Fairfield Vacations

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Find the Best Fairfield Vacation Packages

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 center on your trip to Fairfield, base yourself around Jennings Beach (2 kilometers 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 travelers 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.

Fairfield Hotel Deals

The Circle Hotel Fairfield
The Circle Hotel Fairfield
3 out of 5
417 Post Road, Fairfield, CT
Fully refundable
8.8/10 Excellent! (1,376 reviews)
"Clean"

Reviewed on Jun 19, 2025

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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
7.8/10 Good! (1,000 reviews)
"I use a cane and not having help to bring in my suitcase was a problem Needed some of my family to come from their home to help me. Also could not get any ice which I need for my knee.VMR"

Reviewed on Jun 16, 2025

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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 ₩205,558 per night from Jun 29 to Jun 30
₩205,558
₩236,394 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Nice"

Reviewed on Jun 20, 2025

Best Western Plus Fairfield Hotel
See all 1,285 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.

Frequently asked questions

How much does a Fairfield vacation package cost?
You can grab a vacation package to this destination on Expedia. However, how much your vacation to Fairfield costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Fairfield?
You can generally find lower rates and greater availability in January, February and March. Check out our cheap Fairfield vacation packages and you could score some great off-season deals.
How many days is enough for Fairfield?
We recommend booking a Fairfield vacation for around 2 days. This will allow you time to tick off top sights such as South Pine Creek Beach and Sasco Hill Beach, as well as check out neighborhoods like Brooklawn - St. Vincent and Black Rock Historic District. You could even fit in a day trip or two outside of Fairfield.
Is it worth booking a vacation package to Fairfield?
Fairfield offers everything you need for an unforgettable escape. Begin your Fairfield vacation on a high note by checking out major attractions like Jennings Beach.
How to find the best Fairfield package deals?
Finding a cheap Fairfield package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Fairfield package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Fairfield vacation as a package?
You can enjoy significant savings on your Fairfield getaway by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Fairfield?
If you're planning a spur-of-the-moment Fairfield trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Fairfield?

  1. Choose when to go: Check your schedule and get packing. Your favorite time of year and the available activities will also help you decide when to escape to Fairfield.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your hotel will likely be the largest expense during your trip to Fairfield.
  3. Decide how long to go away for: Now that you're up to speed on Fairfield, you can figure out the ideal length of your vacation. Pull together a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Fairfield vacation package.

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