Holiday home rentals in Maryland

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Maryland

Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Guest favourite
A two-story home with a light exterior and dark shutters sits against a backdrop of tall trees. A concrete pathway leads to the front steps, which are flanked by two light fixtures. A large grassy area extends around the house, providing a spacious outdoor setting.
Holiday home in Toddville
4.95 out of 5 average rating, 19 reviews

Goose Creek Shore House

Welcome to your unique getaway. Nestled in-between Goose and Tedious creek, this home is surrounded by marsh and woods providing peaceful solitude surrounded by nature. The perfect place to get away from it all an outdoors enthusiasts dream. Enjoy crabbing, fishing, hunting, kayaking, biking, birding and so much more. So many species of birds a birders delight. Short drive to several boat ramps, Fishing bay WMA, Black water refuge. New general store with lots of grocery items minutes away.

A sunny deck features white lounge chairs beside an above-ground pool. Lush greenery lines the background, providing a natural setting. A tall umbrella offers shade, and a potted plant adds a touch of greenery to the space.
Holiday home in Berlin
4.79 out of 5 average rating, 91 reviews

Berlin Beach House, near Ocean City & Assateague!

Close to everything when you stay at this newly renovated vacation home in historic Berlin. Big yard, lots of parking, & walking distance to downtown Berlins restaurants, breweries, grocery, & more. 10 minutes to the beaches of Ocean City Maryland or Assateague Island wild horses. Arcade games and bikes added for 2025 season. Above ground pool open Mid May - Mid Sept. 2 washer & dryers. Locally owned managed and cleaned for a worry free stay. All linens and bath towels provided.License#2023-3

Guest favourite
A view from the entrance showcases a lush green lawn leading to the waterfront. The serene water glimmers in the distance, framed by trees and colorful bushes in the foreground. The porch area features white railings, enhancing the inviting scene.
Holiday home in Piney Point
5 out of 5 average rating, 23 reviews

Family House St. George Island w/Pool. 1.5 hr/DC.

Relax and play at this spectacular waterfront home on 8 acres. Take in the sunset on the large front porch or have a crab feast on the screened in porch. Bring the kids for a sleepover in the huge bunk room - sleeps 8. Three additional bedrooms means there is room for everyone. This property will feel like your own private camp! Heated salt water pool, basketball hoop, bikes, ping pong and foosball tables, other outdoor games and indoor games! Fully equipped kitchen meet all your needs!

Top guest favourite
The exterior of a wooden cabin is framed by tall trees, with warm light glowing from the large front windows. A spacious deck is visible at the entrance, surrounded by lush greenery and natural stone pathways leading through the forest.
Holiday home in Oakland
4.97 out of 5 average rating, 125 reviews

Lakefront Cabin in Stunning Storybook Setting

Reconnect with nature, relax, recharge, & rejuvenate. Our newly updated cabin & incredible setting is just what you need. Lakefront views with boat slip, kayak, hot tub & more. Come enjoy this one of a kind home for fishing (a trout brook runs through our property), bird watching, meteor showers, boating, foliage, horseback riding or skiing (10 mins from Wisp). Within mins you’ll find: hiking, ATV riding, white water raffling, countless farms & restaurants & more. IG page at CampLittleBearMD.

Guest favourite
A welcoming entrance is displayed with double glass doors framed by a stone facade. A cozy seating area features a wicker loveseat adorned with decorative pillows. A 'Welcome' sign stands to the side, complementing the lush green valley visible beyond.
Holiday home in Oakland
4.9 out of 5 average rating, 50 reviews

1-Bedroom near Deep Creek Lake with Mountain View

Renovated in 2022 this spacious 1-bedroom apartment gives a rural Appalachian atmosphere. It has an open floor plan for the kitchen, dining room, and living room, with 2 glass double doors leading to the patio in the front. for a great view of the valley from inside and outside. It has a full kitchen, for all your cooking needs and Parking for up to 2 cars. (Note to guest booking longer than 1 week. The cleaning fee is $120, so the additional $40 will be requested of you after you book.)

Top guest favourite
A cozy living room features a dark sectional sofa adorned with colorful throw pillows. A flat-screen television is placed on a dark media console. Natural light enters through the sliding glass door, which leads to an outdoor deck. A potted plant adds a touch of greenery.
Holiday home in Ocean City
4.95 out of 5 average rating, 44 reviews

Bayside Breeze in North Ocean City!

Relax and enjoy all that North Ocean City has to offer! This family friendly 2-level condo has everything you need for a relaxing getaway. Spend the day swimming in the pool or bring the boat and take advantage of this home's exclusive boat slip! Local amenities all within walking distance include tennis & basketball courts, a playground, restaurants, bars, Acme grocery store, and of course the beach! Sorry, no high school seniors. Non- family group tenants must be 25 years or older.

Two adirondack chairs, one green and one red, are positioned on a grassy area overlooking a calm body of water. Trees frame the scene, offering a sense of privacy. The sky is dimmed, suggesting early evening light.
Holiday home in North East
4.92 out of 5 average rating, 71 reviews

Bonfire by the Creek

Relax in this cozy little home by the creek; fully furnished, beds freshly made; plenty of pillows & blankets, two TV's, and a fully-equipped kitchen. Be sure to take one of our kayaks out to explore the cove & creeks along the Elk River, then cookout on our propane grill & enjoy your dinner by the creek watching the wildlife- Eagles, Osprey, Heron, Ducks, Geese, & maybe even deer or a fox walking along the shoreline. After dinner, a bonfire is a great way to enjoy the evening!

Top guest favourite
A charming waterfront home is set amidst lush greenery, featuring a welcoming porch and a two-car garage. Vibrant foliage surrounds the property, while soft sunlight filters through the trees, highlighting the serene landscape.
Holiday home in Severna Park
5 out of 5 average rating, 40 reviews

Waterfront 5 Bedroom Home Close to Annapolis

Beautiful waterfront 5 bedroom home located off of the Magothy River. Close proximity to many shops & restaurants, downtown Annapolis, the Naval Academy & a short drive from BWI. This home was recently renovated and offers a lot of room to host a weekend away with your family or friends. Enjoy the beautiful sunsets from the private pier and almost 1 acre of land. Feel free to use the kayaks, canoes, & stand up paddleboards to explore the breathtaking views of the Magothy River!

Superhost
The living room area features a comfortable gray couch complemented by decorative pillows. A glass coffee table sits in front, accompanied by a green floral chair and an upholstered footstool. The space is well-lit, showcasing an open design that connects to the dining area.
Holiday home in Takoma Park
4.91 out of 5 average rating, 66 reviews

Spacious Garden Apartment on Delightful Street

This delightful apartment is on the ground floor of a large single family house in a charming neighborhood, just 2 blocks from the center of Takoma Park, a 15 minute walk to the Metro. With its open floor plan, you will enjoy the large living room and windowed alcove, a fully-equipped kitchen, dining room and ample-sized bedroom with wall-to-wall closets. There is a separate entrance and laundry room. The house has a large front yard, with shade trees and nice gardens.

Guest favourite
The exterior of a two-story garage apartment is shown, featuring beige siding and contrasting dark shutters. A distinctive teal sign is mounted above the entrance, while two white garage doors are visible at the base. A tree with green leaves is partially displayed on the right.
Holiday home in Ocean City
4.98 out of 5 average rating, 46 reviews

Vacay Stay-2BR/1Bath, Family Groups Only

Family friendly upstairs, garage apartment. Located on the same property as Dolores by the Sea, only 0.2 miles away from beach and boardwalk. Nestled in a quiet part of town but close to everything. This quaint apartment is perfect for small family’s looking for a relaxing beach vacation. Due to neighborhood restrictions we can only rent to family groups or individuals 25 y/o and over. This is a upstairs unit and may not be for those who have mobility restrictions.

Guest favourite
A comfortable bedroom features a spacious bed with floral bedding, complemented by three framed botanical prints on the wall. A cozy chair is positioned next to the bed, and a light rug creates a soft contrast against the wood-like flooring.
Holiday home in Rockville
4.95 out of 5 average rating, 110 reviews

One Bedroom Guest Studio Suite

Come stay at our newly renovated guest suite in the heart of Rockville, MD. The 1-bedroom studio suite is fully furnished with a fully equipped kitchenette and bathroom. Our suite is steps away from public transportation (Route 48) which takes you to the red-line metro (Wheaton or Rockville), and a walkable distance from a shopping center featuring a grocery store, restaurants, etc. There is ample space for parking in front of the property.

Guest favourite
The historic log cabin is framed by tall trees, showcasing a blend of natural wood and painted siding. A prominent chimney rises from the roof, and a covered porch extends around the front, inviting relaxation in a serene setting.
Holiday home in Thurmont
4.93 out of 5 average rating, 199 reviews

"Breeches Pocket" C.Wr Log Cabin/House Getburg-DC

This Historic 4BR log Cabin (house) on "Saint Elizabeth" farm is a true gem. It is minutes from hiking and biking trails, ski resorts, history tours, and the Catoctin Mountains. It has exceptional architectural details and a gorgeous interior design. We have rented it for 14 years and maintain it at the highest level. We guarantee you will be thrilled with your stay. READ "show more" (below) to understand the layout of this house.

Popular amenities for holiday home rentals in Maryland

Destinations to explore