Prospect Vacations from $258

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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.
Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

3 out of 5
Price was $288, price is now $258 per person
$258
per person
Mar 18 - Mar 21
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.4/10 Very Good! (1,000 reviews)
Staff, Room and Location

Reviewed on Jan 24, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,495, price is now $1,703 per person
$1,703
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
No reviews

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Price was $808, price is now $651 per person
$651
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Price was $942, price is now $823 per person
$823
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
9.4/10 Exceptional! (336 reviews)
beautiful room and views

Reviewed on Dec 13, 2025

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

3.5 out of 5
Price was $417, price is now $375 per person
$375
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Clean and convienant for families . There are restaurants walking distance . Only thing was there were no microwaves in the room. Would still visit again enjoyed the pool and hot tub .

Reviewed on Jan 19, 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
$106 nightly
The price is $122 total per night from Feb 8 to Feb 9
$122 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (2,013 reviews)
The room was spotless, all of the staff were accommodating and friendly.

Reviewed on Jan 27, 2026

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
$107 nightly
The price is $123 total per night from Feb 22 to Feb 23
$123 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
Room matched pictures. Front desk people were excey

Reviewed on Jan 21, 2026

Cambria Hotel New Haven University Area
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $136 total per night from Feb 8 to Feb 9
$136 total
Feb 8 - Feb 9
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
Wonderful

Reviewed on Jan 26, 2026

Trumbull Marriott Shelton
See all 1,044 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 $258 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.