Chalk Hill Vacation Packages 2026 from $176

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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.

Hollywood Inn Suites Hotel

Save 100% on your flight

$176

per person

Dec 12 - Dec 15

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.4/10 Very Good! (2,105 reviews)

Love it

Reviewed on Oct 17, 2026

Big Bear Spa Suites

$2,330

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

$357

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

The Westin St. Francis San Francisco on Union Square

Union Square

Save 100% on your flight

$579

per person

Nov 29 - Dec 3

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Francisco (SFO)

8.8/10 Excellent! (2,195 reviews)

It was great. Westin’s always get the job done. Impressed with the updates and new restaurant inside!

Reviewed on Oct 16, 2026

Glendale Hotel

Somerset

Save 100% on your flight

$698

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

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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

$103 nightly

$117 total

Nov 15 - Nov 16

Total with taxes and fees

9.2/10 Wonderful! (1,305 reviews)

"We had plumbing issues with sink and bathtub. Other then that our stay was great. We would comeback again"

Reviewed on Oct 15, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$339 nightly

$386 total

Nov 16 - Nov 17

Total with taxes and fees

9.4/10 Exceptional! (2,058 reviews)

"Would highly recommend"

Reviewed on Oct 17, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$136 nightly

$156 total

Nov 16 - Nov 17

Total with taxes and fees

9.4/10 Exceptional! (2,722 reviews)

"We stayed here for a nearby wedding. The price was a bit better than others near. We did get a surprise when we checked in as we were not told, even when we paid our stay in advance, that they also needed a $200.00 deposit. Not sure why they didn’t add that to the prepayment. Got our room and when ..."

Reviewed on Oct 17, 2026

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.