Overlook Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Overlook

Price found within the past 48 hours. Click for updated prices.
Sheraton Sonoma Wine Country Petaluma

Sheraton Sonoma Wine Country Petaluma

3.5 out of 5
Price was CA $1,467, price is now CA $1,070 per person
CA $1,070
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.2/10 Very Good! (1,000 reviews)
This property is ideal for people traveling with dogs as there is a fantastic dog park/dog walk adjacent to the property. Very safe, clean and convenient.

Reviewed on Apr 30, 2026

Hotel Yountville

Hotel Yountville

4 out of 5
Price was CA $2,492, price is now CA $1,736 per person
CA $1,736
per person
Jul 28 - Aug 1
found 8 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (1,002 reviews)
Wonderful stay all around.

Reviewed on May 1, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Price was CA $3,890, price is now CA $2,829 per person
CA $2,829
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9.6/10 Exceptional! (716 reviews)
The room was very comfortable & what I expected from the pictures. The best treat was the spa experience. We enjoyed the workout facility, massages, the sauna, magnesium outdoor hot tub, adult pool etc. Food was good. We enjoyed biking from hotel into town. Lovina had amazing brunch. Fan of the Napa/Calistoga Valley area! We’ll be back.

Reviewed on May 7, 2026

Inn At Sonoma - A Four Sisters Inn

Inn At Sonoma - A Four Sisters Inn

3.5 out of 5
Price was CA $3,685, price is now CA $2,706 per person
CA $2,706
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
9/10 Wonderful! (1,003 reviews)
The breakfast was great and the staff excellent!

Reviewed on Apr 23, 2026

Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
Price was CA $2,286, price is now CA $1,688 per person
CA $1,688
per person
Jul 1 - Jul 5
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
8.4/10 Very Good! (1,000 reviews)
not exposed or told of spa. room = no utensils. surprised by sales pitch upon checking in.

Reviewed on Mar 22, 2026

Where to stay in Overlook

Find the best Overlook areas and neighborhoods for the activities you enjoy most. Learn more about Overlook
Dinosaur Hill Park at Sunset

Downtown Walnut Creek

3 out of top 10 points of interest in this area

While you're in Downtown Walnut Creek, take in top sights like Lesher Center for the Arts and jump on the metro at Walnut Creek Station to see more of the city.

Find hotels in Downtown Walnut Creek

Overlook Hotel Deals

DoubleTree by Hilton Hotel Berkeley Marina

DoubleTree by Hilton Hotel Berkeley Marina

4 out of 5
200 Marina Blvd Berkeley CA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from May 24 to May 25
CA $187
CA $215 total
May 24 - May 25
includes taxes & fees
8.2/10 Very Good! (4,594 reviews)
It was such a nice stay. It was super clean and Quiet. The staff were super sweet and helpful. I would highly recommend this location and will definitely stay here again. The location was close to good food and activities and they let me check in early when my seminar time changed.

Reviewed on May 10, 2026

DoubleTree by Hilton Hotel Berkeley Marina
The Marina Inn on San Francisco Bay

The Marina Inn on San Francisco Bay

3.5 out of 5
68 Monarch Bay Dr San Leandro CA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from May 21 to May 22
CA $143
CA $163 total
May 21 - May 22
includes taxes & fees
8.6/10 Excellent! (2,444 reviews)
Amazing people working there .

Reviewed on May 9, 2026

The Marina Inn on San Francisco Bay
Hyatt Regency San Francisco

Hyatt Regency San Francisco

4 out of 5
5 Embarcadero Center San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $300 per night from May 25 to May 26
CA $300
CA $415 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,225 reviews)
They give you a $20 credit for the restaurant, when you check out they don’t apply it.

Reviewed on May 9, 2026

Hyatt Regency San Francisco
See all 2,081 properties in Overlook
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
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Frequently asked questions

How much does an Overlook vacation package cost?
From just CA $1,070. Yes, you read that right. Our Overlook vacation packages are an awesome way to stretch your budget further. Combine your favorite hotels, flights and car rentals and get to know this destination your way.
How do I get a cheap travel package to Overlook?
One word: bundle. Flights, hotels and rental cars — combine whatever you need into an Overlook vacation package and save. Score even more discounts when you include extras such as day tours to your booking. But that's not the only good part. You have the freedom to customize your vacation your own way. We offer over 550 partner airlines and 1,000,000 hotel options worldwide, so that everyone has an opportunity to travel and live out those vacation dreams.
Where should I stay in Overlook?
With popular attractions like Broadway Plaza and John Muir Health in this neighborhood, try to find a hotel situated near either of them. Lesher Center for the Arts is another Overlook sight that draws the crowds.
What are the top hotels in Overlook?
Top Of The Hill Private Estate is one of Overlook's top properties. Book a room here and you can rest easy knowing you're in excellent hands.
How far in advance should I book my Overlook vacation?
Search Expedia to compare international airfares as soon as you've got your travel dates. In many cases, you can purchase a seat up to 12 months prior to departure. If you don't see your preferred air carrier, or you've left things to the last minute, don't despair. Cheap fares to Overlook sometimes occur a few weeks before departure.
What does an Expedia Overlook travel package include?
Rental cars, flights and hotels — we have them well covered. With Expedia, you can create your Overlook travel package just the way you want. All you have to do is determine what you need. Once you've made your booking, you can add extras like activities and experiences. The more you bundle, the more you save!
What should I know before booking an Overlook travel package?
Bundling your bookings into an Overlook vacation package is the most convenient way to organize your trip. Not only that, you'll get great discounts when you combine your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with an Overlook Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just choose the carrier you want and create your ideal Overlook vacation.
If I'm not able to travel, can I cancel my Overlook vacation package?
You can. We get that even the best-laid plans can fail, so we're here to help if you need to make changes to your Overlook vacation package. It may be possible to amend or cancel your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.