Calimesa Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

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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
The price is CA $150 per night from Jul 27 to Jul 28
CA $150
CA $165 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (3,086 reviews)
"Nice location, nice staff, the room just smelled like smoke when we checked in so we had to get another one. That room was fine."

Reviewed on Jul 10, 2026

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
The price is CA $245 per night from Jul 26 to Jul 27
CA $245
CA $316 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,398 reviews)
"There is something for every age! We came with four adults and four kids all different ages and had the best time! Love the game room, movie room, lake and pool area. Sitting outside having a bonfire and making s’mores makes the trip the perfect escape we all were looking forward to. We come every ..."

Reviewed on Jul 10, 2026

Lake Arrowhead Resort and Spa
Quality Inn Riverside near UCR and Downtown

Quality Inn Riverside near UCR and Downtown

2.5 out of 5
1590 University Ave Riverside CA
Fully refundable
The price is CA $134 per night from Aug 10 to Aug 11
CA $134
CA $151 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,405 reviews)
"This is a rundown hotel. The bathroom shower didn't work, and the curtain was falling."

Reviewed on Jul 7, 2026

Quality Inn Riverside near UCR and Downtown
See all 4,844 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Calimesa

Rancho Cucamonga: Escape Room Adventure Game

Rancho Cucamonga: Escape Room Adventure Game

CA $61
per adult
Rancho Cucamonga: Escape Room Adventure Game
Magical Golden Hour Mural Tour Downtown Ontario Arts District

Magical Golden Hour Mural Tour Downtown Ontario Arts District

CA $78
per adult
Magical Golden Hour Mural Tour Downtown Ontario Arts District
Family-Friendly Nature Hike around the Big Bear Valley

Family-Friendly Nature Hike around the Big Bear Valley

CA $52
per adult
100% of travellers recommend
Family-Friendly Nature Hike around the Big Bear Valley
See all activities in Calimesa

Frequently asked questions

How much does a Calimesa vacation package cost?
You'll find cheap prices on Expedia for your Calimesa getaway. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Calimesa costs.
What are the cheapest months to go to Calimesa?
January, July and August are great times to look for cheap Calimesa vacation packages. Opting to travel in less busy months means you can typically find reduced prices on hotels and flights.
How many days is enough for Calimesa?
Generally, a handful of days is great for a Calimesa vacation. With a well-planned itinerary, you can go to all the best sights such as Edward-Dean Museum of Decorative Arts, as well as discover some hidden gems along the way.
How to find the best Calimesa package deals?
Begin your search for a Calimesa package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Calimesa package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Calimesa adventure underway.
Is it cheaper to book a Calimesa vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels separately. Better still, you can customize your Calimesa escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Calimesa?
If you're considering an impromptu Calimesa adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Calimesa?

  1. Pick your dates: The things you plan to do in Calimesa and your favourite season can help you decide when to get away.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Calimesa. Then, pick a property that suits your budget, whether that's a low-cost option or a high-end retreat.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you want to get to in Calimesa. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Calimesa vacation package for you.

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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.