Middletown Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- The Sofia Hotel
Jul 3 - Jul 6The Sofia Hotel + Flight
Downtown San Diego3 nights8.6/10 - Excellent (2,144 reviews)"Great staff, wonderful ambiance. Close to dining options. Great value fir your money."Reviewed May 31, 2026Roundtrip • Chicago (ORD) - Carlsbad (CLD)ORD - CLD • 1 stop CLD - ORD • 1 stop - Los Bungalows
Jul 15 - Jul 21Los Bungalows + Flight
Imperial Beach6 nights8.2/10 - Very Good (534 reviews)"Loved the stay here great location the kids really liked it walking distance from beach pizza restaurants felt very safe talking to the neighbors they said it was a great area try the pizza"Reviewed May 24, 2026Roundtrip • Chicago (ORD) - San Diego (SAN)ORD - SAN • 1 stop SAN - ORD • 1 stop - Hyatt Vacation Club at The Welk, San Diego Area
Aug 3 - Aug 9Hyatt Vacation Club at The Welk, San Diego Area + Flight
Lawrence Welk Resort Village6 nights8.4/10 - Very Good (1,845 reviews)"Place is excellent. Staff is friendly and excellent customer service. Room was clean and modern. Family friendly environmen"Reviewed May 31, 2026Roundtrip • Chicago (MDW) - San Diego (SAN)MDW - SAN • Nonstop SAN - ORD • Nonstop - The Artifact Inn
Jul 6 - Jul 11The Artifact Inn + Flight
Downtown San Diego5 nights9.2/10 - Wonderful (78 reviews)"A lovely and welcoming oasis. Exactly as advertised. Staff were very helpful. Would definitely stay here again."Reviewed May 24, 2026Roundtrip • Chicago (ORD) - San Diego (SAN)ORD - SAN • Nonstop SAN - ORD • Nonstop - Guesthouse Hotel at La Valle
Jul 6 - Jul 11Guesthouse Hotel at La Valle + Flight
Rancho Santa Fe5 nights9.4/10 - Exceptional (122 reviews)"Great place to stay in the San Diego area, located in a high-end neighborhood inside a golf club. The rooms, which appear to have been recently and tastefully renovated, are spacious, clean, and quiet. The welcome amenities (gummy bears and nuts) are a nice touch. We will definitely stay here again when we’re back in the area. The only minor downside for us was the lack of a full sit-down breakfast service, although there are plenty of places for breakfast just a short drive away."Reviewed May 18, 2026Roundtrip • Chicago (ORD) - San Diego (SAN)ORD - SAN • Nonstop SAN - MDW • Nonstop
Where to stay in Middletown
Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown
Downtown San Diego
4 out of top 10 points of interest in this area
4.5/5(8,598 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.
Middletown Hotel Deals
The Sofia Hotel
150 W Broadway San Diego CA
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $223 total per night from Jun 29 to Jun 30
$223 total
Jun 29 - Jun 30
Total with taxes and fees
8.6/10 Excellent! (2,144 reviews)
"Great staff, wonderful ambiance. Close to dining options. Great value fir your money."
Reviewed on May 31, 2026
Manchester Grand Hyatt San Diego
1 Market Pl San Diego CA
Fully refundableReserve now, pay when you stay
$276 nightly
The price is $320 total per night from Jun 5 to Jun 6
$320 total
Jun 5 - Jun 6
Total with taxes and fees
9/10 Wonderful! (2,827 reviews)
"It’s beautiful, clean, close to everything, food is good too’."
Reviewed on May 30, 2026
Hard Rock Hotel San Diego
207 5th Ave San Diego CA
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $246 total per night from Jun 7 to Jun 8
$246 total
Jun 7 - Jun 8
Total with taxes and fees
9/10 Wonderful! (3,762 reviews)
"The valet parking being $70 dollars and our vehicle being returned with what looks like someone punched out drivers side panel."
Reviewed on May 30, 2026
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.
Discover the most popular places to visit in Middletown
San Diego Zoo
4.5/5(3,637 reviews)
See nature up-close and personal at one of the country’s largest and most educational zoos.
San Diego Convention Center
4.5/5(1,324 reviews)
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.
USS Midway Museum
4.5/5(2,442 reviews)
Experience the thrills and hardships of Navy life at this waterfront museum which has become a San Diego landmark.
Things to do
Oceanside Whale and Dolphin Watching Adventures
$57
per adult
90% of travellers recommend
San Diego Old Town Trolley Hop-On Hop-Off Tour
$57
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.