Prospect Vacations from $414

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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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $564, price is now $414 per person
$414
per person
Jul 24 - Jul 27
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,000 reviews)
Comfortable for a nights stay. Close to nice restaurants and shopping.

Reviewed on May 21, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,432, price is now $913 per person
$913
per person
Jul 11 - Jul 13
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
No reviews
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $979, price is now $763 per person
$763
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $1,055, price is now $826 per person
$826
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
9.6/10 Exceptional! (73 reviews)
I had a great stay at this property overall. The room was clean, comfortable, and well-maintained, which made it easy to relax after a long day. The staff was friendly and helpful, always willing to answer questions and make sure everything was taken care of. The kitchen was stocked with the basics needed for cooking, which was convenient during the stay. Parking was also easy to access and felt safe, which was a big plus. The location was convenient, close to nearby attractions, restaurants, and stores. If I had to mention one thing for improvement, it would be minor updates to some areas to make the space feel a bit more modern. Overall, I would definitely recommend this property and would consider staying here again in the future.

Reviewed on May 5, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $835, price is now $670 per person
$670
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
No reviews
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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
$132 nightly
The price is $152 total per night from Jun 7 to Jun 8
$152 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (2,142 reviews)
"Front desk staff made my check in quick and easy, answered my questions re: parking w/o issue. Since we arrived after 8pm, I really appreciated the security of the parking garage across the street (gated w/ key card access) and the ease of getting to the hotel from the sky bridge. The room was clean ..."

Reviewed on May 27, 2026

New Haven Hotel
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
$112 nightly
The price is $129 total per night from Jun 21 to Jun 22
$129 total
Jun 21 - Jun 22
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"The bathroom was too small. The coffee maker didn’t work well."

Reviewed on May 27, 2026

Omni New Haven Hotel at Yale
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$117 nightly
The price is $135 total per night from Jun 28 to Jun 29
$135 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (1,309 reviews)
"The staff was welcoming and friendly. The property was very clean, my only problem(s) was the room smelled like smoke for a non smoking room. The other problem was the mold on the ceiling in the bathroom it’s not healthy. It was a good stay for what it was needed for a weekend stay to spend time ..."

Reviewed on May 26, 2026

Holiday Inn Express Southington by IHG
See all 1,112 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 $414 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.