Fairfield Vacations from $451

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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.

The Latest Fairfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
Price was $588, price is now $451 per person
$451
per person
Dec 16 - Dec 20
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to New York (LGA)
9/10 Wonderful! (1,394 reviews)
The room was nice , clean but dated. I didn’t have breakfast

Reviewed on Oct 20, 2025

DUNE Fairfield Beach

DUNE Fairfield Beach

3 out of 5
Price was $593, price is now $495 per person
$495
per person
Dec 11 - Dec 14
found 5 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to New York (LGA)
9/10 Wonderful! (73 reviews)
Incredible staff, friendly, helpful.

Reviewed on Jun 29, 2025

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Discover the most popular places to visit in Fairfield

Jennings Beach

4.5/5(3 reviews)

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

Penfield Beach

If a restful vacation is part of your travel plans, Penfield Beach might be the perfect place to seek out during your trip to Fairfield. Visit the shops in this family-friendly area, or simply enjoy its restaurants.

Penfield Beach

Fairchild Wheeler Golf Course

Enjoy a round of golf in Fairfield at Fairchild Wheeler Golf Course. Stroll along the beautiful beaches or attend a sporting event in this family-friendly area.

Fairchild Wheeler Golf Course

Fairfield Hotel Deals

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Nov 9 to Nov 10
$183 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (1,399 reviews)
"We love staying here! Such a great location and always 100% clean! The breakfast is excellent too!"

Reviewed on Oct 19, 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
$135 nightly
The price is $155 total per night from Nov 2 to Nov 3
$155 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,014 reviews)
"Clean and friendly staff"

Reviewed on Oct 11, 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
$150 nightly
The price is $172 total per night from Oct 26 to Oct 27
$172 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (1,009 reviews)
"This is a smaller hotel which made it much easier for me. Not many stairs and everything very close in vicinity. Felt safe, definitely clean. Little noisy since it’s right off the highway, but I didn’t mind it."

Reviewed on Oct 17, 2025

Best Western Plus Fairfield Hotel
See all 1,313 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.

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 (1 mile 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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Westchester County Airport (HPN)
Population
59,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Jennings Beach, Norwalk Maritime Aquarium and Compo Beach

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Frequently asked questions

How much does a Fairfield vacation package cost?
You can grab a vacation package to this destination from $451 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?
If you'd like to snag a cheap Fairfield vacation package, consider visiting in November, December and January. You'll usually find better rates on flights and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Fairfield?
We recommend planning a Fairfield vacation for at least 2 days. This will give you enough time to visit key attractions including South Pine Creek Beach and Sasco Hill Beach, and check out neighborhoods like Black Rock Gardens Historic District and Black Rock Historic District. You could even fit in a day trip from Fairfield.
Is it worth booking a vacation package to Fairfield?
Fairfield is a good vacation destination with attractions like Jennings Beach among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Fairfield vacation promises fun for everyone.
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.
Does Expedia offer Book Now, Pay Later Fairfield vacation packages?
Secure your dream trip to Fairfield with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up cheap deals while they last.

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