Chalk Hill Vacation Packages 2026 from $359

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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.

Hotel H-Wood

Hollywood

Save 100% on your flight

$359

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Los Angeles (LAX)

6.2/10 (1,008 reviews)

Okay for only sleeping

Reviewed on Sep 17, 2026

SIRTAJ - Beverly Hills

South of Wilshire

$548

per person

Nov 24 - Dec 1

found 15 hours ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.2/10 Very Good! (1,006 reviews)

I really enjoyed my stay here. The location cannot be beat. We quickly discovered it is much easier to take the stairs because the elevator is very slow but I would stay here again.

Reviewed on Sep 17, 2026

AKA Beverly Hills

Golden Triangle

$1,826

per person

Nov 24 - Dec 1

found 15 hours ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

9/10 Wonderful! (17 reviews)

The hotel offers a truly memorable stay, blending comfort with a distinct sense of character that sets it apart from standard accommodations. From the moment of arrival, the atmosphere feels warm and thoughtfully designed, with staff who are attentive without being overwhelming.

Reviewed on Jun 11, 2026

Kawada Hotel

Downtown Los Angeles

Save 100% on your flight

$522

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Los Angeles (LAX)

8.4/10 Very Good! (1,358 reviews)

Ice machine has a water dispenser next to it!

Reviewed on Sep 14, 2026

The Sofia Hotel

Downtown San Diego

Save 100% on your flight

$704

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.6/10 Excellent! (2,586 reviews)

The bar on-site, Truva, was lovely. Location is excellent. The lobby had a nostalgic noir vibe. Rooms are small but cozy. Ours had a single small window but that's just the way the hotel was built. Convenient sink outside the bathroom setup allowed one person to shower while the other could use the sink in the room.

Reviewed on Sep 18, 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 top-notch restaurants.

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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 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

$131 nightly

$149 total

Oct 4 - Oct 5

Total with taxes and fees

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$235 nightly

$268 total

Sep 20 - Sep 21

Total with taxes and fees

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$140 nightly

$160 total

Sep 24 - Sep 25

Total with taxes and fees

9.4/10 Exceptional! (2,645 reviews)

"Feels welcoming, pretty decent breakfast, clean and rooms are big."

Reviewed on Sep 18, 2026

See all 2,045 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.