Prospect Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
CA $1,133
per person
Oct 16 - Oct 19
found 20 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
8/10 Very good! (1,009 reviews)
Our unit had spider webs on the ceiling. Bed was short sheeted. We had to remake the bed ourselves. Nonexistent Wi-Fi connection. One bar. Kept disconnecting. One ice machine was working for all units.
Staff was nice. Helpful. Upstairs chambermaid came down to remove the spider webs. We appreciated her quick response. Will not return on future visits to the area.
Reviewed on Aug 14, 2026
The Scranton Seahorse Inn
Madison Center
CA $1,568
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9/10 Wonderful! (245 reviews)
Excellent B&B. Great breakfast. Lovely area. Walk around to local stores and restaurants. And beach is nearby.
Reviewed on Aug 1, 2026
Madison Beach Hotel
Madison Center
CA $3,154
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9.4/10 Exceptional! (379 reviews)
The whole experience was fantastic. Very relaxed atmosphere.with a gorgeous beach view from the hotel room .
Reviewed on Aug 13, 2026
Ready to book your vacation to Prospect?
Prospect Hotel Deals
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
CA $88
CA $102 total
Sep 3 - Sep 4
includes taxes & fees
7.2/10 Good! (1,002 reviews)
"I personally think that this hotel was very good for the price. Although I personally thought that the WiFi was not good, took me several tries to upload some pictures I needed to upload and even worked better in some parts of the room than others. Also wish the WiFi was secure. Plus the hotel is ..."
Reviewed on Aug 15, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $207
CA $238 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Zack (Restaurant) was amazing. My stay didn’t start off too well, but Zack changed that. He was personable yet professional. Great personality!! Wish our paths crossed at the end, I would have loved to say goodbye."
Reviewed on Aug 13, 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
CA $158
CA $181 total
Aug 23 - Aug 24
includes taxes & fees
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.
Frequently asked questions
How much does a Prospect vacation package cost?
You'll find cheap prices from CA $1,133 on Expedia for your Prospect break. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Prospect costs.
What are the cheapest months to go to Prospect?
January, February and March are the best times to look for cheap Prospect vacation packages. Choosing to travel in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Prospect?
Typically, a few days is great for a Prospect vacation. With a carefully crafted itinerary, you can go to all the top attractions including Holy Land USA, as well as discover some hidden treasures along the way.
How to find the best Prospect package deals?
Start your search for a Prospect package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Prospect package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Prospect adventure underway.
Is it cheaper to book a Prospect vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can customize your Prospect getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Prospect?
If you're planning a spur-of-the-moment Prospect getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Prospect?
- Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Prospect.
- Budget wisely: In addition to the cost of your hotel, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Prospect.
- Decide how long to go away for: Now that you're more familiar with Prospect, you can figure out the perfect length of your break. Pull together a rough plan and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored Prospect vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
