Hillcrest Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Your Hillcrest Vacation
When you book a vacation package to Hillcrest, you can relax and enjoy your getaway knowing that all your travel arrangements are in order. Discover the many gems of this amazing city from your base in a neighborhood like Montrose, which is good for walking. You'll want to take in some sights during your trip to Hillcrest. Carve out some time for top attractions such as New York Country Club, Sunbridge Institute and St. Pauls Episcopal Church. Your dream Hillcrest vacation is a couple of clicks away. Search hotels, airfares and more on Expedia for a trip that's tailored to suit your travel style.
Top Hillcrest Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $1,763
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,902 reviews)
Lives the proximity of the location. Right in time square . The room size was a bit small but it was all good
Reviewed on Aug 23, 2026
Seven Beach Lane
CA $1,570
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (32 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.
Reviewed on Aug 21, 2026
Ready to book your vacation to Hillcrest?
Hillcrest Hotel Deals
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $179
CA $240 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very good! (1,261 reviews)
"Beautiful grounds. Rooms are dated. Limited amenities … pool with limited drinks and no food. Only restaurant is Michelin rated so excellent n pricey. Only breakfast is buffet … $29. No microwaves in room. Mile plus walk to anything."
Reviewed on Aug 23, 2026
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
CA $144
CA $176 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (2,859 reviews)
"every thing is ok in the property. I couldn’t find out anything wrong. if I will go back to New York staying the same hotel."
Reviewed on Aug 23, 2026
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
CA $245
CA $326 total
Aug 30 - Aug 31
includes taxes & fees
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.
What to do in Hillcrest
Guided Shared Group Forest Bathing Session in Serene Woodland Park
CA $77
per adult
Frequently asked questions
How much does a Hillcrest vacation package cost?
You can pick up a vacation package to this destination from CA $1,113 on Expedia. However, how much your vacation to Hillcrest costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Hillcrest?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Hillcrest vacation packages and you could get some great off-season deals.
How many days is enough for Hillcrest?
The ideal duration of your Hillcrest vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to go to all the major attractions and discover some hidden spots along the way.
How to find the best Hillcrest package deals?
Bagging a cheap Hillcrest package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable Hillcrest package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Hillcrest vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights separately. Better still, you can customize your Hillcrest trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Hillcrest?
Secure fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Hillcrest getaway.
How to plan a trip to Hillcrest?
- Pick your dates: What you'd like to do in Hillcrest and your favourite season can help you decide when to travel.
- Plan your budget wisely: On top of the price of your stay, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Hillcrest.
- Work out your trip length: Think about how long you'd like to spend discovering Hillcrest. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Combine your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the right Hillcrest vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
