Chalk Hill Vacation Packages 2026 from $286

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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

$286

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (786 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

$547

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.2/10 Very Good! (1,014 reviews)

The Sofia Hotel

Downtown San Diego

$797

per person

Sep 19 - Sep 25

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.6/10 Excellent! (2,428 reviews)

Staff was amazing. Rooms were comfortable. Only reason why i can’t give a 5 star review is because the TV didn’t really work. After a long day it would be nice to come back to a tv that has working channels instead of choppy signal or just not loading at all.

Reviewed on Aug 8, 2026

Le Bon Hotel Hollywood

Hollywood

$335

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (447 reviews)

Great place for the price

Reviewed on Aug 8, 2026

Glendale Hotel

Somerset

$303

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.4/10 Very Good! (3,348 reviews)

The check in was through a kiosk but the lady was nice.

Reviewed on Aug 8, 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 wineries.

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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

$118 nightly

$135 total

Sep 7 - Sep 8

Total with taxes and fees

9.2/10 Wonderful! (1,336 reviews)

"Very nice"

Reviewed on Aug 7, 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 16 - Aug 17

Total with taxes and fees

9.2/10 Wonderful! (1,014 reviews)

"Its usually good"

Reviewed on Aug 7, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$276 nightly

$314 total

Aug 9 - Aug 10

Total with taxes and fees

See all 2,088 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.