Windermere Vacations from $2,212

Book a Hotel + Flight or Car together to unlock savings

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.
Asara Wine Estate & Hotel

Asara Wine Estate & Hotel

5 out of 5
Price was $2,598, price is now $2,212 per person
$2,212
per person
Feb 16 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Cape Town (CPT)
9.4/10 Exceptional! (276 reviews)
Beautiful property very peaceful

Reviewed on Dec 23, 2025

Cape Cadogan Boutique Hotel

Cape Cadogan Boutique Hotel

5 out of 5
Cape Town City Centre
Price was $4,279, price is now $3,250 per person
$3,250
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cape Town (CPT)
9.6/10 Exceptional! (51 reviews)
Accommodating staff, excellent location, and luxurious rooms.

Reviewed on Jan 10, 2026

One&Only Cape Town

One&Only Cape Town

5 out of 5
Victoria and Alfred Waterfront
Price was $4,434, price is now $3,547 per person
$3,547
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cape Town (CPT)
9.6/10 Exceptional! (366 reviews)
The most amazing hotel. Beyond amazing

Reviewed on Nov 26, 2025

O' Two Hotel

O' Two Hotel

4 out of 5
Sea Point Promenade
Price was $3,014, price is now $2,421 per person
$2,421
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cape Town (CPT)
9.6/10 Exceptional! (55 reviews)
Cute boutique. Lobby smelled great. Jug of ice cold water flavored with lemon or cucumbers or strawberries, nice touch. Great decor. Staff friendly and receptive and helpful. The room although small had great windows, view of golf course. Terrace view of ocean. Shower very hot which was outstanding. . Thin walls could hear shower next door. Terrace close together could smell smoke from room next door. Would prefer no smoking Period.

Reviewed on Jul 13, 2025

Spectacular Holiday Villa w Private Pool Gym Prima Views

Spectacular Holiday Villa w Private Pool Gym Prima Views

2 out of 5
Camps Bay
Price was $5,412, price is now $4,612 per person
$4,612
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Cape Town (CPT)
No reviews

Where to stay in Windermere

Find the best Windermere areas and neighborhoods for the activities you enjoy most. Learn more about Windermere
Victoria and Alfred Waterfront featuring a marina

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.

Find hotels in Victoria and Alfred Waterfront

Windermere Hotel Deals

Road Lodge Cape Town International Airport

Road Lodge Cape Town International Airport

3 out of 5
Adjoining BP Service & Filling Station Cape Town Western Cape
$59 nightly
The price is $69 total per night from Jan 17 to Jan 18
$69 total
Jan 17 - Jan 18
Total with taxes and fees
8.2/10 Very Good! (1,058 reviews)
Polite staff and clean room.

Reviewed on Jan 6, 2026

Road Lodge Cape Town International Airport
ONOMO Hotel Waterfront

ONOMO Hotel Waterfront

3.5 out of 5
24 Alfred Street, V& A Waterfront Cape Town Western Cape
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Jan 20 to Jan 21
$72 total
Jan 20 - Jan 21
Total with taxes and fees
8.8/10 Excellent! (315 reviews)
We found everything well organised staff were super friendly the use of being able to leave luggage was also a benefit. There is nothing that I could think of that was not catered also accessibility of the waterfront

Reviewed on Jan 7, 2026

ONOMO Hotel Waterfront
AC Hotel by Marriott Cape Town Waterfront

AC Hotel by Marriott Cape Town Waterfront

4 out of 5
Dockrail Road, Foreshore Cape Town Western Cape
$192 nightly
The price is $221 total per night from Jan 31 to Feb 1
$221 total
Jan 31 - Feb 1
Total with taxes and fees
9.2/10 Wonderful! (661 reviews)
Brilliant hotel overall. The location was a little tricky to find at first, but once there it was nice. The rooms were modern, very clean, and spacious, making the stay comfortable and relaxing. I must say the breakfast was excellent — a great variety of options and very high quality, definitely ...

Reviewed on Jan 9, 2026

AC Hotel by Marriott Cape Town Waterfront
See all 6,618 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Windermere

Camps Bay Beach showing a sandy beach and a coastal town

Camps Bay Beach

See and be seen, admire beautiful sunsets and go hiking in the famous Twelve Apostles at one of Cape Town’s most stylish beaches.

Camps Bay Beach
Clifton Bay Beach showing a coastal town, rocky coastline and a sandy beach

Clifton Bay Beach

Soft white sand, aquamarine water, striking mountain views and picture-perfect sunsets lure visitors to this collection of four fashionable beaches.

Clifton Bay Beach
Table Mountain which includes landscape views and mountains

Table Mountain

One of the world’s oldest mountains creates an iconic backdrop to the Cape Town skyline. Climb to the summit for breathtaking views of the surrounding coast.

Table Mountain

Things to do

Quad biking at Atlantis White Sand Dunes Cape Town

WILDX Atlantis QUAD BIKE ADVENTURE + PHOTO OPS CAPE TOWN

$48
per adult
WILDX Atlantis QUAD BIKE ADVENTURE + PHOTO OPS CAPE TOWN
Cape Town: Half-Day City Tour

Guided Half-Day City Tour with Table Mountain

$58
per adult
Guided Half-Day City Tour with Table Mountain
Cape Town: Bo-Kapp Walking Tour and Malay Cooking Class

Cape Town: Bo-Kapp Walking Tour and Malay Cooking Class

$66
per adult
Cape Town: Bo-Kapp Walking Tour and Malay Cooking Class
See all activities in Cape Town
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.