Chalk Hill Vacations from $334
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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.
Hotel H-Wood
Hollywood
$334
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Denver (DEN) to Los Angeles (LAX)
6.2/10 (997 reviews)
The room had roaches, the toilet water dispenser was dripping water all night long and they charged $17 per vehicle. Not a good experience.
Reviewed on Aug 9, 2026
Claremont Resort & Club
Claremont Hills
$1,645
per person
Oct 16 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
9/10 Wonderful! (1,058 reviews)
Gorgeous historic hotel, top notch amenities. Stuff is very helpful and friendly. Restaurant is very good.
One thing to know - not all rooms are equally well located and appointed. Our room central AC was broken, and portable AC unit was very noisy. We asked to move to a different room, which was much better but had windows with frosted glass for privacy. Do inquire ahead of time to make sure you are booking a good room.
Reviewed on Aug 9, 2026
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.
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 wineries.
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 wineries.
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.
Chalk Hill Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane Windsor CA
Fully refundable
$122 nightly
$139 total
Aug 23 - Aug 24
Total with taxes and fees
Hampton Inn & Suites Windsor - Sonoma Wine Country
8937 Brooks Road South Windsor CA
Fully refundableReserve now, pay when you stay
$147 nightly
$168 total
Aug 16 - Aug 17
Total with taxes and fees
9.2/10 Wonderful! (1,014 reviews)
"Its usually good"
Reviewed on Aug 7, 2026
The Inn at the Tides
800 Coast Hwy One Bodega Bay CA
$276 nightly
$314 total
Aug 11 - Aug 12
Total with taxes and fees
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.
Find the Best Chalk Hill Vacation Packages
Chalk Hill Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
