Chalk Hill Vacation Packages 2026 from $251

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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

$251

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.4/10 (30 reviews)

The Sofia Hotel

Downtown San Diego

$803

per person

Nov 5 - Nov 12

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.6/10 Excellent! (2,550 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

$492

per person

Oct 3 - Oct 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.2/10 Very Good! (1,012 reviews)

👎

Reviewed on Sep 1, 2026

Hotel H-Wood

Hollywood

$372

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.2/10 (1,015 reviews)

This place is a freaking dump . Rude night staff and I never got the room I paid for. They moved we d me to the drug addict side of the budget inn instead and downsized my room to a one bedroom

Reviewed on Sep 1, 2026

Le Bon Hotel Hollywood

Hollywood

$358

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (466 reviews)

Don’t listen to the negative reviews this was a great stay for the money. Bed was comfy, room was clean, price was nice. No creamer for the coffee in the morning but whatever go get Starbucks yo lol.

Reviewed on Sep 2, 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

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA

Fully refundableReserve now, pay when you stay

$143 nightly

$163 total

Sep 9 - Sep 10

Total with taxes and fees

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$233 nightly

$265 total

Sep 3 - Sep 4

Total with taxes and fees

9.4/10 Exceptional! (1,956 reviews)

"The view on the bay and the ocean was splendid the room was immaculate and in addition we can see some very nice cows on the nearby field. The breakfast brought to the room was great both for the food and the kindness of the people, we will be back!"

Reviewed on Sep 2, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$137 nightly

$156 total

Sep 28 - Sep 29

Total with taxes and fees

9.4/10 Exceptional! (2,618 reviews)

"Muy buen hotel"

Reviewed on Sep 2, 2026

See all 2,092 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.