Prospect Vacations from $226

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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.

The Latest Prospect vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $269, price is now $226 per person
$226
per person
Nov 14 - Nov 16
found 8 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,014 reviews)
Clean room, and friendly service - Good breakfast offered. Nice overall!

Reviewed on Sep 15, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was $278, price is now $232 per person
$232
per person
Nov 14 - Nov 16
found 8 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (432 reviews)
Went for a wedding and was stranded at the venue from the hotel! It wasn’t until I threatened them with a lawsuit and amazingly they found a way to get back to the venue but that was after I spent $40 on an Uber. The hotel was nice but extremely noisy with the highway right next door. If you build a hotel next to a highway you should sound proof your property!!

Reviewed on Sep 18, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $792, price is now $676 per person
$676
per person
Nov 25 - Nov 30
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.6/10 Excellent! (1,102 reviews)
Bulbs in the elevator need replacing

Reviewed on Sep 18, 2025

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $734, price is now $635 per person
$635
per person
Nov 25 - Nov 30
found 5 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
as always a class stay, clean and safe

Reviewed on Sep 17, 2025

Clarion Inn

Clarion Inn

3 out of 5
Price was $588, price is now $523 per person
$523
per person
Nov 11 - Nov 15
found 10 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
7.6/10 Good! (1,015 reviews)
It was an average place to stay, staff were friendly

Reviewed on Sep 16, 2025

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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
$148 nightly
The price is $170 total per night from Sep 28 to Sep 29
$170 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,766 reviews)
"Hotel was nice. Service was good"

Reviewed on Sep 15, 2025

New Haven Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $185 total per night from Sep 28 to Sep 29
$185 total
Sep 28 - Sep 29
Total with taxes and fees
8/10 Very Good! (1,008 reviews)
"The room was spacious and the bed was comfortable. I needed to be near St. Vincent’s Hospital and the hotel location was convenient. It’s a little run down here and there but it’s still clean and comfortable. I’d stay here again."

Reviewed on Sep 14, 2025

Trumbull Marriott Shelton
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$112 nightly
The price is $129 total per night from Sep 21 to Sep 22
$129 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (1,087 reviews)
"Rooms are clean, staff was very pleasant, breakfast was great"

Reviewed on Sep 13, 2025

Holiday Inn Express Southington by IHG
See all 977 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.

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Frequently asked questions

How much does a Prospect vacation package cost?
You can pick up a vacation package to this top destination from $226 on Expedia. But how much your vacation to Prospect costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Prospect?
If you're looking to book a cheap Prospect vacation package, consider traveling in December, January and February. You're likely to find lower rates on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Prospect?
Usually, a handful of days is enough to tick off the main sights during your Prospect vacation. However, if you want to have some time to rest or go on day trips, consider extending your itinerary.
How to find the best Prospect package deals?
Use Expedia's filter tool to help you find some tempting Prospect package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Prospect package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Prospect vacation as a package?
You can enjoy significant savings on your Prospect retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Prospect?
If you have your Prospect travel dates finalized, book early to score some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Prospect vacation packages?
Set off on your perfect escape to Prospect with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up bargains while they last.

Explore a world of travel with Expedia

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.