Stayifyoudare - Vacation Rentals in Old South Country Club

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From $259

         

9.8 (97 Reviews)

House

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Deale

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From $646

         

|

10.0 (1 Review)

House

New! Pool Vibes At Vanishing Run

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Harwood

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From $102

         

10.0 (33 Reviews)

House

134 m² House ∙ 1 bedroom ∙ 2 guests

• 1442 ft² House
• Air Conditioner
• Parking
• TV

• Maryland
• Lothian

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From $276

         

9.4 (440 Reviews)

Hotel

Anchored Inn at Hidden Harbour Marina

• Air Conditioner
• Parking
• Pool

• Maryland
• Deale

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From $124

         

10.0 (23 Reviews)

House

Secluded Lothian Farmhouse on 45 Acres w/Fire Pit

• Air Conditioner
• Parking
• TV

• Maryland
• Lothian

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From $167

         

|

8.9 (9 Reviews)

House

Exquisite 1 Bedroom, 1 Full Bath Apartment

• Air Conditioner
• Parking
• View

• Waldorf
• Upper Marlboro

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From $136

         

New

Resort

Private room ∙ 2 guests

• Air Conditioner

• Waldorf
• Upper Marlboro

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From $116

         

7.2 (538 Reviews)

Hotel

Executive Inn And Suites

• Air Conditioner
• Parking
• TV

• Waldorf
• Upper Marlboro

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From $522

         

8.6 (4 Reviews)

House

Vanishing Run Retreat with Pool

• Air Conditioner
• Pet Friendly
• TV

• Maryland
• Harwood

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From $136

         

|

New

House

Secluded Lothian Farmhouse on 45 Acres with Fire Pit

• Parking
• View
• Accessibility

• Maryland
• Lothian

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From $874

         

New

House

Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Deale

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From $75

         

New

Apartment

Guest Favorite

• Air Conditioner
• Parking
• Security/Safety

• Waldorf
• Upper Marlboro

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From $622

         

New

House

Marlboro Mansion - Located on over 2 Acres in Upper Marlboro, MD

• Air Conditioner
• Pet Friendly
• Security/Safety

• Waldorf
• Upper Marlboro

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From $269

         

|

9.1 (273 Reviews)

Hotel

Anchored Inn at Hidden Harbor

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Deale

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From $270

         

New

House

25+ walk friendly acres

• Air Conditioner
• Pet Friendly
• TV

• Waldorf
• Upper Marlboro

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From $115

         

7.0 (118 Reviews)

Hotel

Executive Inn & Suites Upper Marlboro

• Air Conditioner
• Parking
• Pet Friendly

• Waldorf
• Upper Marlboro

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From $185

         

New

Apartment

Exquisite & Cozy 1-bedroom apartment with WiFi, AC in lovely Upper Marlboro

• Air Conditioner
• Parking
• TV

• Waldorf
• Upper Marlboro

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From $926

         

10.0 (80 Reviews)

House

Spacious Luxury 6 BR Home, Sleeps 16, Private Pool, In Nature, Convenient to DC

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Galesville

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From $532

         

9.8 (18 Reviews)

House

Modern Bay Dream

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Deale

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From $245

         

9.0 (10 Reviews)

House

Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.

• Air Conditioner
• Parking
• Balcony/Terrace

• Maryland
• West River

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From $165

         

2.0 (1 Review)

Condo

Cozy 2-bedroom condo in welcoming Upper Marlboro with AC, WiFi.

• Air Conditioner
• Parking
• Security/Safety

• Waldorf
• Upper Marlboro

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From $1,500

         

New

House

Private Pool Paradise Modest Socials Welcomed

• Air Conditioner
• Parking
• Pool

• Maryland
• Lothian

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From $998

         

New

House

42 Acres of Serenity & Nature Just15 Miles To Annapolis

• Air Conditioner
• Parking
• Pool

• Maryland
• Croom

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From $428

         

10.0 (1 Review)

Other

Historic Farmhouse 30 minutes to DC/Annapolis. 4BR Large and Inviting, Zipline

• Air Conditioner
• Parking
• TV

• Maryland
• Croom

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Old South Country Club.