Chalk Hill Vacation Packages 2026 from $254

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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

Save 100% on your flight

$254

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (868 reviews)

Very clean room

Reviewed on Sep 30, 2026

The Sofia Hotel

Downtown San Diego

$575

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.6/10 Excellent! (2,663 reviews)

Hotel is well situated in downtown San Diego and has on-site parking for a fee. Very nice hotel, has a really nice bar and the rooms are beautiful and clean.

Reviewed on Sep 30, 2026

Le Bon Hotel Hollywood

Hollywood

Save 100% on your flight

$362

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (496 reviews)

Paradise Point Resort & Spa

Mission Bay

Save 100% on your flight

$314

per person

Dec 8 - Dec 11

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.8/10 Excellent! (2,887 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

Save 100% on your flight

$328

per person

Nov 19 - Nov 21

found 8 hours ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8/10 Very Good! (1,007 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

$106 nightly

$121 total

Nov 1 - Nov 2

Total with taxes and fees

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$232 nightly

$264 total

Oct 27 - Oct 28

Total with taxes and fees

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$142 nightly

$161 total

Oct 27 - Oct 28

Total with taxes and fees

See all 2,057 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.