Chalk Hill Vacation Packages 2026 from $186

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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.

The LEEF Hotel

Citrus Grove

Save 100% on your flight

$186

per person

Dec 11 - Dec 14

found 2 days ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (879 reviews)

Big Bear Spa Suites

$2,685

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)

This place was so comfy and cozy, the bed was so comfortable and the spa in the room was amazing. We loved it and will definitely stay here again.

Reviewed on Oct 7, 2026

SIRTAJ - Beverly Hills

South of Wilshire

$288

per person

Dec 11 - Dec 14

just found

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

Hotel in the heart of Beverly Hills, decent prices, great A/C,super convenient location if you don't have a car, otherwise get ready to pay 50dls a night for parking. There are a few options but demands a lot of attention to your car.

Reviewed on Oct 6, 2026

Le Bon Hotel Hollywood

Hollywood

$249

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.4/10 Good! (507 reviews)

Avenue Motel

$547

per person

Nov 11 - Nov 17

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.6/10 Good! (8 reviews)

I loved everything about this place, really clean and helpful friendly staff. The price was great on top of it!! Will go back definitely.

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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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 8 - Nov 9

Total with taxes and fees

9.2/10 Wonderful! (1,299 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

$349 nightly

$398 total

Oct 11 - Oct 12

Total with taxes and fees

9.4/10 Exceptional! (2,033 reviews)

"FYI. Food at the Tides is good but be aware that the portions are huge. Maybe sharing would be my advise. Also try to pay thru your card not thru the hotel so the charges are clear."

Reviewed on Oct 8, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$139 nightly

$158 total

Oct 22 - Oct 23

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.