Fairfield Vacation Packages

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Your Fairfield Vacation

With every last detail planned before you take off, our Fairfield vacation packages mean you can simply focus on enjoying your getaway. Whether you're based in the neighborhood of Black Rock Historic District, which is good for history, or another area, this exciting city promises a world of discoveries. Ready to explore your surroundings? Fairfield University, Sacred Heart University and Total Mortgage Arena are among the top places to visit during a trip to Fairfield. Don't put off your visit to this destination any longer. The perfect Fairfield vacation is a few clicks away with Expedia.

Top Fairfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
per person
Oct 8 - Oct 11
just found
Roundtrip non-stop flight included
Toronto (YYZ) to New York (LGA)
8/10 Very Good! (1,001 reviews)
Rooms are so cute, art deco type vibe. Rooms are very clean and nice nespresso coffee machine. It was a bummer to see they removed the mini fridges from the rooms amd wish there were a few extra coffee pods, including decaf and extra sugar. Definitely a go to for our trips to Fairfield

Reviewed on Aug. 3, 2025

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
per person
Oct 8 - Oct 11
just found
Roundtrip non-stop flight included
Toronto (YYZ) to New York (LGA)
9/10 Wonderful! (1,396 reviews)
Nicely redecorated rooms. Very spacious and comfortable. Nice breakfast choices. Pool area and outdoor seating was nicely landscaped.

Reviewed on Aug. 1, 2025

Fairfield Beach Vacation

There's nothing like a Fairfield vacation to give yourself a little boost. The soothing melody of rolling surf and the smell of clean ocean air are sure to rejuvenate your mind, body and soul. To be close to the city centre on your trip to Fairfield, base yourself around Jennings Beach (2 kilometres away). If you're intending to hang around a while, consider securing one of our Fairfield packages. Not only will you save some money, you'll also have other stunning beaches around you to explore, like South Pine Creek Beach and Sasco Hill Beach. Now that's a win-win!

Things You Should Know About Fairfield

  • If ocean breezes and strolls along the shore are your idea of a dream vacation, why not opt for one of our Fairfield beach hotels? Staying by the water is the perfect cure for life's daily stresses.
  • Alternatively, browse our range of private vacation homes. They're a hit with travellers planning a stay in Fairfield. Consider Best Western Plus Fairfield Hotel and The Circle Hotel Fairfield.
  • Fairfield has a population of roughly 59,100 people. Why not get out and have a conversation with one or two of them? It's an excellent way to get some inside intel on the place! Also look up our Fairfield things to do page.
  • After you've made some great savings by booking a Fairfield vacation package, you can splurge on unforgettable travel experiences. Sacred Heart University, Fairfield University and Jennings Beach are a few attractions that should be on your must-see list.

Ready to book your vacation to Fairfield?

 

Choose your dates

Fairfield Hotel Deals

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundable
The price is CA $186 per night from Aug 10 to Aug 11
CA $186
CA $214 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,381 reviews)
"Nicely redecorated rooms. Very spacious and comfortable. Nice breakfast choices. Pool area and outdoor seating was nicely landscaped."

Reviewed on Aug. 1, 2025

The Circle Hotel Fairfield
Hotel Hi-Ho - Contactless Check-In

Hotel Hi-Ho - Contactless Check-In

3 out of 5
4180 Black Rock Turnpike, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 13 to Aug 14
CA $134
CA $154 total
Aug 13 - Aug 14
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Rooms are so cute, art deco type vibe. Rooms are very clean and nice nespresso coffee machine. It was a bummer to see they removed the mini fridges from the rooms amd wish there were a few extra coffee pods, including decaf and extra sugar. Definitely a go to for our trips to Fairfield"

Reviewed on Aug. 3, 2025

Hotel Hi-Ho - Contactless Check-In
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

2.5 out of 5
100 Kings Highway Cutoff, Fairfield, CT
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 10 to Aug 11
CA $207
CA $238 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"convient to the amphitheater. Hotel had a musty smell throughout"

Reviewed on Jul. 28, 2025

Best Western Plus Fairfield Hotel
See all 1,293 properties in Fairfield
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Fairfield vacation package cost?
You can snap up a vacation package to this popular destination from CA $626 on Expedia. But how much your vacation to Fairfield costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Fairfield?
You're likely to find reduced prices and better availability in January, February and March. Browse our cheap Fairfield vacation packages and you could get some great off-season discounts.
How many days is enough for Fairfield?
We recommend planning a Fairfield vacation for a minimum of 2 days. This will give you plenty of time to visit top sights such as Total Mortgage Arena and Jennings Beach, as well as check out neighbourhoods like Brooklawn - St. Vincent and Black Rock Historic District. You might even be able to make time for a day trip or two outside of Fairfield.
Is it worth booking a vacation package to Fairfield?
It's no wonder a Fairfield vacation is on the to-do list of many travellers. Popular attractions like Jennings Beach are just the beginning of things to keep you busy here.
How to find the best Fairfield package deals?
Use Expedia's handy filters to help you find some fabulous Fairfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Fairfield package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Fairfield vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights separately. Better still, you can tailor your Fairfield escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Fairfield?
If you have your Fairfield vacation dates locked in, book as soon as you can to snap up some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Fairfield?

  1. Choose your dates: What you plan to do in Fairfield and your preferred season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Fairfield.
  3. Decide how long to go away for: Now that you know more about Fairfield, you can work out the ideal length of your vacation. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Fairfield vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.