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.
Hilton San Diego Gaslamp Quarter

Hilton San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Price was CA $1,606, price is now CA $785 per person
CA $785
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Diego (SAN)
8.8/10 Excellent! (190 reviews)
The hotel was great- clean- in walking distance to Petco Park, the Midway, and all of the Gaslamp restaurants and shops. The valet staff was quick and polite- and the process was so easy when we needed our car. The hotel staff were helpful and kind- and I got texts daily to check in on our stay. They even helped with restaurant recommendations! If I ever get to visit San Diego again- I will def stay here!

Reviewed on Aug. 18, 2025

Empress Hotel of La Jolla

Empress Hotel of La Jolla

3 out of 5
Village of La Jolla
Price was CA $2,012, price is now CA $1,289 per person
CA $1,289
per person
Oct 2 - Oct 9
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to San Diego (SAN)
9/10 Wonderful! (999 reviews)
We have always had a positive experience for several years at Empress Hotel, for some reason, they got rid of the valet. Not user friendly! Also, yes, we left around 12:00 noon on Saturday, however, no room cleaning service by the time we returned around 6:00 PM.

Reviewed on Aug. 24, 2025

Estancia La Jolla Hotel & Spa

Estancia La Jolla Hotel & Spa

4 out of 5
La Jolla Farms
Price was CA $2,444, price is now CA $1,566 per person
CA $1,566
per person
Nov 20 - Nov 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Diego (SAN)
9/10 Wonderful! (261 reviews)
I loved how quiet and peaceful this hotel was! The entire staff was so friendly and helpful. It was such a relaxing stay, I would highly reccomend.

Reviewed on Aug. 26, 2025

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was CA $2,804, price is now CA $1,803 per person
CA $1,803
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Diego (SAN)
8.4/10 Very Good! (1,543 reviews)
I stayed at The Sofia Hotel in downtown San Diego and loved its mix of historic charm and modern comfort. The location is excellent—just steps from the Gaslamp Quarter, the waterfront, and conveniently close to the Santa Fe train station, making travel super easy.

Reviewed on Aug. 28, 2025

The DEXTRO Little Italy, BW Premier Collection

The DEXTRO Little Italy, BW Premier Collection

3 out of 5
Downtown San Diego
Price was CA $2,591, price is now CA $1,716 per person
CA $1,716
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Montreal (YUL) to San Diego (SAN)
8.6/10 Excellent! (348 reviews)
It was a great property. Not the best of views, but a comfortable place to rest at night

Reviewed on Aug. 29, 2025

Windsor Hills Hotel Deals

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 $209 per night from Sep 1 to Sep 2
CA $209
CA $277 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (5,889 reviews)
Great view. Great location. Great shuttle.
"I had a really great time. The room could have been cleaner on arrival."

Reviewed on Aug. 24, 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 CA $205 per night from Sep 3 to Sep 4
CA $205
CA $236 total
Sep 3 - Sep 4
includes taxes & fees
9/10 Wonderful! (2,850 reviews)
"Conveniently located by the bay with easy access to downtown San Diego and the airport. We were delightfully impressed with the bar/dining room service staff during happy hour/dinner."

Reviewed on Aug. 27, 2025

Bay Club Hotel & Marina
The DEXTRO Little Italy, BW Premier Collection

The DEXTRO Little Italy, BW Premier Collection

3 out of 5
1617 1st Avenue, San Diego, CA
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Sep 1 to Sep 2
CA $162
CA $188 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,133 reviews)
"We had a great stay here. The bed and pillows were super comfortable. The parking was cheap and easily accessible. The staff was really friendly."

Reviewed on Aug. 24, 2025

The DEXTRO Little Italy, BW Premier Collection
See all 7,926 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.
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Frequently asked questions

How much does a Windsor Hills vacation package cost?
From as little as CA $785. 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
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San Diego City Lights Night Tour

San Diego City Lights Night Tour

CA $63
per adult
94% of travellers recommend
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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 $171
per adult
88% of travellers recommend
San Diego Explorer Pass: Save up to 50 Percent - Includes USS Midway
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.