Calimesa Vacations from $295

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Your Calimesa Vacation

Get ready to experience Calimesa your way with a custom Calimesa vacation package! Uncovering the treasures of this interesting city is easier with a base in a neighborhood such as Downtown Redlands, which is great for history, among plenty of other things. Fill your free time with visits to Oak Valley Golf Club, East Valley Golf Club and San Timoteo Canyon, some of the attractions you should see during a trip to Calimesa. Your Calimesa vacation is only clicks away. Explore flights, accommodations and more on Expedia for an adventure that's tailored just for you.

The Latest Calimesa vacation packages

Price found within the past 48 hours. Click for updated prices.
Travel Inn And Suites

Travel Inn And Suites

2.5 out of 5
Old Town
Price was $449, price is now $295 per person
$295
per person
Feb 19 - Feb 23
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ontario (ONT)
4.4/10 (209 reviews)
Very sketchy outside and surprise 40 dollar deposit. Once in room I was good for night,clean room, hot shower, cable tv

Reviewed on Jan 2, 2025

Holiday Inn Victorville by IHG

Holiday Inn Victorville by IHG

3 out of 5
Civic Center
Save 100% on your flight
Price was $637, price is now $394 per person
$394
per person
Mar 5 - Mar 12
found 4 hours ago
Roundtrip flight included
Seattle (SEA) to Ontario (ONT)
8.2/10 Very Good! (1,000 reviews)
Room was nice and clean. Bed was comfortable. TV and cable was easy to use lots of channels to choose from. Water in shower doesn't get to hot, but pressure is good. Staff was friendly. Recommendation: There should be a menu from the café in the room.

Reviewed on Dec 14, 2025

@Marbella Lane - Serene Haven Retreat

@Marbella Lane - Serene Haven Retreat

3 out of 5
Save 100% on your flight
Price was $739, price is now $523 per person
$523
per person
Feb 4 - Feb 9
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Ontario (ONT)
No reviews
Marriott Riverside at the Convention Center

Marriott Riverside at the Convention Center

3.5 out of 5
Downtown Riverside
Price was $656, price is now $482 per person
$482
per person
Feb 17 - Feb 21
found 4 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Ontario (ONT)
8.6/10 Excellent! (1,002 reviews)
Everything was professional and comfortable

Reviewed on Dec 18, 2025

Courtyard by Marriott Riverside UCR/Moreno Valley Area

Courtyard by Marriott Riverside UCR/Moreno Valley Area

3 out of 5
Eastside
Price was $492, price is now $368 per person
$368
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ontario (ONT)
8.4/10 Very Good! (999 reviews)
It was a stone groove my man! Everything was in the fast lane, the staff was super groodalicious, the water was hot the facility was squeaky clean, the coffee was fresh, and the room was spotless. BUT the bed was uncomfortable and made for two nights of no sleep. We get the hotel room to sleep in and unfortunately we just were not able to do it. Thank you for great and friendly experience with the staff though, and having a clean pad for us to relax in though.

Reviewed on Dec 16, 2025

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Discover the most popular places to visit in Calimesa

Sunday race day at Glen Helen

Glen Helen Raceway

5/5(4 reviews)

You can take time to visit Glen Helen Raceway during your travels to San Bernardino. Stroll along the lakeside or discover the area's mountain views.

Glen Helen Raceway
Beautiful snow covered backdrop here in Fontana and it’s time for the Xfiniity Race.

Auto Club Speedway

4/5(70 reviews)

Catch an event at Auto Club Speedway during your trip to Fontana. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Auto Club Speedway

National Orange Show Events Center

4/5(308 reviews)

Catch an event at National Orange Show Events Center during your trip to San Bernardino. Visit the area's shops or amble around its riverfront.

National Orange Show Events Center

What to do in Calimesa

Rancho Cucamonga: Escape Room Adventure Game

Rancho Cucamonga: Escape Room Adventure Game

$43
per adult
Rancho Cucamonga: Escape Room Adventure Game
Family-Friendly Nature Hike around the Big Bear Valley

Family-Friendly Nature Hike around the Big Bear Valley

$37
per adult
100% of travellers recommend
Family-Friendly Nature Hike around the Big Bear Valley
See all activities in Calimesa

Calimesa Hotel Deals

DoubleTree by Hilton Hotel San Bernardino

DoubleTree by Hilton Hotel San Bernardino

4 out of 5
285 E Hospitality Lane San Bernardino CA
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Jan 18 to Jan 19
$108 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
8.6/10 Excellent! (2,484 reviews)
Breakfast was great. Staff friendly and helpful

Reviewed on Dec 16, 2025

DoubleTree by Hilton Hotel San Bernardino
Lake Arrowhead Resort and Spa

Lake Arrowhead Resort and Spa

3.5 out of 5
27984 Highway 189 Lake Arrowhead CA
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $171 total per night from Jan 4 to Jan 5
$171 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,140 reviews)
Close to the action

Reviewed on Dec 12, 2025

Lake Arrowhead Resort and Spa
The Mission Inn Hotel & Spa

The Mission Inn Hotel & Spa

4 out of 5
3649 Mission Inn Ave Riverside CA
Fully refundableReserve now, pay when you stay
$234 nightly
The price is $265 total per night from Jan 6 to Jan 7
$265 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
8.4/10 Very Good! (2,180 reviews)
Festival of Lights is fantastic

Reviewed on Dec 12, 2025

The Mission Inn Hotel & Spa
See all 4,881 properties in Calimesa
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.

Find the Best Calimesa Vacation Packages

Calimesa Essential Information

Language
English
Currency
U.S dollars
Closest Airport
San Bernardino, CA (SBD-San Bernardino Intl.)
Population
8,500
Max Temp Winter
60ºF
Max Temp Summer
90ºF
Top Sights
San Bernardino County Museum, Wildwood Canyon and Yucaipa Regional Park

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Frequently asked questions

How much does a Calimesa vacation package cost?
You'll find cheap prices from $295 on Expedia for your Calimesa break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Calimesa costs.
What are the cheapest months to go to Calimesa?
If you're hoping to score a cheap Calimesa vacation package, consider visiting in April, October and December. You're likely to find lower prices on accommodations and flights during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Calimesa?
The ideal length for your Calimesa vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to check out all the major attractions and explore some hidden treasures along the way.
How to find the best Calimesa package deals?
Finding a cheap Calimesa package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Calimesa package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Calimesa vacation as a package?
You can enjoy significant savings on your Calimesa escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Calimesa?
If you've got your Calimesa vacation dates finalized, book early to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Calimesa vacation packages?
Your Calimesa trip should be an escape from your busy life, not a reason for money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.