Sleepy Hollow Vacations from $307
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The Latest Sleepy Hollow Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hawthorn Suites by Wyndham Napa Valley
Shurtleff
Save 100% on your flight
Price was $468, price is now $307 per person
$307
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
8.8/10 Excellent! (1,004 reviews)
Room was clean but nothing fancy or special - average in amenities. Pool looked great but we didn’t use it Front desk and service staff very pleasant. Hot breakfast was decent. Only complaint is that it was very noisy at night with doors on the exterior - so not a great choice for a light sleeper like me. (Not to mention yelling outside by other guests.) It was certainly “good enough” and met our needs but for the money >$330 /nt I feel like we could’ve chosen a nicer quieter option.
Reviewed on Sep 29, 2025
Claremont Resort & Club
Claremont Hills
Save 100% on your flight
Price was $697, price is now $412 per person
$412
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
8.8/10 Excellent! (1,014 reviews)
A historical hotel, it was my first time being here, and enjoyed the status of it. They were doing renovations and construction, but were mindful of quiet hours. I appreciate that they are maintaining it to keep it as a nice resort. I would stay here again if there were more deals and value available.
Reviewed on Oct 1, 2025
Fairmont Sonoma Mission Inn & Spa
Save 100% on your flight
Price was $541, price is now $330 per person
$330
per person
Dec 15 - Dec 18
found 13 hours ago
Roundtrip flight included
Ontario (ONT) to Oakland (OAK)
8.6/10 Excellent! (1,000 reviews)
Liked the room; spacious and enjoyed the spa
Reviewed on Sep 24, 2025
Silverado Resort
Save 100% on your flight
Price was $602, price is now $392 per person
$392
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
8.8/10 Excellent! (1,051 reviews)
Outdoor dining/patio was very nice and beautiful views. Clean cottage, front desk staff was very courteous. Housecleaning was thorough and request for extra water was quick. Amenities in cottage missing were paper products like napkins/paper towels, no filtered water or ice. Other wise very nice and quite.
Reviewed on Sep 28, 2025
River Terrace Inn - A Noble House Hotel
Downtown Napa
Save 100% on your flight
Price was $751, price is now $495 per person
$495
per person
Dec 13 - Dec 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9/10 Wonderful! (1,005 reviews)
Everything was perfect!!
Reviewed on Sep 30, 2025
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Knickerbocker
1 out of top 10 points of interest in this area
Even though there aren't top sights in Knickerbocker, you can explore the larger area and take in top sights like Orinda Theater. Jump on the metro at Orinda Station to see more of the city.
Sleepy Hollow Hotel Deals
Holiday Inn Golden Gateway by IHG
1500 Van Ness Ave, San Francisco, CA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Nov 2 to Nov 3
$140 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (4,627 reviews)
"I enjoyed my stay"
Reviewed on Oct 1, 2025
Hilton San Francisco Financial District
750 Kearny St, San Francisco, CA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $124 total per night from Nov 2 to Nov 3
$124 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,825 reviews)
"Very good staff. Great location"
Reviewed on Sep 30, 2025
Hotel Riu Plaza Fisherman's Wharf
2500 Mason St, San Francisco, CA
Fully refundableReserve now, pay when you stay
$195 nightly
The price is $230 total per night from Oct 17 to Oct 18
$230 total
Oct 17 - Oct 18
Total with taxes and fees
8.8/10 Excellent! (6,908 reviews)
"Friendly staff and location"
Reviewed on Oct 2, 2025
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.
Discover the most popular places to visit in Sleepy Hollow
Briones Park
Explore the great outdoors at Briones Park, a lovely green space in Orinda. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Orinda Theater
You can get tickets for a performance at Orinda Theater during your trip to Orinda. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
California Shakespeare Theater
You can get tickets for a performance at California Shakespeare Theater during your stay in Orinda. Experience the entertainment choices and acclaimed theater scene in this vibrant area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.