Middletown Vacations from $250

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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.
The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was $575, price is now $250 per person
$250
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
16.8/10 Exceptional! (1,627 reviews)
Gave me the free upgrade. Loving staff. Thank you!!

Reviewed on Nov 17, 2025

Los Bungalows

Los Bungalows

2.5 out of 5
Price was $1,191, price is now $396 per person
$396
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
16.4/10 Exceptional! (497 reviews)
View and service were great.

Reviewed on Nov 9, 2025

Fairmont Grand Del Mar

Fairmont Grand Del Mar

5 out of 5
Carmel Valley
Price was $1,595, price is now $765 per person
$765
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
19.2/10 Exceptional! (907 reviews)
Comfortable accommodations and beautiful accommodations

Reviewed on Oct 25, 2025

Margaritaville Hotel San Diego Gaslamp Quarter

Margaritaville Hotel San Diego Gaslamp Quarter

4 out of 5
Downtown San Diego
Price was $735, price is now $355 per person
$355
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
18/10 Exceptional! (1,128 reviews)
Quiet room-well located-

Reviewed on Nov 16, 2025

Coronado Beach Resort

Coronado Beach Resort

3 out of 5
Historic Downtown Coronado
Price was $1,244, price is now $684 per person
$684
per person
Jan 21 - Jan 28
found 1 day ago
Roundtrip flight included
Denver (DEN) to San Diego (SAN)
9/10 Wonderful! (734 reviews)
We absolutely loved our stay at the Coronado Beach Resort! The location is unbeatable — just a block from a gorgeous beach and close to everything in San Diego. The staff are wonderfully friendly and helpful, and the amenities are fantastic: beach wagons, chairs, umbrellas, pool, ping pong, board games, DVD rentals, and even Ms. Cody, the resident parrot who greets you in the lobby. The rooftop BBQs, hot tub, and sauna with sunset views were highlights of our stay. We didn’t realize until we arrived that it’s a timeshare property, but there was no sales pitch at all — just a warm, relaxed atmosphere. Many guests are longtime regulars who clearly know each other and the staff, which adds to the welcoming, community feel. We’re not owners, but we felt completely at home here. It’s a true gem — we’d happily stay here again and would definitely recommend it to anyone visiting Coronado!

Reviewed on Nov 12, 2025

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

3 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

Hotel del Coronado, Curio Collection by Hilton

Hotel del Coronado, Curio Collection by Hilton

4 out of 5
1500 Orange Ave Coronado CA
Fully refundableReserve now, pay when you stay
$377 nightly
The price is $419 total per night from Nov 25 to Nov 26
$419 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Hotel and room were very clean! The hotel staff were very accommodating. The most beautiful hotel with so much history! I absolutely love this place!!

Reviewed on Nov 15, 2025

Hotel del Coronado, Curio Collection by Hilton
Legacy Resort Hotel & Spa

Legacy Resort Hotel & Spa

4 out of 5
875 Hotel Circle South San Diego CA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $206 total per night from Nov 23 to Nov 24
$206 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (2,929 reviews)
Weekend getaway at this beautiful property was just what i needed defiantly will recommend 10/10

Reviewed on Nov 14, 2025

Legacy Resort Hotel & Spa
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 24 to Nov 25
$131 total
Nov 24 - Nov 25
Total with taxes and fees
8/10 Very Good! (2,178 reviews)
Staff was very friendly and helpful.

Reviewed on Nov 16, 2025

Hilton San Diego Mission Valley
See all 8,509 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

$57
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

$95
per adult
94% of travellers recommend
San Diego Old Town Trolley Hop-On Hop-Off Tour
Great Scenery

San Diego Sunset Cruise from Mission Bay

$40
per adult
78% of travellers recommend
San Diego Sunset Cruise from Mission Bay
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.