Chalk Hill Vacation Packages 2026 from $367

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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.

Le Bon Hotel Hollywood

Hollywood

Save 100% on your flight

$367

per person

Dec 11 - Dec 14

found 2 hours ago

Roundtrip flight included

Atlanta (ATL) to Los Angeles (LAX)

7.4/10 Good! (507 reviews)

The Westin St. Francis San Francisco on Union Square

Union Square

$519

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to San Francisco (SFO)

8.8/10 Excellent! (2,219 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

$646

per person

Dec 8 - Dec 15

found 5 hours ago

Roundtrip flight included

Atlanta (ATL) to Los Angeles (LAX)

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

No amenities. Room was small

Reviewed on Oct 4, 2026

The Sofia Hotel

Downtown San Diego

$823

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to San Diego (SAN)

8.6/10 Excellent! (2,663 reviews)

1 Hotel West Hollywood

West Hollywood

Save 100% on your flight

$2,038

per person

Dec 8 - Dec 15

found 5 hours ago

Roundtrip flight included

Atlanta (ATL) to Los Angeles (LAX)

8.8/10 Excellent! (1,008 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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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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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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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

$114 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,305 reviews)

"The AC in the bedroom didn’t work. I notified the staff to see if it could be fixed in the morning. We came back in the late afternoon, still not working. So I asked again. This staff person checked and apparently it was broken and they were waiting for a replacement. No one thought to mention this ..."

Reviewed on Oct 3, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$297 nightly

$338 total

Oct 5 - Oct 6

Total with taxes and fees

9.4/10 Exceptional! (2,018 reviews)

"First off, the staff was extremely friendly. Everyone we had contact with was a pleasure to talk too. Our room was excellent. We chose dinner at the restaurant on the property. The decor was a bit dated, and it felt almost like something left over from the 70's. Our soup was luke warm, which was ..."

Reviewed on Oct 3, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$142 nightly

$161 total

Oct 21 - Oct 22

Total with taxes and fees

9.4/10 Exceptional! (2,686 reviews)

"Location and cleanliness"

Reviewed on Oct 4, 2026

See all 2,060 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.