Chalk Hill Vacation Packages 2026 from $160

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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.

The LEEF Hotel

Citrus Grove

$160

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (829 reviews)

Would not recommend

Reviewed on Sep 14, 2026

The Sofia Hotel

Downtown San Diego

$441

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.6/10 Excellent! (2,586 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

$483

per person

Nov 18 - Nov 22

found 8 hours ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.2/10 Very Good! (1,006 reviews)

Le Bon Hotel Hollywood

Hollywood

$229

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (470 reviews)

The Westin St. Francis San Francisco on Union Square

Union Square

$509

per person

Nov 8 - Nov 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Francisco (SFO)

8.8/10 Excellent! (2,247 reviews)

The staff and service was amazing!

Reviewed on Sep 14, 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

$126 nightly

$144 total

Oct 13 - Oct 14

Total with taxes and fees

9.2/10 Wonderful! (1,324 reviews)

"Staff"

Reviewed on Sep 13, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$229 nightly

$261 total

Sep 27 - Sep 28

Total with taxes and fees

9.4/10 Exceptional! (1,987 reviews)

"We stayed the weekend for our anniversary and it was delightful! Place was clean, staff was very friendly and helpful. Their hot tub is open until 11 PM and we truly enjoyed taking a dip after dinner! Would stay again!"

Reviewed on Sep 13, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$138 nightly

$157 total

Sep 24 - Sep 25

Total with taxes and fees

9.4/10 Exceptional! (2,638 reviews)

"Great"

Reviewed on Sep 14, 2026

See all 2,040 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.