Holiday rentals with a patio in Rock Hall

4.96 out of 5 average rating, 157 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, 113 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

4.93 out of 5 average rating, 114 reviews

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

4.96 out of 5 average rating, 112 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.

Home in Stevensville

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 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.

4.98 out of 5 average rating, 169 reviews

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.

5 out of 5 average rating, 135 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!

4.97 out of 5 average rating, 124 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.

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.

5 out of 5 average rating, 117 reviews

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.

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, 174 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, 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, 256 reviews

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

A bright living space is characterized by light blue walls and hardwood flooring. A brown recliner and a wooden coffee table are present, along with a turquoise entertainment unit housing a television. Natural light fills the room through multiple windows, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 113 reviews

2 Beds, 2.5 Baths - Perfect Downtown Location

Charming and inviting, this beautifully updated home in historic Chestertown offers the perfect blend of comfort and location. Featuring 2 bedrooms—each with its own en suite bath—plus an additional half bath on the first floor, it comfortably accommodates up to 4 adults. Enjoy bright, thoughtfully designed living spaces throughout. Just a few blocks from downtown shops, restaurants, and waterfront, and an easy walk to Washington College.

Place to stay 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, 385 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 Rock Hall Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.96 out of 5 average rating, 198 reviews

A light-filled living space features a large, plush sectional sofa adorned with decorative pillows. A round coffee table sits at the center, surrounded by a tasteful area rug. A small dining area is visible, with a wooden table and chairs, and greenery is provided by a nearby potted plant.

Apartment in Washington

Subway & Easy Parking! Sunny 2 Bdrm w/ King Bed

Apartment in Upper Marlboro

4.94 out of 5 average rating, 192 reviews

Kone Oasis- hot tub, pool, theater/game rm.

Apartment in Federal Hill - Montgomery

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.

4.83 out of 5 average rating, 183 reviews

Charming Federal Hill! One Bedroom With Vibes

Apartment in Mt. Washington

A two-story house is set against a backdrop of clear blue sky and lush greenery. A spacious deck is visible at the back, featuring a vibrant red umbrella. Well-maintained grass surrounds the home, punctuated by several trees for added privacy.

4.95 out of 5 average rating, 122 reviews

Mother-in-law suite with yard

4.97 out of 5 average rating, 107 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

4.93 out of 5 average rating, 110 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

4.98 out of 5 average rating, 40 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

Superhost

The exterior of a two-story beach house is shown, featuring white siding and dark shutters. A welcoming front porch is visible, adorned with a small American flag. A pathway leads through green grass to the entrance, surrounded by landscaped shrubs.

Apartment in North Beach

4.89 out of 5 average rating, 100 reviews

Spacious Beach House Top Floors - Walk Everywhere!

Holiday House Rentals with a Verandah

The exterior features a welcoming entrance with a wooden deck, adorned with turquoise chairs for relaxation. Lush greenery and blooming flowers enhance the vibrant atmosphere. The entrance is framed by a mix of brick and light-colored siding, providing a charming and friendly appearance.

4.98 out of 5 average rating, 46 reviews

The Bay House - just a few steps to the bay!

A serene beach scene captures a vibrant sunset, with warm colors reflecting over the calm water. The sandy shore leads to gentle waves, while silhouettes of trees and a distant pier add depth to the peaceful landscape.

5 out of 5 average rating, 20 reviews

Bay Beach Oasis

5 out of 5 average rating, 107 reviews

A spacious living area, featuring a small sectional couch facing a TV mounted on the wall. A foosball table occupies the foreground, while a dining nook with a round table and chairs is visible in the background. Soft artificial lighting enhances the relaxed setting.

Home in Crownsville

"Hilltop Hideaway"- Private basement suite

4.96 out of 5 average rating, 127 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

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.

4.91 out of 5 average rating, 46 reviews

The Blue Jimmy

5 out of 5 average rating, 41 reviews

1-Particular Harbor: A Coastal Oasis!

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.

4.97 out of 5 average rating, 67 reviews

High Tide & Hound

A well-appointed bedroom features a spacious bed dressed in blue linens, complemented by decorative pillows. A cozy throw rests at the foot of the bed. A mounted artwork depicting a ship on the water is visible above the headboard, and soft lighting is provided by a bedside lamp.

5 out of 5 average rating, 90 reviews

Lovely Home in Chestertown With Free EV Charging

Holiday condos with a patio

5 out of 5 average rating, 34 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

4.88 out of 5 average rating, 112 reviews

A modern kitchen showcases a marble-topped island with bar seating for three. Natural light illuminates the space, highlighting the wooden stools and kitchen essentials arranged on the shelves. A potted plant in the foreground adds a touch of greenery, enhancing the inviting decor.

Condo in Ellicott City

Historic Schoolhouse Condo

4.97 out of 5 average rating, 69 reviews

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.

Condo in Annapolis

Cozy Annapolis Condo

4.95 out of 5 average rating, 132 reviews

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.

Condo in Annapolis

1st Floor Condo in Annapolis

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!

4.9 out of 5 average rating, 83 reviews

A modern kitchen features dark cabinetry and a large island with granite countertops. Stainless steel appliances are integrated, and warm lighting illuminates the space. Seating for four is provided at the island, creating a cozy dining area. A staircase with wooden railings leads to the upper level.

Condo in Hanover

Parkside Retreat Brand New 3-bedroom condo

4.96 out of 5 average rating, 113 reviews

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.

Condo in Annapolis

Funky Uptown Apt meets Downtown - Hist District