Chalk Hill Vacation Packages 2026 from $284

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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

$284

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (786 reviews)

Really enjoyed my stay! Very clean and extremely quiet. Hope to return soon!

Reviewed on Aug 16, 2026

The Sofia Hotel

Downtown San Diego

$298

per person

Oct 20 - Oct 23

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.6/10 Excellent! (2,462 reviews)

Le Bon Hotel Hollywood

Hollywood

$297

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (453 reviews)

I like that is close to subway

Reviewed on Aug 13, 2026

Hotel H-Wood

Hollywood

$307

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.2/10 (1,003 reviews)

No towels didn’t feel safe lock would unlock when tapped

Reviewed on Aug 15, 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 wineries.

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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 top-notch restaurants or wineries 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

$122 nightly

$139 total

Aug 23 - Aug 24

Total with taxes and fees

9.2/10 Wonderful! (1,334 reviews)

"Clean room. Breakfast was surprisingly good and my husband loved the morning that they had a cheese omelette and biscuits and gravy. They had a nice sauna and jacuzzi."

Reviewed on Aug 16, 2026

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA

Fully refundableReserve now, pay when you stay

$147 nightly

$168 total

Aug 23 - Aug 24

Total with taxes and fees

9.2/10 Wonderful! (1,003 reviews)

"It was very clean , good mattress"

Reviewed on Aug 15, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$239 nightly

$272 total

Aug 20 - Aug 21

Total with taxes and fees

See all 2,087 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.