Prospect Vacation Packages
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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.
Top Prospect Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Cambria Hotel New Haven University Area
West River
Price was CA $953, price is now CA $854 per person
CA $854
per person
Apr 16 - Apr 20
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
Room matched pictures. Front desk people were excey
Reviewed on Jan 21, 2026
Clarion Inn
Price was CA $868, price is now CA $782 per person
CA $782
per person
Apr 16 - Apr 20
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
7.6/10 Good! (1,002 reviews)
Not very clean, there was a towel and other miscellaneous things under one of the beds. It was advertised as 2 queens and it was really 2 full size mattresses. Staff was friendly otherwise
Reviewed on Feb 1, 2026
Comfort Inn Naugatuck-Shelton, CT
Price was CA $914, price is now CA $852 per person
CA $852
per person
Apr 16 - Apr 20
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
7.8/10 Good! (729 reviews)
Everything was great and the price matched. I am a nurse and had to stay through the storm.
Reviewed on Jan 28, 2026
Prospect Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundable
The price is CA $156 per night from Feb 15 to Feb 16
CA $156
CA $179 total
Feb 15 - Feb 16
includes taxes & fees
9/10 Wonderful! (2,016 reviews)
Excellent desk staff. Clean and quite room. Good location.
Reviewed on Feb 4, 2026
Cambria Hotel New Haven University Area
20 Dwight Street New Haven CT
Fully refundable
The price is CA $141 per night from Mar 8 to Mar 9
CA $141
CA $162 total
Mar 8 - Mar 9
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
Lovely
Reviewed on Feb 3, 2026
Motel 6 Milford, CT
111 Schoolhouse Road Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Feb 18 to Feb 19
CA $81
CA $94 total
Feb 18 - Feb 19
includes taxes & fees
6.2/10 (1,005 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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
