Middletown Vacations from $478

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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.
Quiet Mind Mountain Lodge, Retreat and Spa

Quiet Mind Mountain Lodge, Retreat and Spa

4.5 out of 5
Save 100% on your flight
Price was $810, price is now $478 per person
$478
per person
Mar 19 - Mar 25
just found
Roundtrip flight included
Seattle (SEA) to San Diego (SAN)
9.2/10 Wonderful! (558 reviews)
The property is beautiful!!!

Reviewed on Dec 27, 2025

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Save 100% on your flight
Price was $1,205, price is now $597 per person
$597
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.4/10 Very Good! (1,627 reviews)
Small room but very clean and comfortable

Reviewed on Jan 12, 2026

Los Bungalows

Los Bungalows

2.5 out of 5
Save 100% on your flight
Price was $1,292, price is now $773 per person
$773
per person
Mar 20 - Mar 27
found 19 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.2/10 Very Good! (498 reviews)
The room was spotless and everything had been recently renovated to create a real beach bungalow vibe. Literally across the street from the pier and beach. This was a tremendous value and I will be staying there again.

Reviewed on Jan 6, 2026

Paradise Point Resort & Spa

Paradise Point Resort & Spa

4 out of 5
Mission Bay
Save 100% on your flight
Price was $955, price is now $574 per person
$574
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
8.6/10 Excellent! (2,326 reviews)
Clean Quite convenient

Reviewed on Jan 9, 2026

La Jolla Cove Suites

La Jolla Cove Suites

3 out of 5
Village of La Jolla
Save 100% on your flight
Price was $1,250, price is now $767 per person
$767
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San Diego (SAN)
7/10 Good! (1,075 reviews)
Beautiful view. Friendly and helpful staff.

Reviewed on Jan 10, 2026

Where to stay in Middletown

Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown
US Grant Hotel

Downtown San Diego

4 out of top 10 points of interest in this area
4.5/5(8,497 area reviews)

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.

Find hotels in Downtown San Diego

Middletown Hotel Deals

Sheraton San Diego Resort

Sheraton San Diego Resort

4 out of 5
1380 Harbor Island Dr San Diego CA
Fully refundableReserve now, pay when you stay
$226 nightly
The price is $260 total per night from Feb 6 to Feb 7
$260 total
Feb 6 - Feb 7
Total with taxes and fees
8.2/10 Very Good! (3,226 reviews)
The room was beautiful

Reviewed on Jan 8, 2026

Sheraton San Diego Resort
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
$136 nightly
The price is $156 total per night from Jan 25 to Jan 26
$156 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (3,280 reviews)
Beautiful location, great staff, always a pleasure to stay here

Reviewed on Jan 11, 2026

Bay Club Hotel & Marina
Courtyard by Marriott San Diego Downtown Little Italy

Courtyard by Marriott San Diego Downtown Little Italy

4 out of 5
1646 Front St San Diego CA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $147 total per night from Jan 19 to Jan 20
$147 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (229 reviews)
The staff was amazing. The room was clean and very comfortable. The only complaint was not all elevators were in operation. This caused a tremendous wait time.

Reviewed on Jan 12, 2026

Courtyard by Marriott San Diego Downtown Little Italy
See all 8,576 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Middletown

San Diego Zoo featuring landscape views, zoo animals and a pond

San Diego Zoo

See nature up-close and personal at one of the country’s largest and most educational zoos.

San Diego Zoo
San Diego Convention Center

San Diego Convention Center

Whether you come for Comic-Con or a medical convention, this huge gathering place in the Marina District of San Diego will more than satisfy your needs.

San Diego Convention Center
Mission Bay featuring a sandy beach

Mission Bay

Mingle with eccentric locals at bohemian beaches, soak up the sun on a Jet Ski and fish from marshy islands at San Diego’s premier water park.

Mission Bay

Things to do

San Diego Whale Watching Tour

San Diego Whale Watching & Dolphin Cruise

$71
per adult
86% of travellers recommend
San Diego Whale Watching & Dolphin Cruise
San Diego Old Town Trolley Hop-On Hop-Off Tour

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

$55
per adult
94% of travellers recommend
San Diego Old Town Trolley Hop-On Hop-Off Tour
San Diego: Luggage Storage in Marina

San Diego: Luggage Storage in Marina

$9
per adult
80% of travellers recommend
San Diego: Luggage Storage in Marina
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.