
Holiday rentals near Old South Country Club
We found 1,614 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:10 Oct - 17 Oct
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
(11 reviews)
Very stylish, family size unit, 2 bed 2.5 bath. Private front yard,unit entrance
Washington, DC
7% off
Price is NZ$2,915
NZ$2,915
NZ$416 per night
includes taxes & fees
Image gallery for Spacious 4 Bedroom Home w/ Hot Tub

9.89.8 out of 10 rating
Exceptional
(17 reviews)
Spacious 4 Bedroom Home w/ Hot Tub
Edgewater, MD
7% off
Price is NZ$9,032
NZ$9,032
NZ$1,290 per night
includes taxes & fees
Image gallery for Executive luxury for work or play in DC!

9.49.4 out of 10 rating
Exceptional
(10 reviews)
Executive luxury for work or play in DC!
Washington, DC
11% off
Price is NZ$5,000
NZ$5,000
NZ$714 per night
includes taxes & fees
Image gallery for 3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!

1010 out of 10 rating
Exceptional
(33 reviews)
3 acre waterfront estate - heated pool, hot tub, yard, pier, game and pub room!
Crownsville, MD
8% off
Price is NZ$40,275
NZ$40,275
NZ$5,754 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 NZ$4,400
NZ$4,400
NZ$629 per night
includes taxes & fees
Image gallery for Rare find! Chic cottage, salt water heated pool May 15-Oct15.

1010 out of 10 rating
Exceptional
(50 reviews)
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Arnold, MD
12% off
Price is NZ$9,757
NZ$9,757
NZ$1,394 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 NZ$3,844
NZ$3,844
NZ$549 per night
includes taxes & fees
Image gallery for Chesapeake Houseboat Getaway on Kent Island, Maryland

9.89.8 out of 10 rating
Exceptional
(33 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville, MD
12% off
Price is NZ$3,554
NZ$3,554
NZ$508 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$11,348
NZ$11,348
NZ$1,621 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
7% off
Price is NZ$13,930
NZ$13,930
NZ$1,990 per night
includes taxes & fees
Image gallery for Guest Quarters at the Inn - 101

9.89.8 out of 10 rating
Exceptional
(12 reviews)
Guest Quarters at the Inn - 101
North Beach, MD
8% off
Price is NZ$2,353
NZ$2,353
NZ$336 per night
includes taxes & fees
Image gallery for Pet-Friendly Cottage – Ideal for Summer Getaways!

1010 out of 10 rating
Exceptional
(6 reviews)
Pet-Friendly Cottage – Ideal for Summer Getaways!
Tilghman, Maryland
11% off
Price is NZ$4,252
NZ$4,252
NZ$607 per night
includes taxes & fees
Image gallery for Annapolis Entertainment Complex

1010 out of 10 rating
Exceptional
(88 reviews)
Annapolis Entertainment Complex
Arnold, MD
8% off
Price is NZ$9,179
NZ$9,179
NZ$1,311 per night
includes taxes & fees
Image gallery for Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi

1010 out of 10 rating
Exceptional
(6 reviews)
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side, MD
8% off
Price is NZ$14,878
NZ$14,878
NZ$2,125 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 NZ$4,876
NZ$4,876
NZ$697 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 NZ$5,871
NZ$5,871
NZ$839 per night
includes taxes & fees
Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!

9.89.8 out of 10 rating
Exceptional
(17 reviews)
Captain's Retreat! Newly Renovated - few steps from the beach!
Annapolis, MD
16% off
Price is NZ$12,586
NZ$12,586
NZ$1,798 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is NZ$11,348
NZ$11,348
NZ$1,621 per night
includes taxes & fees
Image gallery for Quiet Home Close to Downtown Annapolis and Parks

9.69.6 out of 10 rating
Exceptional
(18 reviews)
Quiet Home Close to Downtown Annapolis and Parks
Annapolis, MD
18% off
Price is NZ$5,175
NZ$5,175
NZ$739 per night
includes taxes & fees
Image gallery for Water Views - Close to Downtown Annapolis

1010 out of 10 rating
Exceptional
(44 reviews)
Water Views - Close to Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$6,954
NZ$6,954
NZ$993 per night
includes taxes & fees
Image gallery for Modern Bay Dream

1010 out of 10 rating
Exceptional
(15 reviews)
Modern Bay Dream
Deale, MD
8% off
Price is NZ$6,404
NZ$6,404
NZ$915 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$7,043
NZ$7,043
NZ$1,006 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 NZ$2,029
NZ$2,029
NZ$290 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
(22 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,182
NZ$6,182
NZ$883 per night
includes taxes & fees
Find spaces that suit your style
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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
73 reviews(73 reviews)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Sleeps 18 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
191 reviews(191 reviews)
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Sleeps 16 · 6 bedrooms · 4+ bathrooms
9.29.2 out of 10
Wonderfulwonderful
10 reviews(10 reviews)
Chesapeake Houseboat Getaway on Kent Island, Maryland
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Sleeps 11 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
211 reviews(211 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