Chalk Hill Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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 is one of the most popular cities to explore during a trip to Chalk Hill. Whether you're travelling for a couple of days or a couple of weeks, Expedia are here to help you customize your next Chalk Hill vacation.

Top Chalk Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.6/10 Excellent! (115 reviews)
Loved it!! Would definitely recommend this place.

Reviewed on Aug. 10, 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Los Angeles (LAX)
8.4/10 Very Good! (1,002 reviews)
Clean hotel with great service. The only downsides to this property is that the $150 deposit wasn’t disclosed until after I already booked and prepaid for the room & the parking is $40 a night (in a garage that’s across the street). Other than that, this is a great place to spend a night or two.

Reviewed on Aug. 9, 2025

Four Seasons Los Angeles at Beverly Hills

Four Seasons Los Angeles at Beverly Hills

5 out of 5
Beverly Grove
per person
Oct 6 - Oct 11
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
9.6/10 Exceptional! (762 reviews)
Excellent property and service. 5-10 minutes away from a good selection of restaurants.

Reviewed on Aug. 6, 2025

LA Crystal Hotel - Los Angeles Area

LA Crystal Hotel - Los Angeles Area

3 out of 5
Rancho Dominguez
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8/10 Very Good! (1,001 reviews)
Everything was almost perfect. Flexible with check in, rooms were clean, amenities were good. Only that bathroom door knob was broken.

Reviewed on Jul. 26, 2025

Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
West Athens
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.2/10 Very Good! (1,510 reviews)
Hotel itself was very nice, surrounding area was not

Reviewed on Aug. 9, 2025

Ready to book your vacation to Chalk Hill?

 

Choose your dates

Chalk Hill Hotel Deals

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

3 out of 5
8755 Old Redwood Hwy, Windsor, CA
Fully refundable
The price is CA $142 per night from Aug 25 to Aug 26
CA $142
CA $162 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Awesome !"

Reviewed on Aug. 6, 2025

Holiday Inn Windsor Wine Country by IHG
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

2.5 out of 5
8865 Conde Lane, Windsor, CA
Fully refundable
The price is CA $168 per night from Sep 4 to Sep 5
CA $168
CA $191 total
Sep 4 - Sep 5
includes taxes & fees
9.2/10 Wonderful! (1,105 reviews)
"Comfy bed"

Reviewed on Aug. 8, 2025

Holiday Inn Express® Windsor Sonoma Wine Country by IHG
Hampton Inn & Suites Windsor - Sonoma Wine Country

Hampton Inn & Suites Windsor - Sonoma Wine Country

2.5 out of 5
8937 Brooks Road South, Windsor, CA
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Aug 20 to Aug 21
CA $180
CA $206 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Very clean! Extremely friendly staff."

Reviewed on Jul. 30, 2025

Hampton Inn & Suites Windsor - Sonoma Wine Country
See all 2,060 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Chalk Hill

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 wineries.

Windsor Oaks Vineyards

Frequently asked questions

How much does a Chalk Hill vacation package cost?
From as little as CA $640, you can build your own Chalk Hill vacation package. Simply combine flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Chalk Hill?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we've got them all covered. Select the combination that suits you and watch your savings grow. We know a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotel options globally, which lets you customize your Chalk Hill vacation.
What are the top hotels in Chalk Hill?
Take a look at Inn At Rohnert Park and Oxford Suites Sonoma County. They're top picks for many travelers headed to Windsor. If Larkfield-Wikiup features on your itinerary, Flamingo Resort & Spa and Hotel La Rose are both great options.
How far in advance should I book my Chalk Hill vacation?
It can be difficult to know exactly when is the perfect time to book your vacation to Chalk Hill. But generally the earlier you book, the lower the prices. In some cases, you can book your flights and hotels up to a year prior to your departure date. If you're hoping for a last-minute getaway, no need to panic! There are incredible deals popping up on Expedia all the time.
What does an Expedia Chalk Hill travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to build your perfect Chalk Hill package. Once you've made your booking, you can add on the fun things like activities and tours. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a Chalk Hill travel package?
Discover deals to match your budget with an Expedia package. Hotels, flights, rental cars — we've got all of them. You'll save big bucks just for combining your bookings. Whether you're taking off on an adventure in the snow or drinking cocktails on a beach, your dream getaway is just clicks away.
Can I choose my airline with a Chalk Hill Expedia vacation package?
You sure can. We offer more than 550 airline partners across the globe, so go with the carrier that matches your travel preferences.
If I'm not able to travel, can I cancel my Chalk Hill vacation package?
You sure can, and we'll help you every step of the way. You may be able to cancel and rebook your Chalk Hill vacation package for free within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company for older bookings. If life gets in the way of your vacation, take a look at our Customer Service Portal for more information.

Other vacations you might like

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