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The Winchester HotelvsGrand Daddy Hotel

Both hotels are rated highly by travel writers. Overall, Grand Daddy Hotel ranks slightly higher than Winchester Mansions. Grand Daddy Hotel is ranked #10 in Cape Town with positive reviews from 9 sources like Travel + Leisure, Lonely Planet and On the Grid.

The Winchester Hotel
8/10
221 Beach Road, Sea Point, Cape Town Central 8005, South Africa
From $120/night
  • Bar/Lounge
  • Free Internet
  • Room Service
  • Free Breakfast
  • Shuttle Bus
  • Laundry Service
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Frommer's Frommer's
"Still family owned, the hotel is distinguished by its friendly service." Full review
i
The best "classic" rooms marry modern design with old-fashioned charm (a few antiques, floral artworks) -- ask for no. 306.
Lonely Planet Lonely Planet
Top choice
"The Winchester offers a seaside location... old-fashioned style and some corridors lined with putting greens for a spot of golf practice." Full review
DK Eyewitness DK Eyewitness
"A renowned, privately owned four-star hotel on Sea Point’s coastal boulevard. Tailor-made tours to the Winelands or to Cape Point can be arranged through consultation with the management."
Rough Guide Rough Guide
"A self-consciously colonial-style 1920s hotel, in a prime spot across the road from the seashore, with an atmosphere straight from the pages of Agatha Christie."
Time Out Time Out
"This charming property combines old world details with a thoroughly modern understanding of what one wants from a hotel stay." Full review
The Telegraph The Telegraph
8.0
"The grande dame of the Atlantic Seaboard, a three-storey gabled hotel enjoying an ideal location on the ocean-hugging Sea Point pedestrian promenade and offering the best-value sea views in the city." Full review
Travel + Leisure Travel + Leisure
"Situated on the Sea Point Promenade, this Cape Dutch—style hotel faces the Atlantic on one side and Table Mountain on the other." Full review
Fodor's Fodor's
"This seafront hotel scores high with travelers for good value for money." Full review
Grand Daddy Hotel
8/10
38 Long Street, Cape Town Central 8000, South Africa
From $46/night
  • Bar/Lounge
  • Free Internet
  • Room Service
  • Laundry Service
  • Concierge
  • Laundy Room
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Frommer's Frommer's
"A relatively high level of luxury and a strong buzz make this one of the liveliest hotels in town." Full review
Fodor's Fodor's
"This is a stylish inner-city, glamorous spot that's also good value for travelers."
i
Ask for a corner room, which has three large windows.
Rough Guide Rough Guide
"Seven retrocool American Airstream trailers, decorated by local artists, sit on the roof of the Grand Daddy Hotel, linked by wooden walkways greened by indigenous plants."
Time Out Time Out
"Following in the footsteps of its quirky predecessors Daddy Long Legs Boutique Hotel and Daddy Long Legs Self Catering Apartments, this plush hotel offers top-notch accommodation with a twist." Full review
Star Service Star Service
"Occupying a charming low-rise historic building on a bustling corner of Long Street, this quaint lodging is packed with plenty of spunk." Full review
i
The hotel's main showpiece is the seven, silver Airstream trailers perched on the roof where guests can choose to stay.
Afar Magazine Afar Magazine
"One of the city’s quirkier havens, though it somehow manages to walk the fine line between campy and classy." Full review
On the Grid On the Grid
"Legendary, luxurious and with a stylish eatery, The Grand Daddy is original and quintessentially Cape Town." Full review
Travel + Leisure Travel + Leisure
"The 26 standard guest rooms are more classic, although they do incorporate South African motifs like aloe-print headboards. " Full review
The Telegraph The Telegraph
7.0
"Boutique hotel has a young, funky character that will suit those wanting an urban central-city base, close to the Long Street’s action and Bree Street’s hip restaurants and bars." Full review
Lonely Planet Lonely Planet
Top choice
"The Grand Daddy’s star attraction is its rooftop 'trailer park' of penthouse suites, made from seven vintage, artistically renovated Airstream trailers. The hotel's regular rooms are also stylish" Full review
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