Chalk Hill Vacation Packages 2026 from $283

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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.

Le Bon Hotel Hollywood

Hollywood

Save 100% on your flight

$283

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.4/10 Good! (507 reviews)

The Sofia Hotel

Downtown San Diego

$286

per person

Dec 8 - Dec 11

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.6/10 Excellent! (2,663 reviews)

Good!

Reviewed on Oct 2, 2026

Hotel H-Wood

Hollywood

Save 100% on your flight

$294

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

6.2/10 (1,003 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

Save 100% on your flight

$354

per person

Nov 19 - Nov 21

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8/10 Very Good! (1,016 reviews)

Two short blocks away from the Beverly Wilshire Hotel featured in the 80's movie "Pretty Woman." The SIRTAJ is centrally located to many restaurants and shops. Tiffany & Co., Fendi, Chanel, Spago, etc. The SIRTAJ is located directly across from Reeves Park and an underground parking garage.

Reviewed on Oct 2, 2026

Glendale Hotel

Somerset

Save 100% on your flight

$438

per person

Dec 23 - Dec 28

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.4/10 Very Good! (3,471 reviews)

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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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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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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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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

$106 nightly

$121 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,304 reviews)

"Nice stay. Clean, comfortable, and great breakfast!"

Reviewed on Oct 2, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$297 nightly

$338 total

Oct 5 - Oct 6

Total with taxes and fees

9.4/10 Exceptional! (2,016 reviews)

"Exactly as described"

Reviewed on Oct 3, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$142 nightly

$161 total

Oct 21 - Oct 22

Total with taxes and fees

9.4/10 Exceptional! (2,677 reviews)

"I like everything about this hotel. My only complaint was the breakfast. Food was ok and on a good note the staff in the restaurant were very nice. Other than that, everything is good and I will be coming back."

Reviewed on Oct 3, 2026

See all 2,060 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.