Chalk Hill Vacation Packages 2026 from $266

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Your Chalk Hill Vacation

With a Chalk Hill vacation package, you can forget about planning hassles and simply focus on experiencing all this exciting destination has to offer. Not sure where to stay? Windsor is one of the most popular cities to explore during a trip to Chalk Hill. Whether you're traveling for a couple of days or a couple of weeks, Expedia are here to help you customize your next Chalk Hill vacation.

The Latest Chalk Hill vacation packages

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

Glendale Hotel

Somerset

Save 100% on your flight

$266

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.4/10 Very Good! (3,497 reviews)

They have a virtual front desk, so there is no front desk with a person behind it. No bathroom in the lobby either. The property is very antiquated, dark and dirty. I’ll never be back.

Reviewed on Oct 19, 2026

Big Bear Spa Suites

$2,294

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Los Angeles (LAX)

8.2/10 Very Good! (350 reviews)

This place was so comfy and cozy, the bed was so comfortable and the spa in the room was amazing. We loved it and will definitely stay here again.

Reviewed on Oct 7, 2026

SIRTAJ - Beverly Hills

South of Wilshire

$298

per person

Dec 11 - Dec 14

found 2 days ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8/10 Very Good! (1,016 reviews)

Meh

Reviewed on Oct 18, 2026

Fleur Noire Hotel - 21 and Over

Uptown Design District

Save 100% on your flight

$600

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

9.6/10 Exceptional! (1,003 reviews)

We loved our stay at Fleur Noir. It is a quirky little place with plenty of charm. We have to shout out Bree who goes above and beyond and is a ray of sunshine!

Reviewed on Oct 16, 2026

Delos Reyes Palm Springs

Save 100% on your flight

$2,420

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)

7.6/10 Good! (1,477 reviews)

This is the second time I've stayed at this hotel, the price is reasonable for the room and pool access, staff is very friendly

Reviewed on Oct 5, 2026

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Stay near popular Chalk Hill attractions

Safari West

8.8/10 (257 reviews)

Explore the lovely green spaces of Safari West and also enjoy the biking trails in Santa Rosa. Amble around this romantic area's riverfront and enjoy its top-notch restaurants.

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Chalk Hill Estate Vineyard

8.4/10 (12 reviews)

You can enjoy a tasting or tour at Chalk Hill Estate Vineyard during your travels to Healdsburg. Stroll along the area's riverfront, or simply savor its top-notch restaurants.

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Windsor Oaks Vineyards

9.6/10 (5 reviews)

You can enjoy a tasting or tour at Windsor Oaks Vineyards during your travels to Windsor. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

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Guerro Fernandez

You can enjoy a tasting or tour at Guerro Fernandez during your travels to Windsor. Check out the wineries or top-notch restaurants in this family-friendly area.

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Chalk Hill Hotel Deals

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane Windsor CA

Fully refundable

$107 nightly

$122 total

Nov 19 - Nov 20

Total with taxes and fees

9.2/10 Wonderful! (1,306 reviews)

"Frankly I was surprised at how nice the hotel was. Nothing fancy but very good. Solid hot/cold breakfast. Great location!"

Reviewed on Oct 17, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$283 nightly

$322 total

Nov 18 - Nov 19

Total with taxes and fees

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$140 nightly

$159 total

Nov 5 - Nov 6

Total with taxes and fees

See all 2,059 properties in Chalk Hill

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.