Chalk Hill Vacations from $344
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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.
Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms
Hollywood
Price was $1,098, price is now $529 per person
$529
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)
9.2/10 Wonderful! (78 reviews)
Beds were good altough the bed covers were stained everything else was good.
Reviewed on Jul 31, 2025
Oceana Santa Monica, LXR Hotels & Resorts
Wilshire Montana
Price was $3,736, price is now $2,008 per person
$2,008
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
New York (NYC) to Los Angeles (LAX)
9.2/10 Wonderful! (477 reviews)
I recently stayed at this hotel and was truly impressed by the staff — everyone was attentive, kind, and went above and beyond to make my stay comfortable. Their service and attitude were definitely the highlight of my experience.
However, I was disappointed with the room maintenance. The toilet was not functioning properly, and the phone in the room didn’t work, which made it difficult to contact the front desk. These issues took away from what could have been a perfect stay.
Overall, the staff made a great impression, but the hotel needs to improve its maintenance and ensure that all facilities are in proper working order. With a few fixes, this place could easily become an excellent choice
Reviewed on Oct 13, 2025
SIRTAJ - Beverly Hills
South of Wilshire
Price was $736, price is now $396 per person
$396
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)
8.4/10 Very Good! (1,011 reviews)
Elevator is slow AF. Avoid if you are claustrophobic. Bed was uncomfortable, way too soft. I sank in it.
Reviewed on Nov 2, 2025
Glendale Hotel
Somerset
Price was $659, price is now $355 per person
$355
per person
Jan 9 - Jan 13
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)
8.4/10 Very Good! (2,813 reviews)
Beautifully maintained hotel, clean, great location, and easy booking.
Reviewed on Nov 3, 2025
Discover the most popular places to visit in Chalk Hill
Safari West
4.5/5(67 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
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.
Windsor Oaks Vineyards
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.
Chalk Hill Hotel Deals
Holiday Inn Express® Windsor Sonoma Wine Country by IHG
8865 Conde Lane, Windsor, CA
Fully refundable
$103 nightly
The price is $117 total per night from Nov 23 to Nov 24
$117 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (1,219 reviews)
Very convenient location. Good condition. Breakfast options were not always satisfying.
Reviewed on Nov 1, 2025
Holiday Inn Windsor Wine Country by IHG
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
$95 nightly
The price is $108 total per night from Nov 23 to Nov 24
$108 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
Very comfortable hotel with the best staff. The person who checked us in was so nice. The room was spotless and super comfortable
Reviewed on Oct 29, 2025
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel
3421 Cleveland Ave, Santa Rosa, CA
Fully refundable
$88 nightly
The price is $102 total per night from Nov 30 to Dec 1
$102 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (2,053 reviews)
Speedy check in with the most friendliest lady at the check of counter on the third shift she really is a gem
Reviewed on Nov 3, 2025
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.
