Windermere Vacations from $423

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Your Windermere Vacation

The best way to experience this vibrant city is with a customized Windermere vacation package. Stay in the neighborhood of De Waterkant, which is great for cafes, nightlife and shopping or go someplace else — our package deals are all about you. You'll want to do some exploring during your trip to Windermere. Carve out some time for big-name attractions such as University of Cape Town, GrandWest Casino & Entertainment World and Grand West. Stop daydreaming and start doing. Explore the multitude of options on Expedia today and finally put your Windermere vacation plans in motion!

The Latest Windermere Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Point B Guest House

Green Point

$423

per person

Dec 9 - Dec 12

just found

Roundtrip flight included

Johannesburg (JNB) to Cape Town (CPT)

9/10 Wonderful! (17 reviews)

Gem in Cape Town will definitely stay again - extremely helpfull staff and amazing hospitality

Reviewed on Aug 15, 2026

Blackbrick Hotel Gardens - Cape Town

Cape Town City Centre

$489

per person

Dec 9 - Dec 12

just found

Roundtrip flight included

Johannesburg (JNB) to Cape Town (CPT)

10/10 Exceptional! (1 review)

book this hotel for my staff and they only have great things to say

Reviewed on Sep 10, 2026

The Bantry Bay Aparthotel by Totalstay

Sea Point

$493

per person

Dec 9 - Dec 12

just found

Roundtrip flight included

Johannesburg (JNB) to Cape Town (CPT)

8.8/10 Excellent! (344 reviews)

The aparthotel is located 1 street back from the beach, its close to the main street with shops, bars, cafes, restaurants. The area is safe and quiet. Its easy to walk to places like beach and shops. My check in was quick and easy and my queries were answered quickly and fully. I had a nice friendly welcome. The room (Penthouse) is large, plenty of space, the views are fantastic - ocean to front, mountain to rear. The kitchen has a hob and microwave and a fridge. I did self-catering and it worked great. The living area is lovely, comfortable, great view. The extra bonus is my room had a patio to the rear! The bedroom is spacious, airy, lovely view, big bed. Big bathroom with walk in shower and a proper bath tub and plenty of space. I slept very well! The apartment is cleaned regularly and they change towels and bedding too. There is a small outdoor pool, a bar and there is onsite restaurant for breakfast & lunch. Parking is onsite and secure, I had a VW Polo and this fitted fine, some of the spaces would be tight for a large car or a full size SUV. This is a great location for a nice quiet base for exploring and for relaxing....

Reviewed on Sep 21, 2026

The Tree House Boutique Hotel

Cape Town City Centre

$694

per person

Dec 9 - Dec 12

just found

Roundtrip flight included

Johannesburg (JNB) to Cape Town (CPT)

9.6/10 Exceptional! (242 reviews)

If staying in Cape Town, I would highly recommend staying at the Tree House. The rooms are modern and clean, the breakfast is great. However, the real value of this hotel is the staff. You could not ask for a kinder group of people. From the moment you arrive to the time you need to check out, the staff are always checking if there is anything they can help with, or any places they can recommend. That type of atmosphere is very hard to capture and this team do it seamlessly. 100% will return if I am ever in Cape Town.

Reviewed on Jul 24, 2026

POD Camps Bay

Camps Bay

Save 100% on your flight

$3,369

per person

Nov 25 - Dec 1

found 10 hours ago

Roundtrip non-stop flight included

New York (NYC) to Cape Town (CPT)

9.8/10 Exceptional! (232 reviews)

Where to stay in Windermere

Find the best Windermere areas and neighborhoods for the activities you enjoy most. Learn more about Windermere

A marina with boats docked, a large building with a sign reading "Spirit of Victoria," and a wooden dock with a 'Please Keep' sign.

Victoria and Alfred Waterfront

Explore the oldest working harbour in the Southern Hemisphere, offering shopping, dining, and attractions like Battery Park, the 1882 clock tower, and Zeitz MOCAA contemporary art museum.

A coastal town with rocky shores, a beach, and mountains in the background.

Camps Bay

1 out of top 10 points of interest in this area

Affluent suburb with a picturesque bay, Camps Bay offers a variety of beaches, including the popular Camps Bay Beach and Glen Beach for surfing. Explore the open-air curio market at Koeël Bay and enjoy picnics at Oudekraal, all near hotels, restaurants, and shops.

A coastal promenade with a beach, a dog, and a runner.

Sea Point

Bring the kids to the playgrounds and cafés in this dynamic, rejuvenated coastal area in the shadow of a mossy mountain.

A multi-story building with a green facade and white trim, labeled "TYNE BUILDINGS."

Cape Town City Centre

2 out of top 10 points of interest in this area

Known for its majestic mountain landscape and popular shops, there's plenty to explore in Cape Town City Centre. Check out top attractions like Castle of Good Hope and South African National Gallery, and jump on the metro at Woodstock Station or Esplanade Station to see more of the city.

A stadium with a circular roof and a brick facade.

Green Point

1 out of top 10 points of interest in this area

Travelers like the cocktail bars in Green Point, and Greenpoint Market is a top attraction you might want to visit.

Windermere Hotel Deals

Taj Cape Town

1 Wale Street Cape Town Western Cape

Fully refundableReserve now, pay when you stay

$172 nightly

$198 total

Sep 23 - Sep 24

Total with taxes and fees

9.6/10 Exceptional! (1,006 reviews)

"Great value and quality"

Reviewed on Sep 21, 2026

ONOMO Hotel Waterfront

24 Alfred Street, V& A Waterfront Cape Town Western Cape

Fully refundableReserve now, pay when you stay

$63 nightly

$74 total

Sep 28 - Sep 29

Total with taxes and fees

9/10 Wonderful! (419 reviews)

"The staff were very friendly, helpful and professional. Rooms were very clean. Would stay here again."

Reviewed on Sep 15, 2026

Hotel Verde Cape Town Airport

15 Michigan Street, Airport Industria Cape Town Western Cape

$157 nightly

$181 total

Sep 24 - Sep 25

Total with taxes and fees

9.6/10 Exceptional! (1,004 reviews)

"A comfortable hotel for an overnight stay. Was pleasantly surprised at how “high end” it felt. Had dinner there. Quite an extensive menu, though the quality was nothing special, though service was was good."

Reviewed on Sep 21, 2026

See all 6,522 properties in Windermere

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.