Middletown Vacations from $550

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Your Middletown Vacation

Middletown is calling your name! Whatever type of adventure you're organizing, you can immerse yourself in the best of this neighborhood with a Middletown vacation package. Some popular nearby attractions to check out during your trip to Middletown include San Diego Zoo, Balboa Park and University of San Diego. Expedia is here to help put your travel plans into action. Book your ultimate Middletown vacation today.

The Latest Middletown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

Downtown San Diego
Save 100% on your flight
$550
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9/10 Wonderful! (1,516 reviews)
The Sofia Hotel

The Sofia Hotel

Downtown San Diego
$803
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.6/10 Excellent! (2,550 reviews)
Nice hotel, well located near the Gaslamp.

Reviewed on Sep 3, 2026

Ocean Villas of Carlsbad

Ocean Villas of Carlsbad

Carlsbad Village
$1,197
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9/10 Wonderful! (23 reviews)
Paradise Point Resort & Spa

Paradise Point Resort & Spa

Mission Bay
Save 100% on your flight
$1,272
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.8/10 Excellent! (2,853 reviews)
Shore House at The Del, LXR Hotels & Resorts

Shore House at The Del, LXR Hotels & Resorts

Historic Downtown Coronado
Save 100% on your flight
$1,746
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
9.2/10 Wonderful! (175 reviews)

Where to stay in Middletown

Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown
A grand building with a central fountain, palm trees, and a flag.

Downtown San Diego

3 out of top 10 points of interest in this area

Cultural and financial hub, Downtown San Diego boasts the Symphony, Opera, theaters, museums, and historic sites like Gaslamp Quarter. Enjoy diverse shops, dining, nightlife, and convenient public transport options.

A pier extending into calm waters with people on it and a sandy beach with seaweed and a few individuals.

Pacific Beach

Boasting a lively nightlife scene, Pacific Beach offers miles of sandy shores, a bustling 3.2-mile boardwalk, and attractions like Crystal Pier and Kate Sessions Park. Enjoy local shops, bars, and eateries along the vibrant walkway.

A sandy beach with a lifeguard tower, ocean waves, and people in the distance.

Mission Beach

Spanning nearly two miles of oceanfront, this sandbar community offers sunbathing, surfing, and beach volleyball, with nearby attractions like Belmont Park's Giant Dipper Roller Coaster and SeaWorld in Mission Bay Park.

A lively street scene with outdoor seating at various bars and restaurants, including 'The Field' and 'Sloppy Joe's'.

Gaslamp Quarter

Downtown San Diego's historic district boasts Victorian-era buildings, now housing vibrant restaurants, shops, and entertainment venues. Stroll from Broadway to Harbor Drive, and 4th to 6th Avenue, admiring the newly installed gaslamps at Market Street.

An aerial view of a coastal city with a marina, a large body of water, and a peninsula with buildings.

Mission Bay

1 out of top 10 points of interest in this area

If you're spending some time in Mission Bay, Mission Bay and Mission and Pacific Beaches are top sights worth seeing.

Middletown Hotel Deals

Manchester Grand Hyatt San Diego

Manchester Grand Hyatt San Diego

1 Market Pl San Diego CA
Fully refundableReserve now, pay when you stay
$246 nightly
$285 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (2,830 reviews)
"Room was excellent, very comfortable and stylish. Ordering for room delivery a little complicated; QR code on menu linked to multiple webpages that were not intuitive nor included breakfast ordering options- tried ordering at dinner too and webpage would not allow order to be placed- ended up calling ..."

Reviewed on Sep 3, 2026

Manchester Grand Hyatt San Diego
California Suites Hotel

California Suites Hotel

5415 Clairemont Mesa Blvd San Diego CA
Fully refundableReserve now, pay when you stay
$89 nightly
$102 total
Sep 20 - Sep 21
Total with taxes and fees
California Suites Hotel
Wyndham San Diego Bayside

Wyndham San Diego Bayside

1355 N Harbor Drive San Diego CA
Fully refundableReserve now, pay when you stay
$182 nightly
$211 total
Sep 7 - Sep 8
Total with taxes and fees
Wyndham San Diego Bayside
See all 8,750 properties in Middletown
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.

Stay near popular Middletown attractions

The Casbah San Diego

The Casbah San Diego is just one of the places to see in San Diego, so why not enjoy the other things to explore during your travels? Stroll along the waterfront or experience the area's live music.
See properties

Things to do

San Diego Padres Baseball Game at Petco Park

San Diego Padres Baseball Game at Petco Park

$44
per adult
San Diego Padres Baseball Game at Petco Park
San Diego: 3 Hour Whale Watching Cruise

San Diego: 3 Hour Whale Watch Cruise with Legacy Whale Watch

$34
per adult
88% of travellers recommend
San Diego: 3 Hour Whale Watch Cruise with Legacy Whale Watch
See all activities in San Diego
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.