Sleepy Hollow 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 Sleepy Hollow

Price found within the past 48 hours. Click for updated prices.
Stanford Court San Francisco

Stanford Court San Francisco

4 out of 5
Downtown San Francisco
Save 100% on your flight
Price was CA $1,045, price is now CA $647 per person
CA $647
per person
Jan 15 - Jan 18
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9/10 Wonderful! (1,793 reviews)
This is a great hotel for the price paid, in the best neighborhood possible in San Francisco. Decor is a bit dated and common areas could use some freshening, but it will remain my "go to" for a quick weekend or overnight in SF. Nice hotel gym. Great neighborhood for walking and exploring. Less expensive parking available off site but near by (check SpotHero). Complimentary coffee downstairs is great quality and there's always a nice morning buzz around the lobby in the AM hours. Staff is kind and considerate.

Reviewed on Nov 9, 2026

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Price was CA $1,353, price is now CA $889 per person
CA $889
per person
Jan 21 - Jan 26
found 15 hours ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9/10 Wonderful! (7,739 reviews)
The room we stayed in should not be a guest room. It should be a mechanical room. We did not get ANY sleep because of the sound of the hotel and neighbors wheeling and dumping trash cans and all employees working and talking loudly ALL NIGHT LONG every night! Horrible experience. Breakfast was good hotel was clean staff was nice the room should not have a guest stay in it ever.

Reviewed on Nov 9, 2026

Infinity Hotel San Francisco, Tapestry Collection by Hilton

Infinity Hotel San Francisco, Tapestry Collection by Hilton

4 out of 5
Marina District
Save 100% on your flight
Price was CA $4,741, price is now CA $3,290 per person
CA $3,290
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to San Francisco (SFO)
8.8/10 Excellent! (1,000 reviews)
The staff is amazing, Very helpful. Very friendly. Addressed all issues. Made my son's Halloween Wedding so easy. Thank you!

Reviewed on Nov 8, 2026

Stanyan Park Hotel

Stanyan Park Hotel

3 out of 5
Golden Gate
Price was CA $2,663, price is now CA $1,849 per person
CA $1,849
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
9.4/10 Exceptional! (1,005 reviews)
It was a historic and very well maintained property for its age. The property is well located with regard to the sf park and hospital

Reviewed on Nov 9, 2026

Hotel Nia, Autograph Collection

Hotel Nia, Autograph Collection

4.5 out of 5
Price was CA $4,535, price is now CA $3,168 per person
CA $3,168
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to San Francisco (SFO)
9/10 Wonderful! (617 reviews)

Sleepy Hollow Hotel Deals

Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
Fully refundable
The price is CA $168 per night from Nov 29 to Nov 30
CA $168
per night
Nov 29 - Nov 30
9/10 Wonderful! (6,487 reviews)
"Awesome experience"

Reviewed on Nov 9, 2026

Holiday Inn Golden Gateway by IHG
Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
2500 Mason St San Francisco CA
The price is CA $168 per night from Nov 29 to Nov 30
CA $168
per night
Nov 29 - Nov 30
9/10 Wonderful! (7,760 reviews)
"The room we stayed in should not be a guest room. It should be a mechanical room. We did not get ANY sleep because of the sound of the hotel and neighbors wheeling and dumping trash cans and all employees working and talking loudly ALL NIGHT LONG every night! Horrible experience. Breakfast was good ..."

Reviewed on Nov 9, 2026

Hotel Riu Plaza Fisherman's Wharf
Hilton San Francisco Union Square

Hilton San Francisco Union Square

4 out of 5
333 O'Farrell St. San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Nov 23 to Nov 24
CA $213
per night
Nov 23 - Nov 24
Hilton San Francisco Union Square
See all 2,949 properties in Sleepy Hollow
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

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
Starting from as low as CA $647, a vacation package is your gateway to inexpensive travel. Custom build your Sleepy Hollow getaway by selecting from our comprehensive range of hotels, flights and rental cars.
How do I get a cheap travel package to Sleepy Hollow?
Bundle your flights and hotels with Expedia to save big bucks on your next big adventure. With over 550 air carriers and 1,000,000 hotels globally, your Sleepy Hollow vacation package can be tailored exactly to suit your budget. With all that extra cash, why not include a few exciting tours and activities? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Sleepy Hollow is closer than you thought!
Where should I stay in Sleepy Hollow?
With loads to explore in Sleepy Hollow, we suggest you book a hotel close to its attractions. San Francisco Theological Seminary, American Legion Log Cabin and San Anselmo Memorial Park are some interesting ones to put on your to-do list.
What are the top hotels in Sleepy Hollow?
Whether you plan to stay for one night or longer in Sleepy Hollow, you'll get a great night's sleep at San Anselmo Retreat: Hiking, Biking And Relaxation. This place is the first choice for many travelers.
How far in advance should I book my Sleepy Hollow vacation?
While prices change frequently, we generally advise booking your spot as soon as possible. Most international fares become available on Expedia up to a year in advance. If you're booking late, you might still get lucky. Discount prices to Sleepy Hollow occasionally appear in the weeks prior to departure.
What does an Expedia Sleepy Hollow travel package include?
Much of that depends on you. You can select from a variety of Sleepy Hollow packages, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your Sleepy Hollow trip looks like, get set to save!
What should I know before booking a Sleepy Hollow travel package?
Booking all the parts of your trip together is one of the best ways to save. Combine your flights, car rentals and hotels into a tidy package. But it's not just hotels. Expedia features all types of properties, including vacation rentals like oceanfront condos and serviced residences. The list is almost endless!
Can I choose my airline with a Sleepy Hollow Expedia vacation package?
Yes, so take your pick! We have access to over 550 airlines all over the world, so you can customize your Sleepy Hollow trip according to your budget and travel needs.
If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?
Certainly, and we're here to help. You may be able to cancel or change your Sleepy Hollow vacation package at no cost if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, take a look at our Customer Service Portal for more information.

Things to do

Muir Woods and Sausalito 1/2 Day Tour

Muir Woods and Sausalito 1/2 Day Tour (Small Group)

CA $140
per adult
100% of travellers recommend
Muir Woods and Sausalito 1/2 Day Tour (Small Group)
Combo image of City sightseeing and Muir Woods National Monument entrance

Hop-on, Hop-off City Tour & Muir Woods Excursion

CA $198
per adult
92% of travellers recommend
Hop-on, Hop-off City Tour & Muir Woods Excursion
The Golden Hour at the Golden Gate

2hr. SUNSET Sailing Experience on San Francisco Bay

CA $210
per adult
2hr. SUNSET Sailing Experience on San Francisco Bay
See all activities in San Anselmo
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.