Prospect Vacations from $1,348

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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.
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 $1,842, price is now $1,348 per person
$1,348
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
9.6/10 Exceptional! (67 reviews)
The rooms are spacious and clean, kitchen is fully equipped for those who want to cook.

Reviewed on Mar 29, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $4,178, price is now $2,412 per person
$2,412
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $3,315, price is now $2,281 per person
$2,281
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
9.4/10 Exceptional! (349 reviews)
Great service, great stay!!

Reviewed on Apr 7, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $2,340, price is now $1,708 per person
$1,708
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (30 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

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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
$126 nightly
The price is $145 total per night from Apr 16 to Apr 17
$145 total
Apr 16 - Apr 17
Total with taxes and fees
9.2/10 Wonderful! (2,076 reviews)
comfortable beds, clean rooms and general areas, helpful staff, very close to Yale University

Reviewed on Apr 8, 2026

New Haven Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$108 nightly
The price is $124 total per night from Apr 19 to Apr 20
$124 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,263 reviews)
Clean lobby and great hotel staff. Hall way carpets could use a clean

Reviewed on Apr 8, 2026

Holiday Inn Express Southington by IHG
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
$106 nightly
The price is $122 total per night from Apr 19 to Apr 20
$122 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,291 reviews)
The breakfast is excellent. A lot of choices. The room is spacious and clean. The staff are nice.

Reviewed on Apr 6, 2026

Hyatt Place Milford / New Haven
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.

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 $1,348 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.