Chalk Hill Vacation Packages 2026 from $255

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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.

Kawada Hotel

Downtown Los Angeles

$255

per person

Oct 20 - Oct 23

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

The Sofia Hotel

Downtown San Diego

$758

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.6/10 Excellent! (2,586 reviews)

Parking was safe but surprising as surface level only. Staff was nice. Room was dated and not great in comparison to options in our timeframe. Free drink does not really cover for it.

Reviewed on Sep 11, 2026

The LEEF Hotel

Citrus Grove

Save 100% on your flight

$424

per person

Nov 20 - Nov 27

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (829 reviews)

SIRTAJ - Beverly Hills

South of Wilshire

$376

per person

Oct 20 - Oct 23

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

Le Bon Hotel Hollywood

Hollywood

Save 100% on your flight

$472

per person

Nov 20 - Nov 27

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (470 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 20 - Sep 21

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

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$226 nightly

$258 total

Sep 21 - Sep 22

Total with taxes and fees

9.4/10 Exceptional! (1,977 reviews)

"The room was nice. The staff was great. We will be going back."

Reviewed on Sep 11, 2026

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! (2,630 reviews)

"I understand that there might be lots of rooms to clean but check in time in MOST places is at 3pm. Here it's at 4pm but wasn't able to obtain my key until 5 pm. Rep mentioned he will contact me when my room was ready, never received a call nor text. Least they can do is extend check out time or ..."

Reviewed on Sep 10, 2026

See all 2,097 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.