Prospect Vacations from $231

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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.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was $289, price is now $231 per person
$231
per person
May 21 - May 24
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (755 reviews)
Clean room, comfy bed

Reviewed on Feb 16, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,175, price is now $865 per person
$865
per person
May 21 - May 24
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Loved the location and the room!

Reviewed on Feb 23, 2026

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $1,880, price is now $1,419 per person
$1,419
per person
May 17 - May 19
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The place could have been a little cleaner I found hair in the bed and crumbs and dirt in the couch and under it as well the walls were stained and the carpet was stained in the bedroom it definitely was a big difference from the first time I stayed there

Reviewed on Feb 16, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $450, price is now $362 per person
$362
per person
May 21 - May 24
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,184 reviews)
Place was great highly recommend

Reviewed on Feb 25, 2026

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $494, price is now $406 per person
$406
per person
May 17 - May 19
found 5 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
everything in the hotel was amazing until the night staff arrived i went down to ask for another roll of toilet paper and he said he couldn’t go get any and told us we could use the downstairs lobby bathroom if we needed to use it

Reviewed on Feb 24, 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
$97 nightly
The price is $112 total per night from Mar 22 to Mar 23
$112 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (2,024 reviews)
Clean room and courteous staff provided professional service

Reviewed on Feb 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
$114 nightly
The price is $131 total per night from Mar 22 to Mar 23
$131 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
Hotel was clean and close to the hospital

Reviewed on Feb 27, 2026

Cambria Hotel New Haven University Area
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
$149 nightly
The price is $171 total per night from Mar 8 to Mar 9
$171 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
The area is run down and it’s a hectic environment but the bed and pillows were very comfortable and the price was reasonable for a Friday night at the Shubert. Walking distance to the theatre and wonderful dinner at Luke so it was a lovely evening.

Reviewed on Mar 1, 2026

Omni New Haven Hotel at Yale
See all 1,068 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 $231 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.