Chalk Hill Vacation Packages 2026 from $295

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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.

Cathedral Hill Hotel

Downtown San Francisco

Save 100% on your flight

$295

per person

Dec 2 - Dec 7

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Francisco (SFO)

7.2/10 Good! (741 reviews)

Friendly staff, rooms are very nice and clean and the free parking is an absolute added bonus, parking always available. I recommend this establishment.

Reviewed on Oct 19, 2026

SIRTAJ - Beverly Hills

South of Wilshire

Save 100% on your flight

$580

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8.2/10 Very Good! (1,005 reviews)

Difficile de rejoindre la réception au telephone Garage est facturé selon les nuits passés à l’hôtel même si on a pas eu d’auto pour tout notre séjour

Reviewed on Oct 23, 2026

Aqua Breeze Inn

Westside Santa Cruz

Save 100% on your flight

$871

per person

Jan 14 - Jan 19

found 9 hours ago

Roundtrip flight included

Seattle (SEA) to San Jose (SJC)

8.2/10 Very Good! (1,003 reviews)

Everything was great from check in to the end of the stay. Location is great, the room was clean and worked out perfect.

Reviewed on Oct 20, 2026

Fleur Noire Hotel - 21 and Over

Uptown Design District

Save 100% on your flight

$462

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Los Angeles (LAX)

9.6/10 Exceptional! (1,003 reviews)

A very cutesy and quaint boutique hotel in the heart of downtown Palm Springs. The staff is very friendly and welcoming. The free amenities are thoughtful and appreciated. The hotel is close to many things. You can park your car and walk the area or bike it , using their complimentary bicycles. “Bri” was amazing. I’d come back again just to chat with her! I can’t wait to plan another getaway to this amazing property.

Reviewed on Oct 23, 2026

The Sofia Hotel

Downtown San Diego

Save 100% on your flight

$836

per person

Dec 30 - Jan 3

found 1 day ago

Roundtrip flight included

Dallas (DAL) to San Diego (SAN)

8.8/10 Excellent! (2,743 reviews)

Good trip. Be they helped me find my sunglasses

Reviewed on Oct 23, 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

$95 nightly

$108 total

Nov 22 - Nov 23

Total with taxes and fees

9.2/10 Wonderful! (1,303 reviews)

"Our experience was mostly very positive. The room was very clean and the bed was quite comfortable. My complaints are that the pool was too cold for an evening swim and the complimentary breakfast was not well maintained. We had to report to the desk that there were no eggs or biscuits. It took a ..."

Reviewed on Oct 19, 2026

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

Fully refundableReserve now, pay when you stay

$236 nightly

$269 total

Nov 23 - Nov 24

Total with taxes and fees

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$131 nightly

$149 total

Nov 23 - Nov 24

Total with taxes and fees

9.4/10 Exceptional! (2,731 reviews)

"Check in was easy and so polite and helpful. Hotel is immaculate. Breakfast was well maintained, lots to choose from, hot entrees were fresh appearing. So many choices, would have liked to try more, impossible to try everything! Very clean and attended to. Very quiet and will not hesitate to stay ..."

Reviewed on Oct 22, 2026

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.