The Hill 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 The Hill

Price found within the past 48 hours. Click for updated prices.
The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was CA $704, price is now CA $669 per person
CA $669
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.2/10 Wonderful! (227 reviews)

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was CA $4,046, price is now CA $3,356 per person
CA $3,356
per person
Dec 19 - Dec 26
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
No reviews

Where to stay in The Hill

Find the best The Hill areas and neighborhoods for the activities you enjoy most. Learn more about The Hill
A lighthouse on a rocky shoreline with people near the water.

Downtown New Haven

4 out of top 10 points of interest in this area

In the heart of New Haven, this residential downtown area boasts a variety of restaurants, cafes, theaters, and stores. Explore the arts at Chapel Street Historic District, Broadway area, and Ninth Square district, or visit the Shops at Yale.

Find hotels in Downtown New Haven

The Hill Hotel Deals

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
240 Congress Avenue New Haven CT
9.6/10 Exceptional! (93 reviews)
"We stayed for a week and had a great trip, apartment was clean and cozy and the bathroom was very big. When we come back we will consider staying here again"

Reviewed on Oct 26, 2026

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Luxury Furnished Apartments by Hyatus Downtown at Yale
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
9 Tower Ln New Haven CT
9.2/10 Wonderful! (36 reviews)
"Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again."

Reviewed on Oct 25, 2026

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Hyatus Luxury Residences City Crossing
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
The price is CA $170 per night from Nov 25 to Nov 26
CA $170
CA $195 total
Nov 25 - Nov 26
includes taxes & fees
New Haven Hotel
See all 1,026 properties in The Hill
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 The Hill vacation package cost?
The cheapest The Hill vacation package is CA $669, so your dream escape can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to create a package that suits you.
How do I get a cheap travel package to The Hill?
Bundle your hotel and flight bookings, add extras such as activities, and save with a The Hill vacation package. You won't just pick up amazing discounts on your adventure — you'll have lots of choice at your fingertips too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 hotels worldwide. Your unforgettable vacation starts right here, right now!
Where should I stay in The Hill?
Travelers come from every corner of the globe to experience Yale University and Yale Bowl in The Hill. Book a hotel near these popular attractions and visit them whenever you want.
What are the top hotels in The Hill?
Book a room at Luxury Furnished Apartments By Hyatus At Amistad Park. It's one of the neighborhood's most popular hotels. Another well-known option in The Hill is Luxury Furnished Apartments By Hyatus Downtown At Yale.
How far in advance should I book my The Hill vacation?
Browse Expedia to compare international fares as soon as you know your travel dates. In many cases, you can purchase a ticket up to a year prior to departure. If you can't find your preferred carrier, or you have to book last minute, don't worry. The lowest prices to The Hill sometimes emerge within weeks of the date of departure.
What does an Expedia The Hill travel package include?
Expedia has all you need to plan your The Hill getaway, but how you structure your package is your choice. Choose from a combination of flights, rental cars and hotels. Chasing some activities or tours to keep you entertained? Once you've made your booking, you can add them on too. No matter your budget or style, there's a deal to suit your needs.
What should I know before booking a The Hill travel package?
Bundling your bookings into a The Hill vacation package is the most convenient way to organize your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a The Hill Expedia vacation package?
Yes, so take your pick! We have access to over 550 airlines across the globe, so you can tailor your The Hill adventure according to your budget and travel needs.
If I'm not able to travel, can I cancel my The Hill vacation package?
It is possible to cancel your The Hill booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

Things to do

New Haven's Ghost Walk

New Haven's Ghost Walk

CA $37
per adult
New Haven's Ghost Walk
See all activities in New Haven
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.