Chalk Hill Vacation Packages 2026 from $406

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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

$406

per person

Nov 6 - Nov 8

found 17 hours ago

Roundtrip flight included

Chicago (CHI) to Los Angeles (LAX)

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

Big Bear Spa Suites

$2,587

per person

Dec 22 - Dec 29

found 1 day ago

Roundtrip flight included

New York (NYC) to Los Angeles (LAX)

8.2/10 Very Good! (350 reviews)

Great

Reviewed on Aug 17, 2026

The Westin St. Francis San Francisco on Union Square

Union Square

Save 100% on your flight

$669

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to San Francisco (SFO)

8.8/10 Excellent! (2,195 reviews)

The scenery was beautiful

Reviewed on Oct 5, 2026

The Sofia Hotel

Downtown San Diego

Save 100% on your flight

$800

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Chicago (CHI) to San Diego (SAN)

8.6/10 Excellent! (2,663 reviews)

Beautiful 100 year old hotel. If you're looking for atmosphere and convenience for downtown San Diego, this is a great choice.

Reviewed on Oct 5, 2026

Pantai Inn

Village of La Jolla

Save 100% on your flight

$986

per person

Nov 13 - Nov 16

found 4 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to San Diego (SAN)

9.4/10 Exceptional! (1,003 reviews)

Location, location, location. We had a few hiccups when we checked in but the manager took care of it. Its an old place but its kept up fairly well. They provide free waters and soda and a different pitcher of infused water each day. Delicious! Breakfast is include. Pretty basic but all you really need. Would definitely stay again.

Reviewed on Sep 28, 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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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

$114 nightly

$130 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,305 reviews)

"The AC in the bedroom didn’t work. I notified the staff to see if it could be fixed in the morning. We came back in the late afternoon, still not working. So I asked again. This staff person checked and apparently it was broken and they were waiting for a replacement. No one thought to mention this ..."

Reviewed on Oct 3, 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 8 - Oct 9

Total with taxes and fees

9.4/10 Exceptional! (2,027 reviews)

"This is a charming place to stay with a huge room with great views. There was a fireplace and seating area as well. The bathroom was large and comfortable with good amenities. They left us a bottle of wine but no water. When I asked the front desk for a bottle they told me to buy it at the gas station. ..."

Reviewed on Oct 5, 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

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.