Holiday rentals near Old South Country Club
We found 1,677 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:7 Nov - 14 Nov
Image gallery for Very stylish, family size unit, 2 bed 2.5 bath. Private front yard,unit entrance
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Very stylish, family size unit, 2 bed 2.5 bath. Private front yard,unit entrance
Washington, DC
7% off
Price is AU$2,653
AU$2,653
AU$379 per night
includes taxes & fees
Image gallery for Brand New Spacious Luxury Home
1010 out of 10 rating
Exceptional
(8 reviews)
Brand New Spacious Luxury Home
Annapolis, MD
8% off
Price is AU$10,099
AU$10,099
AU$1,443 per night
includes taxes & fees
Image gallery for Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!
1010 out of 10 rating
Exceptional
(10 reviews)
Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!
North Beach, MD
16% off
Price is AU$6,316
AU$6,316
AU$902 per night
includes taxes & fees
Image gallery for Edgewater/Mayo Gateaway w/ Hot Tub
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater, MD
7% off
Price is AU$5,655
AU$5,655
AU$808 per night
includes taxes & fees
Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville, MD
12% off
Price is AU$3,278
AU$3,278
AU$468 per night
includes taxes & fees
Image gallery for Executive luxury for work or play in DC!
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Executive luxury for work or play in DC!
Washington, DC
11% off
Price is AU$3,817
AU$3,817
AU$545 per night
includes taxes & fees
Image gallery for NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.89.8 out of 10 rating
Exceptional
(29 reviews)
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Annapolis, MD
11% off
Price is AU$4,923
AU$4,923
AU$703 per night
includes taxes & fees
Image gallery for HOME AWAY FROM HOME is here for you. Quiet and clean
9.29.2 out of 10 rating
Wonderful
(5 reviews)
HOME AWAY FROM HOME is here for you. Quiet and clean
Washington, DC
8% off
Price is AU$3,499
AU$3,499
AU$500 per night
includes taxes & fees
Image gallery for Unbelievable beach views for 6
1010 out of 10 rating
Exceptional
(8 reviews)
Unbelievable beach views for 6
North Beach, MD
8% off
Price is AU$3,530
AU$3,530
AU$504 per night
includes taxes & fees
Image gallery for Bay views with kayaks, bikes, fire pit, crabbing and more
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side, MD
33% off
Price is AU$3,505
AU$3,505
AU$501 per night
includes taxes & fees
Image gallery for Annapolis Entertainment Complex
1010 out of 10 rating
Exceptional
(90 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is AU$8,277
AU$8,277
AU$1,182 per night
includes taxes & fees
Image gallery for "Point of View" Waterfront cottage with panoramic views on Tilghman Island
1010 out of 10 rating
Exceptional
(11 reviews)
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman, MD
9% off
Price is AU$3,943
AU$3,943
AU$563 per night
includes taxes & fees
Image gallery for Pet-Friendly Cottage – Ideal for Summer Getaways!
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Pet-Friendly Cottage – Ideal for Summer Getaways!
Tilghman, MD
11% off
Price is AU$3,504
AU$3,504
AU$501 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
(95 reviews)
Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!
Edgewater, MD
8% off
Price is AU$5,509
AU$5,509
AU$787 per night
includes taxes & fees
Image gallery for Quiet Relaxing Waterfront Suisse Chalet
9.69.6 out of 10 rating
Exceptional
(76 reviews)
Quiet Relaxing Waterfront Suisse Chalet
Annapolis, MD
11% off
Price is AU$4,575
AU$4,575
AU$654 per night
includes taxes & fees
Image gallery for Blocks to the Boardwalk!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Blocks to the Boardwalk!
North Beach, MD
9% off
Price is AU$1,875
AU$1,875
AU$268 per night
includes taxes & fees
Image gallery for Charming Annapolis WaterVIEW Home
9.69.6 out of 10 rating
Exceptional
(53 reviews)
Charming Annapolis WaterVIEW Home
Annapolis, MD
8% off
Price is AU$6,413
AU$6,413
AU$916 per night
includes taxes & fees
Image gallery for Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
1010 out of 10 rating
Exceptional
(7 reviews)
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
Annapolis, MD
12% off
Price is AU$14,289
AU$14,289
AU$2,041 per night
includes taxes & fees
Image gallery for Modern Bay Dream
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Modern Bay Dream
Deale, MD
8% off
Price is AU$5,929
AU$5,929
AU$847 per night
includes taxes & fees
Image gallery for Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Deale, MD
8% off
Price is AU$2,878
AU$2,878
AU$411 per night
includes taxes & fees
Image gallery for Waterfront Oasis of Annapolis Star
1010 out of 10 rating
Exceptional
(75 reviews)
Waterfront Oasis of Annapolis Star
Annapolis, MD
8% off
Price is AU$3,901
AU$3,901
AU$557 per night
includes taxes & fees
Image gallery for Annapolis waterfront "tiny house" in garden setting
1010 out of 10 rating
Exceptional
(236 reviews)
Annapolis waterfront "tiny house" in garden setting
Annapolis, MD
8% off
Price is AU$1,862
AU$1,862
AU$266 per night
includes taxes & fees
Image gallery for Walking distance to Navy Stadium! No cleaning fees!
1010 out of 10 rating
Exceptional
(5 reviews)
Walking distance to Navy Stadium! No cleaning fees!
Annapolis, MD
8% off
Price is AU$5,619
AU$5,619
AU$803 per night
includes taxes & fees
Image gallery for Sailor's Retreat! Perfect home for the getaway weekend. Best location!
1010 out of 10 rating
Exceptional
(21 reviews)
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Annapolis, MD
8% off
Price is AU$7,422
AU$7,422
AU$1,060 per night
includes taxes & fees
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Find the best place to stay - Old South Country Club
Waterfront Oasis of Annapolis Star
Sleeps 4 · 1 bedroom
1010 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
Waterfront Getaway, Dock Your Boat & Play!
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Floating 2 bed 2 bath condo stunning views of the bay
Sleeps 8 · 2 bedrooms · 2 bathrooms
6.86.8 out of 10
5 reviews(5 reviews)
Circa 1700 Chesapeake Colonial home on the National Register.
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
53 reviews(53 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