Calimesa Vacations from $268

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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.
Delta Hotels by Marriott Ontario Airport

Delta Hotels by Marriott Ontario Airport

3 out of 5
Racimo
Price was $565, price is now $268 per person
$268
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Ontario (ONT)
9/10 Wonderful! (173 reviews)
The room was great, but I purchased the room because it came with breakfast, I had no proof, and I was charged 40.00 . Plus parking fees 17.00. It just shocked me.

Reviewed on Nov 4, 2025

N+P Boutique Lodge

N+P Boutique Lodge

4 out of 5
Save 100% on your flight
Price was $1,926, price is now $1,180 per person
$1,180
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Ontario (ONT)
19.6/10 Exceptional! (203 reviews)
Beautiful cabin! Great quiet location

Reviewed on Nov 16, 2025

Holiday Inn Express & Suites Loma Linda- San Bernardino S by IHG

Holiday Inn Express & Suites Loma Linda- San Bernardino S by IHG

2.5 out of 5
Save 100% on your flight
Price was $554, price is now $391 per person
$391
per person
Jan 1 - Jan 8
found 4 hours ago
Roundtrip flight included
Denver (DEN) to Ontario (ONT)
8.8/10 Excellent! (1,013 reviews)
Room was very clean. Staff was very friendly

Reviewed on Nov 15, 2025

SoCal Vacations - Village Inn

SoCal Vacations - Village Inn

2.5 out of 5
Big Bear Central
Save 100% on your flight
Price was $916, price is now $690 per person
$690
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Ontario (ONT)
18.4/10 Exceptional! (287 reviews)
The kitchen was stocked with all the dishes and utensils to make breakfast, lunch and dinner. The location of the unit was in walking distance to any restaurant, bar or hiking trail.

Reviewed on Nov 14, 2025

Tahquitz Pines Retreat

Tahquitz Pines Retreat

2 out of 5
Price was $475, price is now $367 per person
$367
per person
Feb 8 - Feb 14
found 8 hours ago
Roundtrip flight included
Seattle (SEA) to Ontario (ONT)
19.2/10 Exceptional! (1,278 reviews)
We arrived at 2pm with a pre-check through Expedia but our room was not ready until shortly after 5pm. We also asked for a downstairs unit and we were upstairs. Not happy with the checkin experience however our room was clean and it was quiet and we enjoyed our stay. Hopefully our next check in experience will be better.

Reviewed on Nov 14, 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
$93 nightly
The price is $103 total per night from Nov 28 to Nov 29
$103 total
Nov 28 - Nov 29
Total with taxes and fees
8.6/10 Excellent! (2,404 reviews)
Great value. The biggest downside was the heating unit was very loud when it would come on.

Reviewed on Nov 16, 2025

DoubleTree by Hilton Hotel San Bernardino
Studio 6 Suites Perris, CA

Studio 6 Suites Perris, CA

2 out of 5
480 S Redlands Ave Perris CA
Fully refundableReserve now, pay when you stay
$58 nightly
The price is $64 total per night from Nov 20 to Nov 21
$64 total
Nov 20 - Nov 21
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
Clean room, new, good parking, close to freeway, gas, mini mart, Jack in the box. Denny's.

Reviewed on Nov 12, 2025

Studio 6 Suites Perris, CA
Lagonita Lodge

Lagonita Lodge

3 out of 5
183 Lagonita Ln Big Bear Lake CA
$102 nightly
The price is $115 total per night from Nov 20 to Nov 21
$115 total
Nov 20 - Nov 21
Total with taxes and fees
9/10 Wonderful! (3,950 reviews)
Location and amenities

Reviewed on Nov 13, 2025

Lagonita Lodge
See all 4,806 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 $268 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.