Title: Chalk Hill Vacation Packages 2026 from $369 | Expedia.com

[Chalk Hill Travel Guide](https://expedia.com/Chalk-Hill.dx736342871657291776)[Hotels in Chalk Hill](https://expedia.com/Chalk-Hill-Hotels.d736342871657291776.Travel-Guide-Hotels)[Vacation Rentals in Chalk Hill](https://expedia.com/Chalk-Hill-Vacation-Rentals.d736342871657291776.Travel-Guide-VacationRentals)[Flights to Chalk Hill](https://expedia.com/Cheap-Flights-To-Chalk-Hill.d736342871657291776.Travel-Guide-Flights)[Car Rentals in Chalk Hill](https://expedia.com/Car-Rentals-In-Chalk-Hill.d736342871657291776.Car-Rental-Guide)

![](https://images.trvl-media.com/place/9542/b4ccdb92-b048-45af-b643-5a9cc297deeb.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chalk Hill Vacations from $369

## Book a Hotel + Flight or Car together to unlock savings

Photo by Rick Alvarez

- ##  
Plan, book, travel with confidence
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Better together  
Save up to $1,045 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
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Rest easy  
Plan, book, and manage your trip all in one place

### 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](https://www.expedia.com/Windsor.d9542.Destination-Travel-Guides) 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 Saguaro Palm Springs](https://images.trvl-media.com/lodging/1000000/30000/28000/27926/eb7aadaf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Saguaro Palm Springs

Sonora Sunrise

Save 100% on your flight

$369

per person

May 5 - May 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

8/10 Very Good! (1,027 reviews)

Loved the large spacious room! Beautiful pool and very colorful surroundings. We enjoyed our complimentary drink upon arrival. Will recommend this hotel.

Reviewed on Feb 23, 2026

![Malibu Country Inn](https://images.trvl-media.com/lodging/10000000/9780000/9778700/9778611/3a8c9456_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Malibu Country Inn

Central Malibu

$764

per person

May 5 - May 12

found 1 day ago

Roundtrip flight included

Denver (DEN) to Los Angeles (LAX)

7.8/10 Good! (1,000 reviews)

Exceptional staff and service! The rooms have a view of the beach and the mountains - what more could you ask for in gorgeous Malibu?

Reviewed on Feb 23, 2026

![SIRTAJ - Beverly Hills](https://images.trvl-media.com/lodging/7000000/6120000/6117200/6117111/868572f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SIRTAJ - Beverly Hills

South of Wilshire

Save 100% on your flight

$787

per person

May 16 - May 20

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Los Angeles (LAX)

8.4/10 Very Good! (1,001 reviews)

Excellent location, clean room, comfortable bed

Reviewed on Feb 15, 2026

![The Shoal La Jolla Beach](https://images.trvl-media.com/lodging/1000000/30000/26600/26508/ace1ba8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Shoal La Jolla Beach

Beach Barber Tract

$425

per person

May 6 - May 11

found 1 day ago

Roundtrip flight included

Denver (DEN) to San Diego (SAN)

8.8/10 Excellent! (1,001 reviews)

Front desk staff was wonderful & very accommodating. Accessible room was great except the bathroom. No hooks for towels or bench for clothing.

Reviewed on Feb 26, 2026

![Hollywood Inn Suites Hotel](https://images.trvl-media.com/lodging/28000000/27240000/27238100/27238098/918a7f8f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hollywood Inn Suites Hotel

Save 100% on your flight

$608

per person

May 6 - May 11

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Los Angeles (LAX)

8.2/10 Very Good! (1,622 reviews)

Stayed for three nights- aircon was very loud. Receptionist was not available for period of 20 or some min every night.

Reviewed on Feb 26, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chalk Hill

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-27/2026-04-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=NOT&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_736342871657291776)

### Discover the most popular places to visit in Chalk Hill

![You should flamin-go to Safari West and check out their #wildlife ](https://images.trvl-media.com/place/6208250/a162c7bd-d8e3-43ec-8ee2-36d0b6276ad3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Safari West

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 wineries. 

[](https://expedia.com/Safari-West-Santa-Rosa.d6208250.Vacation-Attraction)

#### 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 wineries. 

[](https://expedia.com/Chalk-Hill-Estate-Vineyard-Healdsburg.d6240787.Vacation-Attraction)

#### 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. 

[](https://expedia.com/Windsor-Oaks-Vineyards-Windsor.d6327443.Vacation-Attraction)

## Chalk Hill Hotel Deals

![Holiday Inn Express® Windsor Sonoma Wine Country by IHG](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/6e9c3a9c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane Windsor CA

Fully refundable

$103 nightly

$117 total

Mar 1 - Mar 2

Total with taxes and fees

9.2/10 Wonderful! (1,311 reviews)

Great room & breakfast.

Reviewed on Feb 16, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=1273394&PinnedHotelID=1273394&HadPinnedHotel=true&regionId=736342871657291776)

![The Inn at the Tides](https://images.trvl-media.com/lodging/1000000/20000/11800/11786/cb3cd68d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Inn at the Tides

800 Coast Hwy One Bodega Bay CA

$210 nightly

$240 total

Mar 5 - Mar 6

Total with taxes and fees

9.4/10 Exceptional! (1,605 reviews)

Beautiful location friendly staff nice breakfast Room was spacious and nicely furnished

Reviewed on Feb 26, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=11786&PinnedHotelID=11786&HadPinnedHotel=true&regionId=736342871657291776)

![Oxford Suites Sonoma County](https://images.trvl-media.com/lodging/16000000/15930000/15927800/15927732/03c264d1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA

Fully refundableReserve now, pay when you stay

$134 nightly

$153 total

Mar 1 - Mar 2

Total with taxes and fees

9.4/10 Exceptional! (2,478 reviews)

We love staying here.

Reviewed on Feb 26, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=15927732&PinnedHotelID=15927732&HadPinnedHotel=true&regionId=736342871657291776)

[See all 2,049 properties in Chalk Hill](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F28%2F2026&endDate=3%2F1%2F2026&regionId=736342871657291776)

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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- [Flights from San Diego (SAN) to Santa Rosa (STS) ](https://www.expedia.com/lp/flights/san/sts/san-diego-to-santa-rosa)
- [Flights from Orange County (SNA) to Santa Rosa (STS) ](https://www.expedia.com/lp/flights/sna/sts/orange-county-to-santa-rosa)

- [Chalk Hill Estate Vineyard ](https://www.expedia.com/Chalk-Hill-Estate-Vineyard-Healdsburg.d6240787.Vacation-Attraction)
- [Powell's Sweet Shoppe - Windsor ](https://www.expedia.com/Powells-Sweet-Shoppe-Windsor-Windsor.d553248621532640709.Vacation-Attraction)
- [Windsor Vacations ](https://www.expedia.com/Windsor.d9542.Destination-Travel-Guides)
- [Dom Whitney Tasting Lounge ](https://www.expedia.com/Dom-Whitney-Tasting-Lounge-Windsor.d553248621532640707.Vacation-Attraction)
- [Windsor Oaks Vineyards ](https://www.expedia.com/Windsor-Oaks-Vineyards-Windsor.d6327443.Vacation-Attraction)
- [Visit Windsor ](https://www.expedia.com/Windsor.dx9542)
- [Windsor Golf Club ](https://www.expedia.com/Windsor-Golf-Club-Windsor.d6327439.Vacation-Attraction)
- [Visit Mark West Springs ](https://www.expedia.com/Mark-West-Springs.dx553248635975868985)

- [Car rentals near Windsor ](https://www.expedia.com/Car-Rentals-In-Windsor.d9542.Car-Rental-Guide)
- [Suv Car Rentals in Windsor ](https://www.expedia.com/SUV-Car-Rentals-In-Windsor.d9542-tSUV.Car-Rental-Guide-Class)
- [Car rental Windsor Airport (STS) ](https://www.expedia.com/Car-Rentals-In-Sonoma-County.d6032115.Car-Rental-Guide)
- [Car rentals near Mark West Springs ](https://www.expedia.com/Car-Rentals-In-Mark-West-Springs.d553248635975868985.Car-Rental-Guide)

- [Windsor Vacation Rentals ](https://www.expedia.com/Windsor-Vacation-Rentals.d9542.Travel-Guide-VacationRentals)

- [Things to do in Windsor ](https://www.expedia.com/Things-To-Do-In-Windsor.d9542.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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