Holiday rentals near Old South Country Club
We found 1,572 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:8 Aug - 15 Aug
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$14,276
NZ$14,276
NZ$2,039 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$11,701
NZ$11,701
NZ$1,672 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
(69 reviews)
Spacious luxury rowhouse in the heart of DC. (With lots of plants!)
Washington, DC
12% off
Price is NZ$6,565
NZ$6,565
NZ$938 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$5,773
NZ$5,773
NZ$825 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$7,699
NZ$7,699
NZ$1,100 per night
includes taxes & fees
Image gallery for Recently Renovated Annapolis Home - Conveniently Located
1010 out of 10 rating
Exceptional
(60 reviews)
Recently Renovated Annapolis Home - Conveniently Located
Annapolis, MD
8% off
Price is NZ$8,858
NZ$8,858
NZ$1,265 per night
includes taxes & fees
Image gallery for 3 bedroom home in the heart of historic Capitol Hill
1010 out of 10 rating
Exceptional
(37 reviews)
3 bedroom home in the heart of historic Capitol Hill
Washington, DC
8% off
Price is NZ$6,510
NZ$6,510
NZ$930 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$11,526
NZ$11,526
NZ$1,647 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$4,472
NZ$4,472
NZ$639 per night
includes taxes & fees
Image gallery for Classy 2BR Parking Tesla Charger
1010 out of 10 rating
Exceptional
(31 reviews)
Classy 2BR Parking Tesla Charger
Washington, DC
7% off
Price is NZ$4,846
NZ$4,846
NZ$692 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$7,154
NZ$7,154
NZ$1,022 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$11,526
NZ$11,526
NZ$1,647 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$5,919
NZ$5,919
NZ$846 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$5,963
NZ$5,963
NZ$852 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
(41 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$9,285
NZ$9,285
NZ$1,326 per night
includes taxes & fees
Image gallery for Urban Sanctuary on Capitol Hill
1010 out of 10 rating
Exceptional
(50 reviews)
Urban Sanctuary on Capitol Hill
Washington, DC
6% off
Price is NZ$2,947
NZ$2,947
NZ$421 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$9,912
NZ$9,912
NZ$1,416 per night
includes taxes & fees
Image gallery for Unwind in Tranquility: Blocks from Capitol Hill and H Street Corridor Retreat
1010 out of 10 rating
Exceptional
(10 reviews)
Unwind in Tranquility: Blocks from Capitol Hill and H Street Corridor Retreat
Washington, DC
5% off
Price is NZ$5,296
NZ$5,296
NZ$757 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$3,856
NZ$3,856
NZ$551 per night
includes taxes & fees
Image gallery for H St. DC Haven / 4-BR Homestay
8.88.8 out of 10 rating
Excellent
(16 reviews)
H St. DC Haven / 4-BR Homestay
Washington, District of Columbia
7% off
Price is NZ$5,257
NZ$5,257
NZ$751 per night
includes taxes & fees
Image gallery for Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
9.29.2 out of 10 rating
Wonderful
(34 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Annapolis, MD
8% off
Price is NZ$2,642
NZ$2,642
NZ$377 per night
includes taxes & fees
Image gallery for Stunning Home on Capitol Hill
1010 out of 10 rating
Exceptional
(53 reviews)
Stunning Home on Capitol Hill
Washington, DC
8% off
Price is NZ$5,946
NZ$5,946
NZ$849 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(27 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$12,402
NZ$12,402
NZ$1,772 per night
includes taxes & fees
Image gallery for Gorgeous 1BR apt/Capitol Hill/Eastern Market Entire rental unit in Washington
1010 out of 10 rating
Exceptional
(6 reviews)
Gorgeous 1BR apt/Capitol Hill/Eastern Market Entire rental unit in Washington
Washington, DC
7% off
Price is NZ$2,150
NZ$2,150
NZ$307 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
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 20 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
186 reviews(186 reviews)
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Sleeps 16 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 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
215 reviews(215 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