Chess Vacation Packages

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Top Holiday Package Deals in Chess

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

The Lodge at Tiburon

CA $1,065

per person

Sep 15 - Sep 18

found 11 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to San Francisco (SFO)

8.6/10 Excellent! (1,013 reviews)

I have stated here many times . Ever since new ownership came in it is rather obvious that things have gone downhill substantially. In my 60+ years of staying in hotels I have never experienced one where there is no daily room service. Traveling with children and coming home at 8.30 pm only to find a messy room with no fresh towels etc is simply unacceptable . If they choose to cut corners it should be clearly indicated at time of booking which it is NOT. Too bad as they took a property with lots of potential and downgraded it substantially turning it into a “cheap”motel instead even though the rates are clearly not commensurate with a such an establishment

Reviewed on Aug 9, 2026

Claremont Resort & Club

Claremont Hills

CA $1,505

per person

Sep 25 - Sep 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

9/10 Wonderful! (1,064 reviews)

Lovely visit to the Claremont. Quick check and friendly staff. Limewood restaurant was great for breakfast. The pool area was fantastic!

Reviewed on Aug 11, 2026

The Huntington Hotel

Downtown San Francisco

CA $3,580

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to San Francisco (SFO)

9.4/10 Exceptional! (28 reviews)

Dinah's Garden Hotel

CA $1,470

per person

Sep 15 - Sep 18

found 11 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to San Francisco (SFO)

9.6/10 Exceptional! (1,006 reviews)

Cavallo Point

CA $2,298

per person

Oct 9 - Oct 13

found 23 hours ago

Roundtrip flight included

Vancouver (YVR) to San Francisco (SFO)

9.2/10 Wonderful! (1,000 reviews)

This hotel is very nice and great location. Only 10-15 minute bike ride to Sausalito and 10 minute bike ride to the Golden Gate Bridge. Really great solitude just on the edges of San Francisco. Suggest staying in the newer modern rooms and upgrade to a suite.

Reviewed on Aug 11, 2026

Where to stay in Chess

Find the best Chess areas and neighborhoods for the activities you enjoy most. Learn more about Chess

A marina with various boats docked, including a yellow and white boat named 'Golden Gate'.

Fisherman's Wharf

1 out of top 10 points of interest in this area

Discover Pier 39, Ghirardelli Square, and the San Francisco Maritime National Historical Park in this bustling tourist hotspot. Savor seafood at family-owned restaurants and explore the sea lion colony, while enjoying convenient cable car access.

A cityscape with tall buildings, palm trees, and red double-decker buses.

Union Square

Major tourist destination in downtown San Francisco, Union Square boasts shopping, hotels, and theaters. Explore department stores, boutiques, and galleries, or catch a performance at various theaters. Enjoy the Dewey Monument and stunning views from nearby hotels. Easily accessible via cable car lines, buses, and subway systems.

A trolley on a street with buildings and a clock tower.

Downtown San Francisco

3 out of top 10 points of interest in this area

Serving as San Francisco's central business district, this area boasts Northern California's two tallest buildings, the Salesforce Tower and Transamerica Pyramid. Explore shopping malls like the Embarcadero Center and enjoy parks such as Sue Biermann Park, all easily accessible via Muni bus and rail lines.

A cityscape with modern skyscrapers, a central park with pathways, and a few people walking.

South of Market

From baseball games to top-notch art exhibits, find endless entertainment in one of San Francisco’s fastest-growing neighborhoods.

A cityscape with a prominent skyscraper, a bridge, and a mix of modern and historic buildings.

Nob Hill

Luxury hotels, historic mansions, and Michelin-starred restaurants abound in this upscale area. Explore Union Square shopping district, Grace Cathedral, and the SF Masonic Auditorium for a taste of culture and history.

Chess Hotel Deals

Holiday Inn Golden Gateway by IHG

1500 Van Ness Ave San Francisco CA

Fully refundable

CA $212

CA $249 total

Sep 7 - Sep 8

includes taxes & fees

9/10 Wonderful! (6,138 reviews)

"great room! super nice view of the city!!"

Reviewed on Aug 13, 2026

Hotel Riu Plaza Fisherman's Wharf

2500 Mason St San Francisco CA

Fully refundableReserve now, pay when you stay

CA $183

CA $273 total

Aug 31 - Sep 1

includes taxes & fees

Club Quarters Hotel in San Francisco

424 Clay St San Francisco CA

Fully refundableReserve now, pay when you stay

CA $183

CA $215 total

Aug 23 - Aug 24

includes taxes & fees

See all 4,163 properties in Chess

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.