Holiday Homes in Maryland

Find and book unique holiday homes on Airbnb

Top-rated Holiday Homes in Maryland

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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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
4.8 out of 5 average rating, 96 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

Top Guest favourite
Holiday home in Oakland
4.97 out of 5 average rating, 135 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 serene beach scene during sunset, showcasing soft waves gently lapping against a sandy shore. The sky is painted in warm hues of orange and pink, reflecting the tranquil waters. Footprints in the sand lead toward the water’s edge, inviting viewers to imagine a peaceful stroll.
Holiday home in Ocean City
4.87 out of 5 average rating, 46 reviews

Luxury Beachfront Home, Family Resort, Great Balc.

Embrace luxury in Ocean City, MD – a beachfront haven offering ocean vistas, 3 pools, sauna, fitness room, secure parking. With 2 bedrooms, 2 baths, a full kitchen, private balcony, and shops/restaurants within walking distance, this sanctuary ensures comfort and convenience. This beachfront gem harmoniously blends luxury, security and convenience, creating an ideal backdrop for your long-awaited beach escape. Don't hesitate – secure your reservation now. Book your dream beach vacation today!

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
4.91 out of 5 average rating, 53 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 sparkling pool is surrounded by a sunlit deck with lounge chairs, inviting relaxation. Lush greenery and trees provide shade, while the two-story condo building is visible in the background under a clear blue sky.
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.

Top Guest favourite
Holiday home in Severna Park
5 out of 5 average rating, 45 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!

Top Guest favourite
Holiday home in Church Creek
5 out of 5 average rating, 13 reviews

Hoopers Island 4BR Waterfront • Sunset Views

This newly built home on Hoopers Island offers you, your family, and friends a cozy, quiet, and peaceful retreat from the hustle and bustle of city life. Enjoy breathtaking sunsets, relaxing backyard campfires, and unforgettable fishing and crabbing experiences on the pier—vacationing doesn’t get any better than this! Friendly smiles and warm waves from the locals will make you feel right at home. Hoopers Island truly is the best little town on the Chesapeake Bay in Maryland!

Guest favourite
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, 70 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.

Top 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, 52 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.

Superhost
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.

Top Guest favourite
A serene waterfront view features calm waters reflecting a sky filled with scattered clouds. The landscape shows lush greenery along the shoreline, while a distant horizon reveals muted colors of land and trees, creating a peaceful natural setting.
Holiday home in Queenstown
4.97 out of 5 average rating, 69 reviews

Heart of the Chesapeake

Enjoy 270 degrees of waterfront living on over 5 acres of land. This one of a kind property is extremely private with a large pool, private sandy beach, (brand new dock 2024 - deep water with shore power and water), pool table, outdoor dining and close to shopping outlets and restaurants. All rooms offer gorgeous views of the Wye River. The fishing is phenomenal and the wildlife is plentiful.

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