Prospect 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*

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    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

Your Prospect Vacation

When you organize a vacation package to Prospect, you can relax and enjoy your getaway knowing that all your travel plans have been made in advance. Discover the wonders of this vibrant city while staying in a neighborhood like Cheshire Historic District, which is good for history. Mount Southington Ski Area, Palace Theatre and Brass Mill Center are just some of the attractions worth visiting during your trip to Prospect. Whoever you're taking time off with and whether your budget is big or small, your ultimate Prospect vacation is just a few clicks away with Expedia.

Top Prospect Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was CA $652, price is now CA $585 per person
CA $585
per person
Aug 17 - Aug 20
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8/10 Very good! (1,664 reviews)
．

Reviewed on Jun 30, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,344, price is now CA $1,092 per person
CA $1,092
per person
Aug 17 - Aug 20
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was CA $846, price is now CA $700 per person
CA $700
per person
Aug 17 - Aug 20
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (2,194 reviews)
A basic property, but clean and well-maintained and convenient to New Haven.

Reviewed on Jun 30, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $929, price is now CA $797 per person
CA $797
per person
Aug 17 - Aug 20
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.

Reviewed on Jun 2, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $854, price is now CA $738 per person
CA $738
per person
Sep 7 - Sep 10
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
8.6/10 Excellent! (1,316 reviews)
Staff is pleasant and the room was spacious and comfortable.

Reviewed on Jun 24, 2026

Ready to book your vacation to Prospect?

 

Choose your dates

Prospect Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Jul 5 to Jul 6
CA $158
CA $182 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (2,209 reviews)
"A basic property, but clean and well-maintained and convenient to New Haven."

Reviewed on Jun 30, 2026

New Haven Hotel
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 $147 per night from Jul 5 to Jul 6
CA $147
CA $169 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very good! (1,691 reviews)
"．"

Reviewed on Jun 30, 2026

Best Western Executive Hotel Of New Haven - West Haven
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Jul 5 to Jul 6
CA $160
CA $184 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"I came to CT because my brother passed away. • Upon arrival, my room was nearly 80 degrees. When I requested another room, I was told that was not possible. Maintenance eventually arrived and determined that the thermostat had simply been left on “heat” instead of “cool.” This should have been identified ..."

Reviewed on Jun 30, 2026

Hilton Garden Inn Milford
See all 1,109 properties in Prospect
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 Prospect vacation package cost?
You'll find cheap prices from CA $585 on Expedia for your Prospect break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Prospect costs.
What are the cheapest months to go to Prospect?
January, February and March are the best times to look for cheap Prospect vacation packages. Choosing to travel in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Prospect?
Typically, a few days is great for a Prospect vacation. With a carefully crafted itinerary, you can go to all the top attractions including Holy Land USA, as well as discover some hidden treasures along the way.
How to find the best Prospect package deals?
Start your search for a Prospect package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Prospect package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Prospect adventure underway.
Is it cheaper to book a Prospect vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can customize your Prospect getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Prospect?
If you're planning a spur-of-the-moment Prospect getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Prospect?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Prospect.
  2. Budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Prospect.
  3. Decide how long to go away for: Now that you're more familiar with Prospect, you can figure out the perfect length of your break. Pull together a rough plan and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Prospect vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.