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Chestnut Street Vacations

Pack those stellar shades. We have Chestnut Street vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Chestnut Street – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Chestnut Street vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Chestnut Street

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Chestnut Street vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Chestnut Street well.

Chestnut Street Flight + Hotel packages

Top Hotel Deals

See all 701 Hotels in Chestnut Street
Serrano Hotel

Serrano Hotel

405 Taylor St, San Francisco

The Serrano Hotel is steps away from Union Square, perfectly positioned in the Theater District of San Francisco, 2 blocks from the Powell Street cable car.

$129

$129
Hotel Whitcomb

Hotel Whitcomb

1231 Market St, San Francisco
3.5 out of 5.0

Located in the San Francisco theater district with a BART and MUNI station at its entrance, this downtown hotel is 6 blocks from Union Square and within a mile ...

$115

$115
Hotel Zoe San Francisco

Hotel Zoe San Francisco

425 North Point, San Francisco
4.5 out of 5.0

Hotel Zoe San Francisco is 2 blocks from Fisherman's Wharf, Pier 39, and the Alcatraz Island ferry.

$160

$160
Hotel Nikko San Francisco

Hotel Nikko San Francisco

222 Mason St, San Francisco
4.0 out of 5.0

The Asian-inspired Hotel Nikko San Francisco is located downtown, a 4-minute walk from Union Square and the designer shops of Westfield San Francisco Centre. ...

$157

$157
Travelodge San Francisco Airport-North

Travelodge San Francisco Airport-North

326 S Airport Blvd, South San Francisco
2.0 out of 5.0

This 200-room hotel is 2 miles north of San Francisco International Airport and 10 miles from downtown San Francisco.

$63

$63
The Park Central San Francisco

The Park Central San Francisco

50 3rd St, San Francisco
4.5 out of 5.0

Located in the heart of the South of Market district (SoMa), The Park Central San Francisco is across from Yerba Buena Gardens and close to the San Francisco ...

$127

$127
Hotel Union Square

Hotel Union Square

114 Powell St, San Francisco
4.0 out of 5.0

Situated on the cable car line in the downtown shopping district, the boutique hotel is 2 blocks from Union Square and 4 blocks from the Moscone Center and San ...

$122

$122
Hotel Zephyr

Hotel Zephyr

250 Beach Street, San Francisco
3.5 out of 5.0

This family-friendly San Francisco hotel is located on the waterfront, within a 5-minute walk of Wax Museum at Fisherman's Wharf, Pier 39, and Ripley's Believe ...

$161

$161
Hyatt Regency San Francisco

Hyatt Regency San Francisco

5 Embarcadero Center, San Francisco
4.0 out of 5.0

The 17-story Hyatt Regency is located on the Embarcadero waterfront, across from the Ferry Building Marketplace, close to the Embarcadero Center, Union Square, ...

$199

$199
Handlery Union Square Hotel

Handlery Union Square Hotel

351 Geary St, San Francisco
4.0 out of 5.0

A half-block from cable cars, this hotel is 2 blocks from Westfield San Francisco Shopping Centre; the Moscone Center and the San Francisco Museum of Modern ...

$139

$139

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.