Photo by Joel Hayden
Holiday rentals near Chestnut Street
We found 2,193 holiday rentals — enter your dates for availability
Choose the perfect private holiday rental that's near Chestnut Street. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Chestnut Street
Showing deals for:3 Oct - 10 Oct
Image gallery for DREAM LUXURY Penthouse ★ Best View of San Francisco + FREE Valet
1010 out of 10 rating
Exceptional
(22 reviews)
DREAM LUXURY Penthouse ★ Best View of San Francisco + FREE Valet
San Francisco, CA
9% off
Price is NZ$9,599
NZ$9,599
NZ$1,371 per night
includes taxes & fees
Image gallery for CASABLANCA- Grand Edwardian View Home
1010 out of 10 rating
Exceptional
(16 reviews)
CASABLANCA- Grand Edwardian View Home
San Francisco, CA
15% off
Price is NZ$15,787
NZ$15,787
NZ$2,255 per night
includes taxes & fees
Image gallery for Mill Valley Home Near Muir Woods Redwoods Beaches San Francisco and Wine Country
1010 out of 10 rating
Exceptional
(7 reviews)
Mill Valley Home Near Muir Woods Redwoods Beaches San Francisco and Wine Country
Mill Valley, CA
8% off
Price is NZ$16,753
NZ$16,753
NZ$2,393 per night
includes taxes & fees
Image gallery for Floating condo 'B' on Sausalito's Richardson Bay
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Floating condo 'B' on Sausalito's Richardson Bay
Mill Valley, CA
8% off
Price is NZ$3,116
NZ$3,116
NZ$445 per night
includes taxes & fees
Image gallery for Spacious and Central 2BR Garden View Suite
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Spacious and Central 2BR Garden View Suite
San Francisco, CA
8% off
Price is NZ$2,113
NZ$2,113
NZ$302 per night
includes taxes & fees
Image gallery for Cottage Point for Extended Stay
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Cottage Point for Extended Stay
Richmond, CA
12% off
Price is NZ$1,798
NZ$1,798
NZ$257 per night
includes taxes & fees
Image gallery for 4 Bdrm Home- Great Outdoor Space-Perfect for Family Gatherings
1010 out of 10 rating
Exceptional
(43 reviews)
4 Bdrm Home- Great Outdoor Space-Perfect for Family Gatherings
Tiburon, CA
8% off
Price is NZ$9,591
NZ$9,591
NZ$1,370 per night
includes taxes & fees
Image gallery for Luxury, San Francisco Bay Area (Tiburon): 5000 sq. ft., 4 bed, 5 bath
1010 out of 10 rating
Exceptional
(45 reviews)
Luxury, San Francisco Bay Area (Tiburon): 5000 sq. ft., 4 bed, 5 bath
Tiburon, CA
22% off
Price is NZ$24,547
NZ$24,547
NZ$3,507 per night
includes taxes & fees
Image gallery for Modern 3BR Urban Oasis 🌿 Close to SF & Oakland Ballers 🏟️
9.09.0 out of 10 rating
Wonderful
(23 reviews)
Modern 3BR Urban Oasis 🌿 Close to SF & Oakland Ballers 🏟️
Emeryville, CA
8% off
Price is NZ$2,555
NZ$2,555
NZ$365 per night
includes taxes & fees
Image gallery for Point Oasis. Cozy Retreat. Walk to Keller Beach Park
1010 out of 10 rating
Exceptional
(6 reviews)
Point Oasis. Cozy Retreat. Walk to Keller Beach Park
Richmond, CA
8% off
Price is NZ$2,333
NZ$2,333
NZ$333 per night
includes taxes & fees
Image gallery for Mid-Century home with a beautiful view, deck, & rear fenced-in patio
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Mid-Century home with a beautiful view, deck, & rear fenced-in patio
Tiburon, CA
21% off
Price is NZ$10,974
NZ$10,974
NZ$1,568 per night
includes taxes & fees
Image gallery for A country retreat near San Francisco
1010 out of 10 rating
Exceptional
(289 reviews)
A country retreat near San Francisco
Mill Valley, CA
8% off
Price is NZ$4,252
NZ$4,252
NZ$607 per night
includes taxes & fees
Image gallery for @ Marbella Lane - Vibrant 5BR Home in Daly City
9.69.6 out of 10 rating
Exceptional
(5 reviews)
@ Marbella Lane - Vibrant 5BR Home in Daly City
Daly City, California
15% off
Price is NZ$6,347
NZ$6,347
NZ$907 per night
includes taxes & fees
Image gallery for Breathtaking Ocean Views from Every Room!
1010 out of 10 rating
Exceptional
(122 reviews)
Breathtaking Ocean Views from Every Room!
Sausalito, CA
7% off
Price is NZ$11,031
NZ$11,031
NZ$1,576 per night
includes taxes & fees
Image gallery for Luxury living minutes from the heart of SF! One block away from Bart station.
9.89.8 out of 10 rating
Exceptional
(41 reviews)
Luxury living minutes from the heart of SF! One block away from Bart station.
Daly City, CA
7% off
Price is NZ$15,879
NZ$15,879
NZ$2,268 per night
includes taxes & fees
Image gallery for Cozy Studio 2 Blocks from Downtown Mill Valley
9.49.4 out of 10 rating
Exceptional
(95 reviews)
Cozy Studio 2 Blocks from Downtown Mill Valley
Mill Valley, CA
8% off
Price is NZ$2,363
NZ$2,363
NZ$338 per night
includes taxes & fees
Image gallery for Brand New Equisite Modern Home Close To Hiking, Biking, San Fran, & Wine Country
1010 out of 10 rating
Exceptional
(23 reviews)
Brand New Equisite Modern Home Close To Hiking, Biking, San Fran, & Wine Country
Mill Valley, CA
8% off
Price is NZ$21,269
NZ$21,269
NZ$3,038 per night
includes taxes & fees
Image gallery for Recharge in Lush Gardens in the Heart of Bernal Heights
1010 out of 10 rating
Exceptional
(11 reviews)
Recharge in Lush Gardens in the Heart of Bernal Heights
San Francisco, CA
9% off
Price is NZ$2,308
NZ$2,308
NZ$330 per night
includes taxes & fees
Image gallery for ((::Newly Cozy 4 Beds and 2 baths Unit for you::))
1010 out of 10 rating
Exceptional
(8 reviews)
((::Newly Cozy 4 Beds and 2 baths Unit for you::))
Daly City, CA
8% off
Price is NZ$3,182
NZ$3,182
NZ$455 per night
includes taxes & fees
Image gallery for Century-Old San Francisco Yacht
9.29.2 out of 10 rating
Wonderful
(32 reviews)
Century-Old San Francisco Yacht
Sausalito, CA
8% off
Price is NZ$3,926
NZ$3,926
NZ$561 per night
includes taxes & fees
Image gallery for Live the Penthouse Dream – Luxe, Views & Vibes in Iconic North Beach
9.89.8 out of 10 rating
Exceptional
(79 reviews)
Live the Penthouse Dream – Luxe, Views & Vibes in Iconic North Beach
San Francisco, CA
30% off
Price is NZ$16,717
NZ$16,717
NZ$2,388 per night
includes taxes & fees
Image gallery for Hilltop Beauty with Breathtaking San Francisco View
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Hilltop Beauty with Breathtaking San Francisco View
Daly City, CA
9% off
Price is NZ$7,887
NZ$7,887
NZ$1,127 per night
includes taxes & fees
Image gallery for Lovely Mango House near SFO and Paradise Valley
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Lovely Mango House near SFO and Paradise Valley
South San Francisco, CA
11% off
Price is NZ$4,534
NZ$4,534
NZ$648 per night
includes taxes & fees
Image gallery for Mill Valley Tree House
9.69.6 out of 10 rating
Exceptional
(47 reviews)
Mill Valley Tree House
Mill Valley, CA
9% off
Price is NZ$4,799
NZ$4,799
NZ$686 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Chestnut Street
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Find the best place to stay - Chestnut Street
Showing deals for: 29 Sept - 2 Oct
Pacific Heights Victorian Bedroom & Bathroom
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
The current price is NZ$1,249
NZ$1,249
for 3 nights, 1 home
NZ$416 per night
includes taxes & fees
Experience a Tranquil Oasis at Marina Motel -San Francisco's Best Kept Secret!
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is NZ$1,792
NZ$1,792
for 3 nights, 1 home
NZ$597 per night
includes taxes & fees
A spectacular home with a three bridge view out the Golden Gate.
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
The current price is NZ$1,653
NZ$1,653
for 3 nights, 1 home
NZ$551 per night
includes taxes & fees
Vibrant Room Close to Wharf, Pier 39 & Tours | Perfect for Romantic Couple Stay
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is NZ$1,471
NZ$1,471
for 3 nights, 1 room
NZ$490 per night
includes taxes & fees
Vacation Day Is Always A Great Idea! Near Wax Museum at Fisherman’s Wharf
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
The current price is NZ$1,550
NZ$1,550
for 3 nights, 1 room
NZ$517 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value