Chalk Hill Vacation Packages 2026 from $258

Photo by Rick Alvarez

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.

LA Crystal Hotel - Los Angeles Area

Save 100% on your flight

$258

per person

Dec 3 - Dec 7

found 2 days ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (1,012 reviews)

room was clean and a has a great view! staff was very friendly and welcoming. Big variety of breakfast!

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

The Westin St. Francis San Francisco on Union Square

Union Square

Save 100% on your flight

$540

per person

Dec 1 - Dec 5

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

SIRTAJ - Beverly Hills

South of Wilshire

Save 100% on your flight

$563

per person

Dec 31 - Jan 3

found 1 day 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

$615

per person

Dec 31 - Jan 3

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

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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 17 - Nov 18

Total with taxes and fees

9.2/10 Wonderful! (1,307 reviews)

"Our experience was mostly very positive. The room was very clean and the bed was quite comfortable. My complaints are that the pool was too cold for an evening swim and the complimentary breakfast was not well maintained. We had to report to the desk that there were no eggs or biscuits. It took a ..."

Reviewed on Oct 19, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$318 nightly

$362 total

Nov 19 - Nov 20

Total with taxes and fees

9.4/10 Exceptional! (2,067 reviews)

"Our room was on the ground floor and we could hear people walking around on the floor above us for hours. Walls were not well insulated either. Two tone paint in the bathroom with stucco finish, not a good look. Breakfast was good but you have to cross a busy road to get there. As we were in our ..."

Reviewed on Oct 19, 2026

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.