Prospect Vacations from $232

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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 $258, price is now $232 per person
$232
per person
Mar 15 - Mar 18
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
Room was clean and warm and the staff was very friendly

Reviewed on Feb 1, 2026

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was $536, price is now $464 per person
$464
per person
Mar 15 - Mar 18
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
It was perfect for an evening away, quiet, friendly staff, beautiful views, and great Sunday brunch

Reviewed on Dec 29, 2025

Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
Westbrook Center
Price was $430, price is now $398 per person
$398
per person
Mar 15 - Mar 18
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.8/10 Exceptional! (175 reviews)
Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :)

Reviewed on Dec 21, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Price was $748, price is now $725 per person
$725
per person
Mar 15 - Mar 18
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (1,001 reviews)
Very comfortable and enjoyable place to stay.

Reviewed on Feb 2, 2026

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2 out of 5
Price was $429, price is now $417 per person
$417
per person
Apr 2 - Apr 5
just found
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
7.2/10 Good! (459 reviews)
All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it.

Reviewed on Jan 4, 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
$126 nightly
The price is $145 total per night from Feb 22 to Feb 23
$145 total
Feb 22 - Feb 23
Total with taxes and fees
9/10 Wonderful! (2,014 reviews)
Room was a safe haven during a bad winter storm. The front desk attendant - I believe his name was Suvar was incredibly kind and accommodating - let us know the only place that was open and where we could get a hot meal after a 12 hour shift in the hospital.

Reviewed on Jan 29, 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 Mar 1 to Mar 2
$123 total
Mar 1 - Mar 2
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Nice fromt desk staff. Clean & comfortable room.

Reviewed on Jan 26, 2026

Cambria Hotel New Haven University Area
Motel 6 Milford, CT

Motel 6 Milford, CT

2 out of 5
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $75 total per night from Feb 22 to Feb 23
$75 total
Feb 22 - Feb 23
Total with taxes and fees
6.2/10 (1,007 reviews)
My room was immaculate and the staff were very kind and easy to work with check-in was a breeze. It’s a good location near to stores and restaurants. It was very affordable. The shower pressure was great. Everything was great. The beds were comfortable. Sheets white and fresh. As a student, this ...

Reviewed on Jan 31, 2026

Motel 6 Milford, CT
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 $232 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.