Chalk Hill Vacation Packages 2026 from $298

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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

$298

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

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

Meh

Reviewed on Oct 18, 2026

Big Bear Spa Suites

$2,330

per person

Dec 20 - Dec 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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

Glendale Hotel

Somerset

$380

per person

Dec 8 - Dec 14

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.4/10 Very Good! (3,497 reviews)

По

Reviewed on Oct 18, 2026

The LEEF Hotel

Citrus Grove

$331

per person

Dec 8 - Dec 14

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.6/10 Excellent! (879 reviews)

Malibu Country Inn

Central Malibu

Save 100% on your flight

$393

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.8/10 Good! (1,007 reviews)

great location, peaceful, quiet and beautiful! has sea and mountain views. Staff was helpful and friendly. Our room had no phones, broken blinds, no hot water heating kettle and a leaking fridge, was not cleaned inside. Balcony was not cleaned. We had to check out early, just one day: due to flood warnings and coastal high waves. But the hotel refused to refund the money. very bad. Hotels .com does not help either. Has good parking and good view, great location.

Reviewed on Oct 17, 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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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

$110 nightly

$125 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,306 reviews)

"Frankly I was surprised at how nice the hotel was. Nothing fancy but very good. Solid hot/cold breakfast. Great location!"

Reviewed on Oct 17, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$283 nightly

$322 total

Nov 18 - Nov 19

Total with taxes and fees

9.4/10 Exceptional! (2,059 reviews)

"The front desk staff were very polite and helpful. Our dinner waiter was superb. I would recommend that all dining tables have some light at the table. Ours had none. In all a great stay!"

Reviewed on Oct 18, 2026

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$136 nightly

$156 total

Nov 16 - Nov 17

Total with taxes and fees

See all 2,059 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.