Villa holiday rentals in Maryland

Westmore Estate II Contemporary Cave Gorgeous B&B

Immaculate bedroom close to an oval king bedroom on 1st floor of a large, architect-designed home on 6 private landscaped acres. The bathroom, renovated in 2019, may be shared on rare occasions. There is lots of light despite there being no real window (there is a large faux window with remote-controlled LED lighting)! Coffee served from 7:30-9:00 AM except for extended stay guests. $50,000 renovation of patio, pool, tennis court & fire bowl. Security cameras at entrances. Staircases in & out.

Location · View · Outdoor spaces

Lakeview/Golf course front home - 4 Bed/3 baths

Golfer's paradise on River Run golf course in Berlin, MD! 8 miles to Ocean City! Located overlooking a lake on the 4th hole in the River Run Golf Community. This well decorated duplex is in an ideal location. The beaches, amusements, restaurants, casino, movies, and shopping outlets are all within 15 minutes. You can enjoy the pool, tennis & golf on site in the River Run community. This duplex has 4 BDRM's & 3 full baths. The maximum occupancy allowed for this rental is eight people. NO PETS.

Family · Location · Beach

Close to DC Excellent location.

Close to Washington, DC. Entire House 4 bedrooms with full kitchen, 3 Full bath, 1 half bathrooms, living and dining area. The family room has 60 60-inch TV. Free 2 parking spaces. Free high-speed net. Work Space with 2 writing Desks. Master bedroom with a king bed and seating area. 2 Roku Smart TV in the family room. Fully equipped New kitchen ready for you. Washer and dryer in the lower level. Basement has a large suite with a queen bed setting and dining area, and .60 TV. Full bath

Location · Family · Condition

Cozy Bedroom Free WiFi &parking At VILLA DE BOWIE

This luxurious house recently fully renovated new kitchen and bathrooms with new Hvac system and new furniture and new bedrooms. open concept kitchen with 2 living rooms and library, watch the sunset in the backyard and enjoy the sun rises in the front yard, quiet neighborhood and relaxing, no traffic in the neighborhood, close by the bowie state university, close by the town center. 20 minutes from Washington DC and Annapolis,closed by the airports and major roads 197, 50 ,495 ,450 ,95 ,295

Cleanliness · Accuracy · Indoor spaces

Deer Haven at Bacon Hall

Fully unwind in style at this pet friendly two-story modern villa. Nestled in the quiet country of Sparks Glencoe, Maryland you'll have ample space to stretch out and enjoy the numerous amenities. From leather furniture, unique lighting fixtures, and marble counters, to a show-stopping spiral staircase and spacious back deck, you'll be grateful you didn't opt for a hotel (and its inevitable noisy neighbors). Enjoy the separate game room with a pool table and arcade during warmer months!

Value · Family · Comfort

Private Peninsula Estate, Pool Houses, Crab Shack

This isn't a typical waterfront rental. Durham-Hythe Estate is a private 7.5-acre peninsula compound with over 750 feet of shoreline; designed for groups who want space, privacy, and a true Eastern Shore experience. Grab a cup of coffee or tea and watch the sunrise on the dock! Enjoy Chef-prepared meals while watching the evening sunset. Estate living includes swimming, spa time, cookouts, playing with your dogs in the 4-acre field, crab feasts, and relaxing in the raised rose garden!

Value · Family · Access

Bay Access 3 bedroom Main House in Franklin Manor

Escape to a beautifully renovated coastal cottage with stunning bay views and unforgettable sunsets, just 20 minutes from Annapolis. Located in a quiet waterfront community, this home offers the perfect blend of relaxation, outdoor adventure, and comfortable living. Enjoy access to two private beaches, fishing piers, a swim platform, playground, baseball field, volleyball court, picnic pavilion, and a mile-long bayfront park—all just steps from your door.

Quiet · Cleanliness · Parks

Spacious and Beautiful Home with "Hygge"!

Make memories to last a lifetime in a home that marries luxury with a serene ambiance that embraces the Scandinavian Hygge style. Enchanting and elegant, but far from fussy, our home makes the ideal spot for friends and family marking a special occasion. Gather by the fire, play a game of pool, or unwind in the hot tub. Note: this is our home, there will be personal items in the house, but we do make an effort to clear as much as possible away.

Family · Location · Backyard

Luxe Homey Get-Away Beach Cove

Quiet and Private Spacious home, our guest have the privacy of a full kitchen, three large bedrooms, a large living room with a fire place as well as an outdoor patio perfect for Cookouts or Smores. This secluded home is only 10 minutes away from the Beach and is a perfect Family Get-Away from Home! We are very accommodating host so if you have any questions about pricing, dates and availabilities or amenities please contact us at any time.

Family · Value · Beach

5BR Sleeps 14, Hot Tub, Pool table, 5 Min to Lake

Timber Ridge Haven is officially an Airbnb 'Guest Favorite'! We owe this milestone to our wonderful guests and look forward to providing you with the same high-quality, comfortable mountain experience. This spacious 5-bedroom chalet features stunning, direct views of the Wisp Resort ski slopes and is just steps from lake access. Perfect for family reunions or ski trips, our home sleeps 14 and features a private hot tub and arcade.

Location · Air conditioning · Cleanliness

Cheery & Cozy Beach Villa - Walk to Beach

This Villa Offers All The Items You Want For A Perfect Vacation! Beautiful Spacious 3 BR 2 Bath With Sleep Sofa To Sleep Up To 8 Comfortably. Master BR Has A King Bed With A Private Bath. BR 2 has A Queen Bed and BR 3 Has Twin Bunk Bed. Both Have Windows Facing The Coastal Hwy. The Second Full Bathroom Is In The Hallway. Located At 90th St It Is Convenient To A Supermarket And Within Walking Distance To Popular Restaurants.

Value · Location · Parking

River Run Retreat | Pool + Golf Escape

Sun-filled River Run retreat near beaches with pool, golf, tennis & more! Enjoy a private deck, sunroom, fireplace, and spacious living area with central AC and WiFi. Fully equipped kitchen, king + queen beds, W/D, and all linens included. Relax by the pool, grill on the patio, or explore nearby Ocean City, fishing, and attractions. Perfect for families or friends seeking a coastal getaway in a peaceful golf community.