Fairfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Tim Rousseau

Top hotels in Fairfield

The Circle Hotel Fairfield

The Circle Hotel Fairfield

3 out of 5
417 Post Road, Fairfield, CT
Fully refundable
8.8/10 Excellent! (1,386 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 7 Aug 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! (1,006 reviews)
"Everything"

Reviewed on 8 Aug 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 3.932.888 ₫ per night from 17 Aug to 18 Aug
3.932.888 ₫
4.522.861 ₫ total
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"convient to the amphitheater. Hotel had a musty smell throughout"

Reviewed on 28 Jul 2025

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.

Popular places to visit

Lake Mohegan

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 savour its top-notch restaurants.

Fairfield University

Country Club of Fairfield

Enjoy a round of golf in Fairfield at Country Club of Fairfield. While you're in the area, stroll along the beautiful beaches.

Country Club of Fairfield

Frequently asked questions

How much does a Fairfield holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday 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 holiday packages and you could score some great off-season deals.
How many days is enough for Fairfield?
We recommend booking a Fairfield holiday 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 neighbourhoods 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 holiday package to Fairfield?
Fairfield offers everything you need for an unforgettable escape. Begin your Fairfield holiday 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 customise 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 holiday as a package?
You can enjoy significant savings on your Fairfield getaway by booking a tailored holiday 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 holiday 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 favourite 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 holiday. 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 holiday package.