Prospect Vacation Packages

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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.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was CA $1,033, price is now CA $947 per person
CA $947
per person
Jan 1 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.4/10 Very good! (895 reviews)
This inn has a lot of potential but unfortunately it was extremely dirty. The room smelled so bad that I could hardly breathe and there was a thick layer of dirt on the walls and baseboards. The bed made a loud creaking noise with any subtle move. I felt so dirty when I left there. We were supposed to leave at 10am and I made my husband get up and drive home at 6am because I couldn't stand to be there any longer. I should have done more research about the property before I stayed but I used to live in Cheshire and it is such a nice town that it really just didn't cross my mind that a place so dirty would be there. The lady who checked me in was very nice and friendly but besides that I have nothing positive to say about my stay.

Reviewed on Nov 13, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,068, price is now CA $1,588 per person
CA $1,588
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
No reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was CA $1,276, price is now CA $1,095 per person
CA $1,095
per person
Jan 1 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.8/10 Excellent! (1,000 reviews)

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was CA $1,256, price is now CA $1,101 per person
CA $1,101
per person
Jan 1 - Jan 4
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,368, price is now CA $1,263 per person
CA $1,263
per person
Dec 24 - Dec 26
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) 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

Ready to book your vacation to Prospect?

 

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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 $174 per night from Nov 27 to Nov 28
CA $174
CA $200 total
Nov 27 - Nov 28
includes taxes & fees
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 $144 per night from Dec 1 to Dec 2
CA $144
CA $166 total
Dec 1 - Dec 2
includes taxes & fees
Best Western Executive Hotel Of New Haven - West Haven
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Dec 10 to Dec 11
CA $157
CA $181 total
Dec 10 - Dec 11
includes taxes & fees
Hyatt Place Milford / New Haven
See all 1,102 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 $947 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.

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