Chalk Hill Vacation Packages 2026 from $231

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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

$231

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (817 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

$421

per person

Oct 3 - Oct 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.2/10 Very Good! (1,012 reviews)

Encore Inn Inglewood

Lockhaven

$242

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.8/10 (24 reviews)

Le Bon Hotel Hollywood

Hollywood

$288

per person

Oct 3 - Oct 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (466 reviews)

Hotel H-Wood

Hollywood

$344

per person

Oct 1 - Oct 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.2/10 (1,007 reviews)

Great hotel! Will definitely stay there again!

Reviewed on Aug 29, 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

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$276 nightly

$314 total

Sep 1 - Sep 2

Total with taxes and fees

9.4/10 Exceptional! (1,960 reviews)

"Great place to stay. Excellent pool and hot tub."

Reviewed on Aug 30, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$142 nightly

$161 total

Sep 7 - Sep 8

Total with taxes and fees

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

3421 Cleveland Ave Santa Rosa CA

Fully refundable

$110 nightly

$127 total

Sep 21 - Sep 22

Total with taxes and fees

8.6/10 Excellent! (2,451 reviews)

"The pool/hot tub are really nice. The breakfast room is a rare surprise. Room was comfortable and clean. Worth the money we spent on the room."

Reviewed on Aug 29, 2026

See all 2,092 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.