Chalk Hill Vacation Packages 2026 from $275

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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

$275

per person

Oct 26 - Oct 31

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (767 reviews)

The Sofia Hotel

Downtown San Diego

$665

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)

Room was clean and comfortable. Staff were friendly and helpful. We loved the coffee and breakfast at the restaurant.

Reviewed on Aug 6, 2026

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)

There was no one at the desk when I arrived. No hot water the first morning. When I called about it, the front desk person was like “oh well, I’ll report it to maintenance.” For what I paid, they should have moved me to a different room immediately. But they did not care. I guarantee that I won’t be returning.

Reviewed on Aug 5, 2026

Hollywood Inn Suites Hotel

$804

per person

Sep 10 - Sep 15

found 23 hours ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.4/10 Very Good! (1,961 reviews)

The reception made the hotel so bad,

Reviewed on Aug 7, 2026

Claremont Resort & Club

Claremont Hills

$1,132

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Denver (DEN) to Oakland (OAK)

9/10 Wonderful! (1,058 reviews)

Effie was amazing!! The room was roomy and the restaurant was great!

Reviewed on Aug 5, 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

$122 nightly

$139 total

Aug 23 - Aug 24

Total with taxes and fees

9.2/10 Wonderful! (1,335 reviews)

"Beds are really comfortable and shower nice. Needed more towels though. Wish they had a complete restaurant though."

Reviewed on Aug 3, 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! (1,013 reviews)

"We were so impressed with how nice this place is! Room was really nice we enjoyed the pool and hot tub only down size was the noise of the highway!"

Reviewed on Aug 6, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$279 nightly

$318 total

Aug 16 - Aug 17

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.