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 Southington

Courtyard by Marriott Southington

3 out of 5
Price was $304, price is now $258 per person
$258
per person
Nov 14 - Nov 16
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (432 reviews)
The rooms were clean and the area was nice as well. Would stay again.

Reviewed on Sep 1, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,915, price is now $1,809 per person
$1,809
per person
Nov 28 - Dec 3
found 6 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Price was $1,051, price is now $824 per person
$824
per person
Nov 21 - Nov 24
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9.4/10 Exceptional! (314 reviews)
Like always, everyone and everything was just perfect ! Thank you all for always making our stay wonderful !

Reviewed on Sep 15, 2025

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $898, price is now $731 per person
$731
per person
Nov 28 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Very clean room! Staff were friendly and knowledgeable about the area!

Reviewed on Sep 13, 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 $299, price is now $259 per person
$259
per person
Nov 14 - Nov 16
found 19 hours ago
Roundtrip flight included
Orlando (MCO) 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

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Prospect Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
$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! (1,760 reviews)
"Friendliest staff!"

Reviewed on Sep 10, 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! (1,000 reviews)
"I have stayed at this Marriot before a couple years back and within that time I feel some disrepair has fallen on the property. The landscaping, cleanliness, as well as staff has always been more than adequate. However I found the condition of the parking lot and the main entrance are in dire need ..."

Reviewed on Sep 7, 2025

Trumbull Marriott Shelton
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Oct 5 to Oct 6
$183 total
Oct 5 - Oct 6
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"Beautiful building nice people, outstanding location"

Reviewed on Sep 9, 2025

Omni New Haven Hotel at Yale
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 $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.

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.