Chalk Hill Vacation Packages 2026 from $238

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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.

Encore Inn Inglewood

Lockhaven

$238

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.6/10 (196 reviews)

The Sofia Hotel

Downtown San Diego

$618

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.6/10 Excellent! (2,462 reviews)

Paradise Point Resort & Spa

Mission Bay

$1,355

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.8/10 Excellent! (2,774 reviews)

Le Bon Hotel Hollywood

Hollywood

$290

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.4/10 Good! (460 reviews)

Staff was super helpful and even called me to let me know another room opened up for my friends. Will be back! 5

Reviewed on Aug 22, 2026

The Westin St. Francis San Francisco on Union Square

Union Square

Save 100% on your flight

$541

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Francisco (SFO)

8.8/10 Excellent! (2,267 reviews)

There was food left in the fridge from idk when or how long. They need to talk to there house keeper to make sure to clean the bath sink was dirty with people before us makeup in the sink. Did like how security followed me and my sister because we had hoodies on making it seem like we didn’t belong there no happy with my stay

Reviewed on Aug 24, 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

$237 nightly

$271 total

Aug 26 - Aug 27

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

Sep 7 - Sep 8

Total with taxes and fees

9.4/10 Exceptional! (2,620 reviews)

"Location is close to the casino"

Reviewed on Aug 24, 2026

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! (2,475 reviews)

"Clean hotel close to the airport. We will definitely stay there again."

Reviewed on Aug 23, 2026

See all 2,097 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.