Windsor Hills Vacations from $580

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Your Windsor Hills Vacation

Our Windsor Hills vacation packages are a speedy and practical way to organize and book your next adventure. Discover the heart and soul of this unique neighborhood without the pressure of having to plan everything yourself. When you want to take in the sights, your trip to Windsor Hills has to include a visit to Mount Helix Park and Computer Museum of America. Expedia can put your plans into action. Book your dream Windsor Hills vacation today.

The Latest Windsor Hills Vacation Packages

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

Sand Castle Inn

2.5 out of 5
Save 100% on your flight
Price was $1,051, price is now $580 per person
$580
per person
Jan 24 - Jan 31
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.2/10 Very Good! (486 reviews)
View and service were great.

Reviewed on Nov 9, 2025

Pacific View Inn

Pacific View Inn

2 out of 5
Pacific Beach
Save 100% on your flight
Price was $1,080, price is now $636 per person
$636
per person
Jan 24 - Jan 31
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
7.8/10 Good! (1,011 reviews)
Room was super clean and very comfortable. Location is amazing and the staff were SUPER friendly! Will definitely stay here again.

Reviewed on Nov 6, 2025

Kona Kai San Diego

Kona Kai San Diego

4 out of 5
Point Loma
Price was $1,106, price is now $690 per person
$690
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to San Diego (SAN)
8.4/10 Very Good! (1,010 reviews)
Great spot. Was a dream.

Reviewed on Nov 10, 2025

Granger Hotel Gaslamp Quarter, A Member Of Design Hotels

Granger Hotel Gaslamp Quarter, A Member Of Design Hotels

4 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,364, price is now $856 per person
$856
per person
Jan 24 - Jan 31
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
9.2/10 Wonderful! (560 reviews)
Very cool boutique type hotel. Easy check in and the room was very clean, small but clean. The elevator is slow so take the stairs if you can!

Reviewed on Nov 9, 2025

Big 7 Motel Chula Vista I-5

Big 7 Motel Chula Vista I-5

2.5 out of 5
Price was $1,440, price is now $914 per person
$914
per person
Jan 11 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to San Diego (SAN)
6.2/10 (940 reviews)
Property is old and seems run down

Reviewed on Jul 26, 2025

Windsor Hills Hotel Deals

Hilton San Diego Mission Valley

Hilton San Diego Mission Valley

4 out of 5
901 Camino Del Rio S, San Diego, CA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Nov 17 to Nov 18
$131 total
Nov 17 - Nov 18
Total with taxes and fees
8/10 Very Good! (2,155 reviews)
Given the wrong room but they made up for it with free breakfast and free parking! Security fee is ridiculously expensive for no reason though.

Reviewed on Nov 10, 2025

Hilton San Diego Mission Valley
Hampton Inn & Suites by Hilton San Diego SeaWorld

Hampton Inn & Suites by Hilton San Diego SeaWorld

3 out of 5
3888 Greenwood St, San Diego, CA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Nov 17 to Nov 18
$137 total
Nov 17 - Nov 18
Total with taxes and fees
9/10 Wonderful! (278 reviews)
The staff was friendly and went above and beyond. The rooms were clean and newly upgraded. Plenty of parking even on a Saturday.

Reviewed on Nov 10, 2025

Hampton Inn & Suites by Hilton San Diego SeaWorld
Hard Rock Hotel San Diego

Hard Rock Hotel San Diego

4 out of 5
207 5th Ave, San Diego, CA
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $227 total per night from Nov 22 to Nov 23
$227 total
Nov 22 - Nov 23
Total with taxes and fees
8.8/10 Excellent! (3,041 reviews)
Rooms need an update

Reviewed on Nov 6, 2025

Hard Rock Hotel San Diego
See all 8,045 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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Discover the most popular places to visit in Windsor Hills

Mount Helix Park

Learn about the local history of Casa de Oro-Mount Helix when you spend time at Mount Helix Park. Amble around this family-friendly area's waterfront or attend a sporting event.

Mount Helix Park

Computer Museum of America

You can spend an afternoon studying the exhibits at Computer Museum of America during your trip to La Mesa. Attend a sporting event while in this walkable area or simply enjoy the top-notch restaurants.

Computer Museum of America

Things to do

San Diego: Museum of Illusions Entry Ticket

San Diego: Museum of Illusions Entry Ticket

$35
per adult
74% of travellers recommend
San Diego: Museum of Illusions Entry Ticket
San Diego Old Town Trolley Hop-On Hop-Off Tour

San Diego Old Town Trolley Hop-On Hop-Off Tour

$95
per adult
94% of travellers recommend
San Diego Old Town Trolley Hop-On Hop-Off Tour
Go City: San Diego Explorer Pass - Choose 2 to 7 Attractions

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

$124
per adult
86% 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.