Calimesa Vacations from $331

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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.
Sands Motel
Bluegreen Vacations Big Bear Village, an Ascend Collection Resort
Empire Inn
A-frame Retreat Chic and Modern Forest Views, Hammock, Outdoor Dining, Decks
Hampton Inn & Suites Ontario
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What to do in Calimesa

Calimesa Hotel Deals

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
$213 nightly
The price is $241 total per night from Mar 23 to Mar 24
$241 total
Mar 23 - Mar 24
Total with taxes and fees
8.6/10 Excellent! (2,262 reviews)
Hotel is very beautiful and unique. Vallet parking was great. Restaurant waiter was inappropriate at times, front desk people were not very friendly and welcoming. Over all it’s worth to stay here for the history of its building and pool/spa was wonderful.

Reviewed on Mar 6, 2026

The Mission Inn Hotel & Spa
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
$99 nightly
The price is $109 total per night from Mar 15 to Mar 16
$109 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (2,715 reviews)
Great stay and location. Would definitely stay here again.

Reviewed on Mar 6, 2026

DoubleTree by Hilton Hotel San Bernardino
Lagonita Lodge

Lagonita Lodge

3 out of 5
183 Lagonita Ln Big Bear Lake CA
$90 nightly
The price is $102 total per night from Mar 15 to Mar 16
$102 total
Mar 15 - Mar 16
Total with taxes and fees
9/10 Wonderful! (4,123 reviews)
We've stayed here several times and at times for more than a week. The rooms are nice size and it's a great location. My pet peeve is that the dispensers in the shower (for shampoo ect) are always empty. Otherwise, it is a good value.

Reviewed on Mar 5, 2026

Lagonita Lodge
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 $331 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.