Holiday Homes in Maryland

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

Location · Value · Biking

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!

Location · Family · View

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.

Value · Location · Barbecue

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!

Value · Location · Laundry

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.)

Value · Location · TV

Knit Inn

Attached to a yarn store, this place is a crafters dream come true. Located on Main St in the utterly charming town of Frostburg, MD our spot will give you access to all of the best parts of Frostburg. With four separate bedrooms encompassing 7 beds, this massive property sleeps 13; added to that are two kitchens, two full bathrooms, and plenty of living space. We've designed this as an escape, perfectly curated to allow you the ample crafting time you've been missing in your daily life.

Family · Location · Hospitality

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.

Location · Family · Checkout

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!

Value · Location · Hiking

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!

Family · Location · Comfort

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!

Value · Location · Cleanliness

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.

Value · Family · Sleep quality

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.

Location · Family · Biking