Windsor Hills Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Windsor Hills

Handlery Hotel

Handlery Hotel

3.5 out of 5
950 Hotel Cir N, San Diego, CA
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,996 reviews)
Handlery Stay August 21-23
"Nice rooms, bed is a little firm, pillows were OUTSTANDING. Could use better TV's. Lobby bar was closed both night. Both restaurants were good. The staff was very friendly. As for location with being able to walk to stores or quick marts, terrible, nothing close."

Reviewed on 24 Aug, 2025

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Handlery Hotel
Wyndham San Diego Bayside

Wyndham San Diego Bayside

4 out of 5
1355 N Harbor Drive, San Diego, CA
Fully refundableReserve now, pay when you stay
The price is S$259 per night from 1 Sept to 2 Sept
S$259
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (5,858 reviews)
"Huge, lovely room with great views regardless of what side or tower! Friendly staff, clean and secure property"

Reviewed on 27 Aug, 2025

Wyndham San Diego Bayside
Bay Club Hotel & Marina

Bay Club Hotel & Marina

3.5 out of 5
2131 Shelter Island Dr, San Diego, CA
Fully refundableReserve now, pay when you stay
The price is S$185 per night from 8 Sept to 9 Sept
S$185
8 Sept - 9 Sept
includes taxes & fees
Bay Club Hotel & Marina
See all 7,895 properties in Windsor Hills
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.

Frequently asked questions

How much does a Windsor Hills holiday package cost?
From as little as . Yes, you read that correctly. Our Windsor Hills holiday packages are a simple way to make your budget stretch further. Combine your hotels, flights and car rentals and explore this fabulous destination.
How do I get a cheap travel package to Windsor Hills?
Booking a Windsor Hills holiday package with Expedia is one of the easiest ways to save. We offer access to over 550 partner airlines and 1,000,000 hotels around the world. With such a fantastic range to pick from, you'll have no trouble putting together your dream escape.
Where should I stay in Windsor Hills?
There's loads to explore in Windsor Hills, so spend your nights close to its top attractions and spend more time sightseeing. Mount Helix Park is one place to put on your to-do list.
What are the top hotels in Windsor Hills?
Romantic View Home Centrally Located In Windsor Hills is one of Windsor Hills's leading properties. Check in to a room here and you'll be able to slumber peacefully knowing you're in good hands.
How far in advance should I book my Windsor Hills holiday?
It can be tricky to know exactly when is the perfect time to book your Windsor Hills holiday. But generally the earlier you book, the more affordable the prices. In some cases, you can secure your flights and hotels nearly 12 months prior to your departure date. If you're hoping for a last-minute getaway, no need to fret! There are great deals advertised on Expedia every day.
What does an Expedia Windsor Hills travel package include?
It all comes down to what sort of trip you have in mind. Windsor Hills holiday deals can include car rentals, flights and hotels. You can mix and match to find the package that suits you. You can also add on activities and experiences after you've booked to score even bigger discounts.
What should I know before booking a Windsor Hills travel package?
A travel package can be easier on the wallet than separately booking all you need for your escape. For example, combine your hotels, flights and rental cars and score impressive savings. Whatever your holiday plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Windsor Hills Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines all over the world, so you have lots of choice when arranging your Windsor Hills trip.
If I'm not able to travel, can I cancel my Windsor Hills holiday package?
Plans can change in a flash, so yes, you can. You may be able to cancel or change your Windsor Hills holiday package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, airline or hotel may charge a fee. Want more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Things to do

LEGOLAND® California Resort

LEGOLAND® California Resort

S$101
per adult
82% of travellers recommend
LEGOLAND® California Resort
San Diego City Lights Night Tour

San Diego City Lights Night Tour

S$59
per adult
94% of travellers recommend
San Diego City Lights Night Tour
San Diego Explorer Pass: Save up to 50 Percent - Includes USS Midway

San Diego Explorer Pass: Save up to 50 Percent - Includes USS Midway

S$159
per adult
88% of travellers recommend
San Diego Explorer Pass: Save up to 50 Percent - Includes USS Midway
See all activities in La Mesa

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.