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.

Where to stay in Fairfield

Find the best Fairfield areas and neighborhoods for the activities you enjoy most. Learn more about Fairfield
A lighthouse at night with a full moon in the sky.

Fairfield Beach

4 out of top 10 points of interest in this area

If you're spending some time in Fairfield Beach, Penfield Beach and Fairfield Beach are top sights worth seeing.

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Fairfield Center

2 out of top 10 points of interest in this area

While visiting Fairfield Center, you might make a stop by sights like Fairfield Theater Company and Connecticut Audubon Birdcraft Museum.

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Grasmere

Grasmere might not have many top sights, but Jennings Beach and Fairfield Theater Company are two attractions nearby that you can check out.

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Sasco

1 out of top 10 points of interest in this area

While visiting Sasco, you might make a stop by sights like Country Club of Fairfield and South Pine Creek Beach.

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Greenfield Hill

The beaches and parks are a few reasons travelers visit Greenfield Hill. Though there aren't many top sights in the neighborhood, you can visit Lake Mohegan Beach and Lake Mohegan, a few notable attractions nearby.

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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?

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Fairfield Hotel Deals

The Circle Hotel Fairfield

The Circle Hotel Fairfield

417 Post Road Fairfield CT
Fully refundable
CA $177
CA $218 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (1,480 reviews)
"Hhh"

Reviewed on Aug 15, 2026

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

Hotel Hi-Ho - Contactless Check-In

4180 Black Rock Turnpike Fairfield CT
Fully refundableReserve now, pay when you stay
CA $164
CA $202 total
Sep 2 - Sep 3
includes taxes & fees
Hotel Hi-Ho - Contactless Check-In
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

100 Kings Highway Cutoff Fairfield CT
Fully refundableReserve now, pay when you stay
CA $236
CA $271 total
Aug 17 - Aug 18
includes taxes & fees
Best Western Plus Fairfield Hotel
See all 1,427 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.
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Stay near popular Fairfield attractions

A waterfront with docks and a sunset sky.

Fairfield Beach

8.6/10 (34 reviews)
Why not spend a lazy afternoon at Fairfield Beach during your trip to Fairfield?
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A calm lake with autumn-colored trees reflecting on the water.
Photo by Eva Perez Castro

Lake Mohegan

8.2/10 (10 reviews)
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.
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Jennings Beach

9.0/10 (80 reviews)
If a restful vacation is part of your travel plans, Jennings Beach might be the perfect place to seek out during your trip to Fairfield. Stroll along the waterfront or discover the area's sunsets.
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Penfield Beach

9.0/10 (38 reviews)
Why not spend a carefree afternoon at Penfield Beach during your travels in Fairfield? Discover the sunsets while you're in the area.
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Fairfield Theater Company

8.8/10 (15 reviews)
You can make plans for a show at Fairfield Theater Company during your trip to Fairfield. While you're in the area, stroll along the beautiful beaches.
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Country Club of Fairfield

8.0/10 (9 reviews)
Enjoy a round of golf in Fairfield at Country Club of Fairfield. While you're in the area, stroll along the beautiful beaches.
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South Pine Creek Beach

9.0/10 (2 reviews)
Why not spend a lazy afternoon at South Pine Creek Beach during your trip to Fairfield?
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Fairfield Museum and History Center

You can spend an afternoon browsing the exhibits at Fairfield Museum and History Center in Fairfield. While you're in the area, stroll along the beautiful beaches.
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Frequently asked questions

How much does a Fairfield vacation package cost?
You can snap up a vacation package to this popular destination 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.