Title: Chalk Hill Vacation Packages 2026 from $215 | 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 $215

## 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 LEEF Hotel](https://images.trvl-media.com/lodging/114000000/113840000/113831500/113831485/55239c28_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The LEEF Hotel

Citrus Grove

Save 100% on your flight

$215

per person

May 15 - May 17

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Los Angeles (LAX)

8.4/10 Very Good! (326 reviews)

Very simple and great place for a short stay

Reviewed on Feb 23, 2026

![The Sofia Hotel](https://images.trvl-media.com/lodging/2000000/1580000/1573900/1573807/ba6cea84_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Sofia Hotel

Downtown San Diego

Save 100% on your flight

$640

per person

May 18 - May 23

found 1 day ago

Roundtrip flight included

Chicago (CHI) to San Diego (SAN)

8.4/10 Very Good! (1,627 reviews)

The staff was good. However, the room had three separate hairs. One black hair in the sink, one black hair in the shower, and one grey hair on the bed. Also, there was a candy wrapper on the floor underneath the vanity. They need to do a much better job of cleaning. That’s the stuff that I found and I’m sure there was more. Also, one of the lights in the bedroom kept turning on automatically, and I had to call management at three in the morning to come and remove the lightbulb because I couldn’t do it myself. Overall, not too good of an experience at this hotel.

Reviewed on Feb 24, 2026

![Royal Sun Palm Springs](https://images.trvl-media.com/lodging/2000000/1050000/1044200/1044191/2afd6e76_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Royal Sun Palm Springs

Save 100% on your flight

$356

per person

Apr 27 - May 1

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Los Angeles (LAX)

8.4/10 Very Good! (236 reviews)

Staff was courteous, room was clean. Paying the $40 amenity fee per room upon arrival was unexpected. The water pressure in the shower was a trickle, barely any water pressure at all (hard to get shampoo out). Toilet ran all night long. The hotel ran out of self parking spots so we had to park across the street in a dirt lot which wasn’t ideal. The restaurant was great!

Reviewed on Feb 2, 2026

![Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms](https://images.trvl-media.com/lodging/99000000/98270000/98260500/98260496/ebc393eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Hollywood

$945

per person

Apr 26 - May 2

found 1 day ago

Roundtrip flight included

New York (NYC) to Los Angeles (LAX)

9.2/10 Wonderful! (80 reviews)

We loved our stay here! Having an apartment was home away from home. Quiet neighborhood, close to everything. Comfy beds are hard to find and i was very pleased. Host was quick to respond.

Reviewed on Jan 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

$687

per person

Apr 9 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Los Angeles (LAX)

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

Excellent location, clean room, comfortable bed

Reviewed on Feb 15, 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/2026-03-24/2026-03-31/?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)

#### 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 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)

## 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! (1,310 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! (1,608 reviews)

Beautiful clean room with an ocean view. Complimentary chilled bottle of wind to local winery. Staff was very courteous and helpful. I hope to be able to return again later this year.

Reviewed on Feb 23, 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

$130 nightly

$148 total

Feb 26 - Feb 27

Total with taxes and fees

9.4/10 Exceptional! (2,482 reviews)

The room was clean. Fresh towels were brought and trash removed. The hotel was very nice and Staff was courteous and helpful. We used the hot tub and sauna and both worked perfectly and were clean.

Reviewed on Feb 23, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%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%2F25%2F2026&endDate=2%2F26%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 to Windsor ](https://www.expedia.com/Cheap-Flights-To-Windsor.d9542.Travel-Guide-Flights)
- [Flights from Windsor ](https://www.expedia.com/lp/flights/9542/flights-from-windsor)
- [Phoenix to Windsor ](https://www.expedia.com/lp/flights/178298/9542/phoenix-to-windsor)
- [Flights from Los Angeles (LAX) to Santa Rosa (STS) ](https://www.expedia.com/lp/flights/lax/sts/los-angeles-to-santa-rosa)
- [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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