Diamond Lake Vacations from $285

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Your Diamond Lake Vacation

Enjoy amazing adventures when you book a vacation package to Diamond Lake. Whether you're a foodie, history buff or just a traveler who loves to see new places, there's something for everyone in this lively city. Fill your trip to Diamond Lake with tours of some of its big-hitting attractions. First stop? Make a beeline for Cat Ski Mt. Bailey. A couple of quick clicks is all it takes to put together the ultimate Diamond Lake vacation on Expedia.

The Latest Diamond Lake vacation packages

Price found within the past 48 hours. Click for updated prices.
Wine Country Inn

Wine Country Inn

3 out of 5
Price was $378, price is now $285 per person
$285
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
18.8/10 Exceptional! (1,002 reviews)
Cute comfy room. Just needed quick sleep to continue drive. Wish could have explored the town more. Did not try the breakfast but host provided hot water night before for tea. Very gracious hostess. Thanks again.

Reviewed on Nov 14, 2025

Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $820, price is now $599 per person
$599
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
19.6/10 Exceptional! (257 reviews)
Beautiful room with comfortable bed. Nice quality bedding.

Reviewed on Oct 26, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $468, price is now $369 per person
$369
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
19.2/10 Exceptional! (1,003 reviews)
Great Staff, cozy room, comfy bed and pillows. Over looking the pool was a plus. Foid and drinks were top notch.

Reviewed on Nov 20, 2025

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $408, price is now $322 per person
$322
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
18/10 Exceptional! (1,497 reviews)
Excellent stay. We would go there again.

Reviewed on Nov 22, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $491, price is now $394 per person
$394
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Medford (MFR)
18.4/10 Exceptional! (1,000 reviews)
Front desk staff made me feel welcome and were very helpful!!!

Reviewed on Nov 18, 2025

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Discover the most popular places to visit in Diamond Lake

Cat Ski Mt. Bailey

Hit the slopes in Diamond Lake with a visit to Cat Ski Mt. Bailey. While you're in the area, stroll along the lakeside.

Cat Ski Mt. Bailey

Diamond Lake Hotel Deals

Dawson House Lodge

Dawson House Lodge

2.5 out of 5
109455 Hwy 97 North Chemult OR
Fully refundable
$119 nightly
The price is $130 total per night from Nov 25 to Nov 26
$130 total
Nov 25 - Nov 26
Total with taxes and fees
7/10 Good! (595 reviews)
Great for the price and close to Crater Lake National Park.

Reviewed on Nov 6, 2025

Dawson House Lodge
Eagle Crater Lake Inn

Eagle Crater Lake Inn

2.5 out of 5
108915 U.S. 97 Chemult OR
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $140 total per night from Nov 24 to Nov 25
$140 total
Nov 24 - Nov 25
Total with taxes and fees
7.4/10 Good! (736 reviews)
The host is super helpful. I had an issue with my car and he went above and beyond to fix it.

Reviewed on Oct 8, 2025

Eagle Crater Lake Inn
See all 3 properties in Diamond Lake
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 Diamond Lake Vacation Packages

Diamond Lake Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
35ºF
Max Temp Summer
70ºF
Top Sights
Pumice Desert, Cat Ski Mt. Bailey and Miller Lake

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Frequently asked questions

How much does a Diamond Lake vacation package cost?
You can snap up a vacation package to this popular destination from $285 on Expedia. However, how much your vacation to Diamond Lake costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Diamond Lake?
December, January and February are the best times to look for cheap Diamond Lake vacation packages. Traveling in quieter periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Diamond Lake?
With a well-organized itinerary, you can easily visit the main Diamond Lake attractions in a few days. But if you want to discover hidden spots or take day trips, think about booking your Diamond Lake vacation for longer.
How to find the best Diamond Lake package deals?
Start your search for a Diamond Lake package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Diamond Lake package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Diamond Lake adventure underway.
Is it cheaper to book a Diamond Lake vacation as a package?
You can enjoy significant savings on your Diamond Lake escape by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Diamond Lake?
If you've got your Diamond Lake travel dates confirmed, book as early as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Diamond Lake vacation packages?
Set off on your dream getaway to Diamond Lake with help from our Book Now, Pay Later vacations. No need to scrimp and save or hold off until the next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily budget for your trip and snap up bargains while they last.

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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.