Windsor Hills Vacations from $385

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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.
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
Save 100% on your flight
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.2/10 Very Good! (1,310 reviews)
The room was absolutely beautiful! Great beds with perfect linens. The pools were amazing! Thank you!

Reviewed on Jul 14, 2025

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
per person
Aug 22 - Aug 28
found 2 days ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.4/10 Very Good! (1,488 reviews)
Our room was way too small and I was less than pleased with the amenities charge, especially since there wasn’t even a pool. Staff was exceptionally nice.

Reviewed on Jul 14, 2025

Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Save 100% on your flight
per person
Aug 22 - Aug 28
found 2 days ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.6/10 Excellent! (2,170 reviews)
Amazing place to relax and unwind.

Reviewed on Jul 15, 2025

Kona Kai San Diego

Kona Kai San Diego

4 out of 5
Point Loma
Save 100% on your flight
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
8.4/10 Very Good! (1,004 reviews)
The room was beautiful and clean.

Reviewed on Jul 15, 2025

Barsala City Villas

Barsala City Villas

2.5 out of 5
Downtown San Diego
Save 100% on your flight
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
No reviews

Windsor Hills Hotel Deals

Handlery Hotel
Handlery Hotel
3.5 out of 5
950 Hotel Cir N, San Diego, CA
$111 nightly
The price is $128 total per night from Jul 21 to Jul 22
$128 total
Jul 21 - Jul 22
Total includes taxes and fees
8/10 Very Good! (1,864 reviews)
"Nice experience"

Reviewed on Jul 12, 2025

Handlery Hotel
Wyndham San Diego Bayside
Wyndham San Diego Bayside
4 out of 5
1355 N Harbor Drive, San Diego, CA
$177 nightly
The price is $205 total per night from Jul 21 to Jul 22
$205 total
Jul 21 - Jul 22
Total includes taxes and fees
8.2/10 Very Good! (5,720 reviews)
"Great staff! The only thing was that our deadbolt didn’t work. Otherwise, it was great!"

Reviewed on Jul 13, 2025

Wyndham San Diego Bayside
Marriott Marquis San Diego Marina
Marriott Marquis San Diego Marina
4 out of 5
333 W Harbor Dr, San Diego, CA
$272 nightly
The price is $316 total per night from Aug 13 to Aug 14
$316 total
Aug 13 - Aug 14
Total includes taxes and fees
9/10 Wonderful! (1,751 reviews)
"Overall a good experience. Room doors bang loudly."

Reviewed on Jul 14, 2025

Marriott Marquis San Diego Marina
See all 7,829 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Discover the most popular places to visit in Windsor Hills

Mount Helix Park

5/5(1 review)

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

LEGOLAND® California Resort

LEGOLAND® California Resort

$79
per adult
82% of travellers recommend
LEGOLAND® California Resort
San Diego City Lights Night Tour

San Diego City Lights Night Tour

$46
per adult
96% 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

$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.