equipped with modern appliances and a breakfast bar with stools.