Prospect Hill Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Prospect 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 $1,572, price is now CA $1,373 per person
CA $1,373
per person
Oct 12 - Oct 18
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.2/10 Wonderful! (208 reviews)
The location was perfect and everything we wanted for a girls weekend away!

Reviewed on Jul 28, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $3,163, price is now CA $2,661 per person
CA $2,661
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
No reviews

Where to stay in Prospect Hill

Find the best Prospect Hill areas and neighborhoods for the activities you enjoy most. Learn more about Prospect 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

Prospect Hill Hotel Deals

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
The price is CA $92 per night from Aug 5 to Aug 6
CA $92
CA $107 total
Aug 5 - Aug 6
includes taxes & fees
Motel 6 New Haven - Branford, CT
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Aug 13 to Aug 14
CA $225
CA $259 total
Aug 13 - Aug 14
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"It's an older hotel and very dated. The hallway and elevator carpets were worn out and stained. The rooms were clean, but dated. The food at the bar was not very good. I had the breakfast buffet it also left a lot to be desired."

Reviewed on Jul 30, 2026

Trumbull Marriott Shelton
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 13 to Aug 14
CA $154
CA $177 total
Aug 13 - Aug 14
includes taxes & fees
Best Western Executive Hotel Of New Haven - West Haven
See all 1,016 properties in Prospect 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
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Beach Vacations
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Family Vacations

Frequently asked questions

How much does a Prospect Hill vacation package cost?
From as low as CA $1,373. Yes, you read that right. Our Prospect Hill vacation packages are the quickest way to make your budget last longer. Combine your flights, hotels and rental car and discover this vibrant destination.
How do I get a cheap travel package to Prospect Hill?
Bundle your hotel and flight bookings, add extras such as a rental car or activities, and save with a Prospect Hill vacation package. You won't just walk away with superb discounts on your adventure — you'll have loads of choice too. When you book through Expedia, you'll have your pick of over 550 air carriers and 1,000,000 properties globally. Your dream vacation starts right here, right now!
Where should I stay in Prospect Hill?
A journey to Prospect Hill isn't complete without stopping by Yale University and Yale Bowl. Reserve a room within walking distance so you can easily access these impressive sights.
What are the top hotels in Prospect Hill?
The Blue Bird and The Haven - Feel At Home are among the most well-known properties in Prospect Hill. Why not have a look at the facilities and amenities at each and then make a decision?
How far in advance should I book my Prospect Hill vacation?
It depends on the airline, but you can generally browse through international fares on Expedia nearly a year in advance. While it's generally a good idea to book ahead of time, lucky customers will occasionally score a cheaper seat just weeks before departure dates.
What does an Expedia Prospect Hill travel package include?
Rental cars, flights and hotels, or any combination of them — it's your choice. Whether you're venturing to Prospect Hill with the family or adventuring with your friends, there's a package to fit every budget and style. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking a Prospect Hill travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and land fantastic discounts. Hotels aren't your only option, though. We have island villas, chalets in the middle of mountains and just about everything in between!
Can I choose my airline with a Prospect Hill Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply pick the airline you want and create your ideal Prospect Hill escape.
If I'm not able to travel, can I cancel my Prospect Hill vacation package?
Yes you can, and we'll help you every step of the way. You may be able to cancel and rebook your Prospect Hill vacation package at no cost within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company if your booking is older than that. If life gets in the way of your vacation, visit our Customer Service Portal for further information.

Stay near popular Prospect Hill attractions

Peabody Museum of Natural History

9.2/10 (30 reviews)
You can browse the exhibits at Peabody Museum of Natural History, a museum with a story of its own, during your travels to New Haven. Experience the area's art scene and museums.
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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.