Windsor Hills Vacation Packages

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Top Holiday Package Deals in Windsor Hills

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at The Welk, San Diego Area

Hyatt Vacation Club at The Welk, San Diego Area

3.5 out of 5
Lawrence Welk Resort Village
Price was CA $749, price is now CA $455 per person
CA $455
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
8.2/10 Very Good! (1,429 reviews)
Loved the pool options

Reviewed on Sep 8, 2025

Alila Marea Beach Resort Encinitas, a Hyatt Luxury Resort

Alila Marea Beach Resort Encinitas, a Hyatt Luxury Resort

5 out of 5
Price was CA $3,328, price is now CA $1,473 per person
CA $1,473
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to San Diego (SAN)
8.8/10 Excellent! (207 reviews)
Everything was excellent as advertised.

Reviewed on Aug 11, 2025

Sand Castle Inn

Sand Castle Inn

2.5 out of 5
Price was CA $1,369, price is now CA $785 per person
CA $785
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
8.2/10 Very Good! (480 reviews)
Conveniently located. Spacious room. Best quality and pricing combination in Imperial Beach.

Reviewed on Sep 9, 2025

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was CA $2,268, price is now CA $1,352 per person
CA $1,352
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
8.4/10 Very Good! (1,571 reviews)
Prefer not to answer

Reviewed on Sep 10, 2025

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Price was CA $2,290, price is now CA $1,421 per person
CA $1,421
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Diego (SAN)
9/10 Wonderful! (1,016 reviews)
Overall, had a good stay. The location of the property made is extremely convenient getting around Gaslamp. Property was clean and the staff were great. There were a couple of issues that prevented me giving them 5 stars that I’ll elaborate on. 1) When I called the main the desk to get some additional towels delivered, I was put on hold for quite some time, probably a good 30 minutes. Not sure if they were short staffed or just forgotten about but those things leave a sour taste when it comes to hospitality. Eventually, we just tracked down a maid and grabbed towels from them. 2) We were given a ADA room, which was probably the only room they had available at the time we checked in (1:45PM). It wasn’t a bad thing but the bench inside the tub made it very inconvenient to shower since it took up nearly 1/2 the tub. Other than those things, I would probably stay here again and get a regular room.

Reviewed on Sep 8, 2025

Windsor Hills Hotel Deals

Manchester Grand Hyatt San Diego

Manchester Grand Hyatt San Diego

4 out of 5
1 Market Pl, San Diego, CA
The price is CA $359 per night from Oct 11 to Oct 12
CA $359
CA $491 total
Oct 11 - Oct 12
includes taxes & fees
9/10 Wonderful! (2,810 reviews)
"Location is amazing"

Reviewed on Sep. 9, 2025

Manchester Grand Hyatt San Diego
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 CA $211 per night from Sep 29 to Sep 30
CA $211
CA $279 total
Sep 29 - Sep 30
includes taxes & fees
8.2/10 Very Good! (5,888 reviews)
Wyndham Bayside
"Great experience. Location would be impossible to beat. No problems or issues with our enjoyable stay."

Reviewed on Sep. 10, 2025

Wyndham San Diego Bayside
Palihotel San Diego Gaslamp Quarter

Palihotel San Diego Gaslamp Quarter

4 out of 5
830 Sixth Avenue, San Diego, CA
The price is CA $143 per night from Sep 29 to Sep 30
CA $143
CA $166 total
Sep 29 - Sep 30
includes taxes & fees
8.6/10 Excellent! (1,751 reviews)
"I like the 1950’s vibe and staff was great."

Reviewed on Sep. 10, 2025

Palihotel San Diego Gaslamp Quarter
See all 8,016 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Windsor Hills vacation package cost?
From as little as CA $455. Yes, you read that correctly. Our Windsor Hills vacation 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 vacation 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 vacation?
It can be tricky to know exactly when is the perfect time to book your Windsor Hills vacation. 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 vacation 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 vacation plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Windsor Hills Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation 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 vacation package?
Plans can change in a flash, so yes, you can. You may be able to cancel or change your Windsor Hills vacation 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

CA $109
per adult
82% of travellers recommend
LEGOLAND® California Resort
San Diego City Lights Night Tour

San Diego City Lights Night Tour

CA $60
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

CA $170
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.