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! (1,385 reviews)
First Choice
"This is my Go-To / First Choice when visiting the Fairfield area. Rooms are always clean & immaculate + very comfy bed, great towels, good size room...and traveling alone I feel safe! Staff is so welcoming and extra helpful. Keep it up."

Reviewed on 2025/8/7

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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! (1,001 reviews)
"Excellent"

Reviewed on 2025/8/5

Get rates
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 NT$4,464 per night from Aug 24 to Aug 25
NT$4,464
NT$5,134 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"convient to the amphitheater. Hotel had a musty smell throughout"

Reviewed on 2025/7/28

Best Western Plus Fairfield Hotel
See all 1,302 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.

Discover the most popular places to visit in Fairfield

Nice lake, gorgeous all year long.

Lake Mohegan

Commune with nature and explore the great outdoors at Lake Mohegan during your travels in Fairfield. Stroll along the beaches or visit the shops in this family-friendly area.

Lake Mohegan

Fairfield University

Take a campus tour or just explore the area of Fairfield University, during your travels in Fairfield. Stroll along the area's beautiful beaches, or simply savor its top-notch restaurants.

Fairfield University

Jennings Beach

Why not spend a carefree afternoon at Jennings Beach during your travels in Fairfield? Visit the shops in this family-friendly area, or simply enjoy its restaurants.

Jennings Beach

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.