Prospect Vacations from $383

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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.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $492, price is now $383 per person
$383
per person
Nov 25 - Nov 29
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (575 reviews)
Didn't get a chance to enjoy the breakfast or pool as intended, however customer service and cleanliness was outstanding! Plus they gave a small welcome bag with some water and little treats/snacks! Parking was easy, and location even though was by highway, was relatively quiet!

Reviewed on Oct 11, 2025

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $1,035, price is now $726 per person
$726
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,164 reviews)
The staff was very friendly and helpful. There aren't any restaurants within walking distance, but they do have an option to order out that was pretty good. The one thing that surprised me about the room was that the furniture upholstery was somewhat tattered. I don't ever recall seeing that in a Hyatt property before.

Reviewed on Oct 15, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,068, price is now $793 per person
$793
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
The bar downstairs is so fun, and their pizza night provided us with the best pizza in New Haven (better than the famous spots we all know). The bartenders made our trip, and showed us the warmth of the people of New Haven. Do not skip the bar! Even if you do not drink, the games are great and the food is even better.

Reviewed on Oct 17, 2025

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,343, price is now $1,029 per person
$1,029
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.6/10 Exceptional! (54 reviews)
Wonderful property- brand new building, nice spacious rooms perfect for family. Instructors for check in and out and everything in between very clear and helpful.

Reviewed on Oct 15, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $913, price is now $706 per person
$706
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Access to airport and service for my early Lyft was great

Reviewed on Oct 17, 2025

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Prospect Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$98 nightly
The price is $113 total per night from Nov 16 to Nov 17
$113 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,119 reviews)
"The front and interior of the building is beautiful. The back parking lot was a bit overgrown and the rear entry didnt close automatically. Otherwise, a clean, comfortable place to sleep after a long day."

Reviewed on Oct 12, 2025

Holiday Inn Express Southington by IHG
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
Fully refundable
$70 nightly
The price is $81 total per night from Oct 23 to Oct 24
$81 total
Oct 23 - Oct 24
Total with taxes and fees
7/10 Good! (1,017 reviews)
"Easy to get to, clean and affordable. The pizza bar at the end of the property is huge plus. Could use a hair dryer or coffee in the room but considering the price still an excellent choice."

Reviewed on Oct 11, 2025

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
$139 nightly
The price is $160 total per night from Nov 2 to Nov 3
$160 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
"Nice facility overall. A few minor issues in the room that were quickly corrected."

Reviewed on Oct 16, 2025

Trumbull Marriott Shelton
See all 956 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.

Prospect Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
9,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Lake Compounce, Quassy Amusement Park and Toyota Presents Oakdale Theatre

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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 $383 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.

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