Chalk Hill Vacation Packages 2026 from $372

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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.

SIRTAJ - Beverly Hills

South of Wilshire

Save 100% on your flight

$372

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

Good price and location. Room was clean. No door to bathroom, so not private. Parking was a bit of a fiasco and we got locked inside garage. Staff was pleasant except for person who checked us out. Very short to us. Recommend overall

Reviewed on Sep 9, 2026

The Sofia Hotel

Downtown San Diego

$758

per person

Nov 11 - Nov 15

found 5 hours ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.6/10 Excellent! (2,586 reviews)

Great historic property. Definitely has character. We enjoyed our stay. Clean, quiet and fairly centrally located for San Diego.

Reviewed on Sep 10, 2026

The Grove Inn

Western Addition

Save 100% on your flight

$765

per person

Oct 20 - Oct 25

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Francisco (SFO)

9.2/10 Wonderful! (735 reviews)

The Historic Broadlind Hotel at Long Beach Convention Center

Downtown Long Beach

$685

per person

Oct 28 - Nov 4

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (957 reviews)

Kitchen is very nice

Reviewed on Aug 23, 2026

Gjelina Hotel

Save 100% on your flight

$451

per person

Nov 12 - Nov 16

found 2 hours ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

9.6/10 Exceptional! (97 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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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

$127 nightly

$145 total

Sep 13 - Sep 14

Total with taxes and fees

9.2/10 Wonderful! (1,322 reviews)

"Room was nice, clean and they were able to accommodate the first floor. Very comfortable pillows - (meant to ask where I could buy a couple!). Pool area was okay - hot spa was nice and warm. Breakfast was basic, not the best, but not the worst we've ever had."

Reviewed on Sep 9, 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

Sep 20 - Sep 21

Total with taxes and fees

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$226 nightly

$258 total

Sep 27 - Sep 28

Total with taxes and fees

9.4/10 Exceptional! (1,972 reviews)

"Lovely spot"

Reviewed on Sep 9, 2026

See all 2,078 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.