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 $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 The Hill

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Milford - New Haven

Red Roof Inn Milford - New Haven

2 out of 5
Price was CA $1,217, price is now CA $1,172 per person
CA $1,172
per person
Jun 27 - Jul 1
found 2 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
7/10 Good! (1,003 reviews)
The ice machine wasn't working. Neither one. Bur the staff was so nice!! It was clean and close to everything.. I will definitely stay there again.

Reviewed on Apr 12, 2026

Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $1,382, price is now CA $1,307 per person
CA $1,307
per person
Jun 27 - Jul 1
found 2 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
Clean and easy location to catch train to NYC

Reviewed on Apr 5, 2026

Springhill Suites Milford

Springhill Suites Milford

3 out of 5
Price was CA $1,567, price is now CA $1,527 per person
CA $1,527
per person
Jun 27 - Jul 1
found 2 hours ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.6/10 Excellent! (1,000 reviews)
Clean modern room. Spacious bathroom. Staff very friendly. Nice selection for breakfast.

Reviewed on Apr 8, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $3,812, price is now CA $2,360 per person
CA $2,360
per person
Jun 13 - Jun 17
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) 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
Downtown New Haven

Downtown New Haven

5 out of top 10 points of interest in this area
5/5(4 area reviews)

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! (68 reviews)
beat check in procedures! so clear, so informative. clean, spacious and lovely. parking was great.

Reviewed on Apr 12, 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! (31 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 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
Fully refundable
The price is CA $168 per night from May 3 to May 4
CA $168
CA $194 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (2,086 reviews)
Hotel is in a great location, perfect for walking around the area. Nearby parking is very convenient, but tight. Staff was friendlt, everything was clean, room was large and quality was fantastic. Would stay here again.

Reviewed on Apr 12, 2026

New Haven Hotel
See all 1,009 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 $1,172, 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.

Discover the most popular places to visit in The Hill

Yale university buildings in spring blue sky in New Haven, CT USA

Yale University

Enjoy the collegiate vibe around Yale University, a top college in New Haven. Stroll along the beaches or experience the area's art scene.

Yale University

Sterling Memorial Library at Yale University

After visiting Sterling Memorial Library at Yale University, make a plan to see the other sights and activities in New Haven. Experience the area's art scene and museums.

Sterling Memorial Library at Yale University
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.