Prospect Vacations from $437

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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
Save 100% on your flight
Price was $638, price is now $437 per person
$437
per person
Jan 15 - Jan 20
found 10 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
A really pleasant stay. Easy access to airport, but not so close you are in the flight path.

Reviewed on Nov 2, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $1,083, price is now $889 per person
$889
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,016 reviews)
It was a nice room and hotel but the water in the bathtub was not draining properly even after the maintenance guy came to fix it. We were told there was no note put in that we had an issue at all and that a manager would call us, but we didn’t receive a phone call.

Reviewed on Nov 4, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $957, price is now $791 per person
$791
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
Very happy with my stay here! The staff was super friendly, the coffee shop on property had the most deeeelicious latte that I had throughout my entire trip! Love how the whole property is decorated as well. Very charming!

Reviewed on Nov 6, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Price was $1,160, price is now $978 per person
$978
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The apartment was very clean, well maintained and beautiful decor. The golf simulator was much enjoyed by my son. It's close to the train station, but more of a 20 minute walk to the center of Yale. If you are looking for space and comfort, this is a great place, but just not as close to Yale as other options (though close to Yale medical school).

Reviewed on Sep 16, 2025

Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 out of 5
Price was $813, price is now $691 per person
$691
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (43 reviews)
Clean and comfortable modern room and bed; helpful staff, especially checking in. Pet friendly is great though my pets stay home.

Reviewed on Oct 6, 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
$83 nightly
The price is $95 total per night from Nov 16 to Nov 17
$95 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,144 reviews)
The staff was very nice and professional. The room though, toilet seat was loose, door stopper was hanging off the wall, and the mattresses were EXTREMELY soft. The breakfast was very good though.

Reviewed on Nov 3, 2025

Holiday Inn Express Southington by IHG
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $112 total per night from Dec 2 to Dec 3
$112 total
Dec 2 - Dec 3
Total with taxes and fees
9/10 Wonderful! (1,877 reviews)
Room was clean, hotel staff were friendly, gym was excellent.

Reviewed on Nov 1, 2025

New Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundable
$103 nightly
The price is $119 total per night from Dec 2 to Dec 3
$119 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (959 reviews)
Great hotel. The WiFi didn’t work well but all else was great.

Reviewed on Nov 5, 2025

Cambria Hotel New Haven University Area
See all 962 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.

Find the Best Prospect Vacation Packages

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 $437 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.