Chalk Hill Vacation Packages 2026 from $262

Photo by Rick Alvarez

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

$262

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.6/10 (196 reviews)

The Sofia Hotel

Downtown San Diego

$348

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.6/10 Excellent! (2,462 reviews)

Location was good for exploration

Reviewed on Aug 14, 2026

Stanford Court San Francisco

Downtown San Francisco

Save 100% on your flight

$283

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Francisco (SFO)

9/10 Wonderful! (1,542 reviews)

We truly enjoyed our stay and will be returning customers!

Reviewed on Aug 14, 2026

Le Bon Hotel Hollywood

Hollywood

$328

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

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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

$115 nightly

$131 total

Sep 13 - Sep 14

Total with taxes and fees

9.2/10 Wonderful! (1,332 reviews)

"Staff was great! My sole complaint about our stay was that the bathroom lacked a fan. The room became musty after showers and this triggered my asthma and made it difficult for me to sleep and difficultto relax on a weekendaway, celebrating my birthday. Also, the pool and hot tub were out of order. ..."

Reviewed on Aug 13, 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

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$237 nightly

$271 total

Aug 16 - Aug 17

Total with taxes and fees

9.4/10 Exceptional! (1,933 reviews)

"We couldn't have found a better place fro stay at Bodega Bat. No complaints to speak of except that another grab bar in the shower would help us partially handicapped folks. The fireplace is a nice touch and we had NO problems with the TV,which was another pleasant surprise."

Reviewed on Aug 15, 2026

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.