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.
Water's Edge Resort & Spa
Westbrook Center
$629
per person
Dec 10 - Dec 13
found 21 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Beautiful property.The staff were very accommodating ,helpful and friendly.The only complaint to report was the lack of on site eating facilities .We arrived on a rainy Sunday and the outside venue for lunch was closed.The bar did not serve food until 3:30.The only option was the Sunday buffet which was priced at $59.00pp.Starbucks was limited to a grilled cheese or a ham egg sandwich.We were forced to leave the property to have lunch . The espresso martini was priced at &20.00 a tad high .Overall it was an enjoyable stay.
Reviewed on Sep 22, 2026
Head of Pond House
$658
per person
Dec 10 - Dec 13
found 21 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
10/10 Exceptional! (13 reviews)
Excellent European B&B experience not often found in the States. A quaint well-managed property with hidden charm. The bedrooms were spacious , comfortable and
nicely designed with taste and simplicity.
Reviewed on Sep 20, 2026
Hyatus Luxury Residences City Crossing
The Hill
$604
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Prospect Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$133 nightly
$153 total
Sep 29 - Sep 30
Total with taxes and fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
$110 nightly
$126 total
Oct 7 - Oct 8
Total with taxes and fees
8.2/10 Very Good! (1,858 reviews)
"The room had hairs on the toilet and in the sink. The toilet was not flushing down and the shower was not draining so it filled up as we took a shower. The staff at night was goofing off behind the counter with several women flirting with a young man sitting there. We will not stay here again."
Reviewed on Sep 21, 2026
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.
