Name: Holiday Inn Windsor Wine Country by IHG
Price range: $108 total
Rating: 9

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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 Cole

Little Tuscany

Save 100% on your flight

$517

per person

Mar 12 - Mar 18

found 2 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)

8.4/10 Very Good! (307 reviews)

The room was pretty nice. Everything worked, including the sizeable that had Netflix and Prime. Shower was fully stocked with nice shampoos and toiletries. Only thing which was a little weird was there felt like, beyond the restaurant, there wasn’t anybody on staff at the hotel, but, to be fair, I stayed over Christmas, so it might be a little busier at other times. All in all, a great choice!

Reviewed on Dec 27, 2025

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Hollywood

$677

per person

Feb 11 - Feb 16

found 5 hours ago

Roundtrip flight included

New York (NYC) to Los Angeles (LAX)

9.2/10 Wonderful! (80 reviews)

This apartment was perfect for what we needed. It is central to many parts so you could walk if you wanted. We did rent a car so it was great that free parking for 2 spots was available. It was clean and had everything we needed for our short stay. I'd likely come and stay again when I am back in the area

Reviewed on Nov 10, 2025

Inn At Union Square

Union Square

$1,272

per person

Feb 5 - Feb 8

found 5 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to San Francisco (SFO)

9.2/10 Wonderful! (1,008 reviews)

Clean, quiet, and friendly staff

Reviewed on Jan 6, 2026

Limon Palm Springs

Warm Sands

$4,845

per person

Mar 17 - Mar 22

found 9 hours ago

Roundtrip flight included

Portland (PDX) to Los Angeles (LAX)

9/10 Wonderful! (53 reviews)

Such a cute and fun place to stay!

Reviewed on Sep 23, 2025

The Oasis

Save 100% on your flight

$1,070

per person

Mar 12 - Mar 18

found 2 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)

9/10 Wonderful! (1,001 reviews)

This was perfect for our family of 4, plenty of beds & bathrooms in the unit we rented. The pools were heated and clean. We would stay here again!

Reviewed on Dec 25, 2025

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Discover the most popular places to visit in Chalk Hill

These two rhinos were placed together in hopes of them mating but looks like they’re more interested in lazing around under the California sun 😎 #Wildlife

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

$99 nightly

$113 total

Feb 1 - Feb 2

Total with taxes and fees

9.2/10 Wonderful! (1,283 reviews)

Bare minimum with

Reviewed on Jan 4, 2026

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA

Fully refundableReserve now, pay when you stay

$118 nightly

$135 total

Jan 18 - Jan 19

Total with taxes and fees

9/10 Wonderful! (1,004 reviews)

Clean

Reviewed on Jan 2, 2026

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy Windsor CA

Fully refundable

$95 nightly

$108 total

Jan 11 - Jan 12

Total with taxes and fees

9/10 Wonderful! (1,032 reviews)

First time in the suite. Very happy.

Reviewed on Jan 3, 2026

See all 2,065 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.