Holiday rentals near Old South Country Club
We found 1,566 holiday rentals — enter your dates for availability
If you'd like to stay close to Old South Country Club, take a look at holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Old South Country Club
Showing deals for:1 Aug - 8 Aug
Image gallery for Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
1010 out of 10 rating
Exceptional
(23 reviews)
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
Annapolis, MD
7% off
Price is NZ$24,496
NZ$24,496
NZ$3,499 per night
includes taxes & fees
Image gallery for Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
9.69.6 out of 10 rating
Exceptional
(33 reviews)
Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room
Davidsonville, MD
6% off
Price is NZ$14,680
NZ$14,680
NZ$2,097 per night
includes taxes & fees
Image gallery for Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$10,203
NZ$10,203
NZ$1,458 per night
includes taxes & fees
Image gallery for Spacious luxury rowhouse in the heart of DC. (With lots of plants!)
1010 out of 10 rating
Exceptional
(65 reviews)
Spacious luxury rowhouse in the heart of DC. (With lots of plants!)
Washington, DC
12% off
Price is NZ$6,508
NZ$6,508
NZ$930 per night
includes taxes & fees
Image gallery for Luxury 4 bedrooms each with private full bathrooms Garage Parking
1010 out of 10 rating
Exceptional
(157 reviews)
Luxury 4 bedrooms each with private full bathrooms Garage Parking
Washington, DC
8% off
Price is NZ$11,598
NZ$11,598
NZ$1,657 per night
includes taxes & fees
Image gallery for Escape Villa in Downtown Annapolis
1010 out of 10 rating
Exceptional
(7 reviews)
Escape Villa in Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$7,274
NZ$7,274
NZ$1,039 per night
includes taxes & fees
Image gallery for Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
1010 out of 10 rating
Exceptional
(6 reviews)
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Huntingtown, MD
8% off
Price is NZ$5,722
NZ$5,722
NZ$817 per night
includes taxes & fees
Image gallery for 4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
1010 out of 10 rating
Exceptional
(33 reviews)
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Stevensville, MD
8% off
Price is NZ$11,684
NZ$11,684
NZ$1,669 per night
includes taxes & fees
Image gallery for 3 bedroom home in the heart of historic Capitol Hill
1010 out of 10 rating
Exceptional
(36 reviews)
3 bedroom home in the heart of historic Capitol Hill
Washington, DC
8% off
Price is NZ$6,811
NZ$6,811
NZ$973 per night
includes taxes & fees
Image gallery for Recently Renovated Annapolis Home - Conveniently Located
1010 out of 10 rating
Exceptional
(59 reviews)
Recently Renovated Annapolis Home - Conveniently Located
Annapolis, MD
7% off
Price is NZ$6,939
NZ$6,939
NZ$991 per night
includes taxes & fees
Image gallery for West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
1010 out of 10 rating
Exceptional
(15 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$4,263
NZ$4,263
NZ$609 per night
includes taxes & fees
Image gallery for Classy 2BR Parking Tesla Charger
1010 out of 10 rating
Exceptional
(30 reviews)
Classy 2BR Parking Tesla Charger
Washington, DC
8% off
Price is NZ$5,689
NZ$5,689
NZ$813 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis, MD
8% off
Price is NZ$7,225
NZ$7,225
NZ$1,032 per night
includes taxes & fees
Image gallery for Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
1010 out of 10 rating
Exceptional
(75 reviews)
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Stevensville, MD
8% off
Price is NZ$11,684
NZ$11,684
NZ$1,669 per night
includes taxes & fees
Image gallery for Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,324
NZ$6,324
NZ$903 per night
includes taxes & fees
Image gallery for Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
1010 out of 10 rating
Exceptional
(40 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$9,007
NZ$9,007
NZ$1,287 per night
includes taxes & fees
Image gallery for Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
9.89.8 out of 10 rating
Exceptional
(92 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is NZ$6,001
NZ$6,001
NZ$857 per night
includes taxes & fees
Image gallery for Location Location Location!!!50 Steps from Main Street and all of the action
9.89.8 out of 10 rating
Exceptional
(62 reviews)
Location Location Location!!!50 Steps from Main Street and all of the action
Annapolis, MD
7% off
Price is NZ$5,151
NZ$5,151
NZ$736 per night
includes taxes & fees
Image gallery for Heart of Capitol Hill Row House, Luxury & Location
1010 out of 10 rating
Exceptional
(11 reviews)
Heart of Capitol Hill Row House, Luxury & Location
Washington, District of Columbia
7% off
Price is NZ$6,742
NZ$6,742
NZ$963 per night
includes taxes & fees
Image gallery for Enchanting West River Retreat
1010 out of 10 rating
Exceptional
(8 reviews)
Enchanting West River Retreat
West River, MD
7% off
Price is NZ$5,555
NZ$5,555
NZ$794 per night
includes taxes & fees
Image gallery for Charming 239-year-old former tavern 1 block to water & shops
1010 out of 10 rating
Exceptional
(9 reviews)
Charming 239-year-old former tavern 1 block to water & shops
Annapolis, MD
8% off
Price is NZ$10,002
NZ$10,002
NZ$1,429 per night
includes taxes & fees
Image gallery for Executive luxury for work or play in DC!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Executive luxury for work or play in DC!
Washington, DC
11% off
Price is NZ$3,802
NZ$3,802
NZ$543 per night
includes taxes & fees
Image gallery for "PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
9.89.8 out of 10 rating
Exceptional
(31 reviews)
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
Shady Side, MD
8% off
Price is NZ$7,106
NZ$7,106
NZ$1,015 per night
includes taxes & fees
Image gallery for Urban Sanctuary on Capitol Hill
1010 out of 10 rating
Exceptional
(47 reviews)
Urban Sanctuary on Capitol Hill
Washington, DC
6% off
Price is NZ$2,921
NZ$2,921
NZ$417 per night
includes taxes & fees
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Find the best place to stay - Old South Country Club
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Sleeps 26 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Sleeps 8 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
213 reviews(213 reviews)
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Sleeps 16 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Sleeps 14 · 5 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
87 reviews(87 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value