Title: Sleepy Hollow Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $813 Expedia.ca [Sleepy Hollow Travel Guide](https://expedia.ca/Orinda-Sleepy-Hollow.dx944528401323143168)[Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Hotels.d944528401323143168.Travel-Guide-Hotels)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d944528401323143168.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # 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 $1,096 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. ![Elm House Inn](https://images.trvl-media.com/lodging/7000000/6930000/6924700/6924685/20d86e6f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Elm House Inn Central Napa CA $813 per person May 28 - May 31 found 15 hours ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 9.6/10 Exceptional! (1,505 reviews) Cute place; I have stayed here twice and would come back. Nice coffee bar; lovely staff...who called me right away to let me know I had left something behind. Clean and comfortable! Reviewed on Mar 5, 2026 ![Sonesta Emeryville - San Francisco Bay Bridge](https://images.trvl-media.com/lodging/1000000/560000/551100/551060/472c4721_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sonesta Emeryville - San Francisco Bay Bridge CA $1,030 per person May 21 - May 25 just found Roundtrip flight included Toronto (YTO) to Oakland (OAK) 8.6/10 Excellent! (1,375 reviews) Very friendly helpful staff , room clean , other amenities out of order like the ice machine , our heater wasn’t working and i have a anemic child which i was Told the room would be changed never did Reviewed on Mar 8, 2026 ![Bel Abri Napa Valley Inn](https://images.trvl-media.com/lodging/1000000/920000/911000/910902/77d1ba5b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bel Abri Napa Valley Inn Central Napa CA $1,212 per person May 28 - May 31 found 15 hours ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 9.6/10 Exceptional! (1,000 reviews) I found my stay of 5 days very pleasant and the staff are wonderful. My room was spacious and clean. Reviewed on Mar 4, 2026 ![Vino Bello Resort](https://images.trvl-media.com/lodging/2000000/1510000/1509800/1509748/58aa71f4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Vino Bello Resort Soscol Gateway South CA $1,300 per person May 28 - May 31 found 15 hours ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 8.4/10 Very Good! (1,001 reviews) Very clean and spacious Reviewed on Jan 24, 2026 ## 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](https://expedia.ca/Orinda-Sleepy-Hollow.dx944528401323143168) ![Sunset over Rolling Grassy Hills and Mount Diablo in Northern California. Views from Briones Regional Park looking east. Contra Costa County, California, USA.](https://images.trvl-media.com/place/553248635976470528/9fb5bd11-bdfc-4d30-9d3b-906fbd91f11b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Northwood - Tara When in Northwood - Tara, you can plan a visit to Orinda Theater and Lafayette Reservoir, some noteworthy sights in the nearby area. [Find hotel + flight trips in Northwood - Tara](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Northwood%20-%20Tara&DestID=553248635976470528&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in Knickerbocker](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Knickerbocker&DestID=553248635976468563&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Glorietta While there might not be top attractions in Glorietta, you can explore the larger area and discover places like Orinda Theater and Lafayette Reservoir. [Find hotel + flight trips in Glorietta](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Glorietta&DestID=553248635976478184&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Mt. Diablo dawn panorama](https://images.trvl-media.com/place/553248635976473673/2eb7dac8-3538-42e6-b16a-e626cd7a8463.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wilder 2 out of top 10 points of interest in this area If you're spending some time in Wilder, Labyrinth and Labyrinth are top sights worth seeing. [Find hotel + flight trips in Wilder](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Wilder&DestID=553248635976473673&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Aerial Panorama of Oakland Hills in Northern California](https://images.trvl-media.com/place/553248635976478694/c92f3f93-8137-4aa8-853d-2c6b7b9c8ab1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lost Valley Though Lost Valley might not have many top sights, you can venture to the surrounding area to see attractions like Sibley Volcanic Regional Preserve and Orinda Theater. [Find hotel + flight trips in Lost Valley](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lost%20Valley&DestID=553248635976478694&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Sleepy Hollow Hotel Deals ![Holiday Inn Golden Gateway by IHG](https://images.trvl-media.com/lodging/1000000/20000/10600/10538/5971a3e7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Golden Gateway by IHG 1500 Van Ness Ave San Francisco CA Fully refundableReserve now, pay when you stay CA $183 CA $216 total Mar 29 - Mar 30 includes taxes & fees 9/10 Wonderful! (5,382 reviews) Air conditioning is great,Good size smart tv. GREAT WINDOW VIEW! Reviewed on Mar 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=10538&PinnedHotelID=10538&HadPinnedHotel=true®ionId=944528401323143168) ![Handlery Union Square Hotel](https://images.trvl-media.com/lodging/1000000/10000/6700/6666/4fd95a3a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Handlery Union Square Hotel 351 Geary St San Francisco CA Fully refundableReserve now, pay when you stay CA $203 CA $238 total Apr 1 - Apr 2 includes taxes & fees 8.8/10 Excellent! (2,922 reviews) Clean room Friendly staff Reviewed on Mar 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=6666&PinnedHotelID=6666&HadPinnedHotel=true®ionId=944528401323143168) ![Hotel Riu Plaza Fisherman's Wharf](https://images.trvl-media.com/lodging/1000000/30000/24700/24625/75f20517_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Fisherman's Wharf 2500 Mason St San Francisco CA Fully refundableReserve now, pay when you stay CA $200 CA $291 total Mar 18 - Mar 19 includes taxes & fees 9/10 Wonderful! (7,405 reviews) Clean, modern and comfortable room. Amazing breakfast buffet. Steps away from piers and Muni buses/trolley stops. Make sure you buy Muni day pass, no rental car is needed if you stay at Riu. Reviewed on Mar 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=18%2F03%2F2026&endDate=19%2F03%2F2026&selected=24625&PinnedHotelID=24625&HadPinnedHotel=true®ionId=944528401323143168) [See all 4,317 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F03%2F2026&endDate=11%2F03%2F2026®ionId=944528401323143168) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.