Fairfield Vacations
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Where to stay in Fairfield
Find the best Fairfield areas and neighborhoods for the activities you enjoy most. Learn more about Fairfield
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.
Fairfield Center
1 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.
Grasmere
Grasmere might not have many top sights, but Jennings Beach and Fairfield Theater Company are two attractions nearby that you can check out.
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.
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.
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
417 Post Road Fairfield CT
Fully refundable
NT$4,305
NT$5,269 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (1,489 reviews)
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Reviewed on 2026/8/18
Hotel Hi-Ho - Contactless Check-In
4180 Black Rock Turnpike Fairfield CT
Fully refundableReserve now, pay when you stay
NT$3,795
NT$4,683 total
Aug 19 - Aug 20
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"Easy in, easy out. Great proximity to the highway and love that Barcelona (restaurant) is attached"
Reviewed on 2026/8/16
Best Western Plus Fairfield Hotel
100 Kings Highway Cutoff Fairfield CT
Fully refundableReserve now, pay when you stay
NT$5,125
NT$5,894 total
Sep 13 - Sep 14
includes taxes & fees
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.
Stay near popular Fairfield attractions
Fairfield Beach
8.6/10 (34 reviews)
Stretch out along five miles of pristine Long Island Sound shoreline at Fairfield Beach. Collect seashells, watch sailboats drift by, and enjoy the gentle waves perfect for family swimming.
Photo by Eva Perez Castro
Lake Mohegan
8.2/10 (10 reviews)
This scenic man-made lake offers a sandy beach and designated swimming areas perfect for family outings. Explore surrounding woodland trails or enjoy the children's sprinkler park during summer months.
Photo by Eva Perez Castro
Lake Mohegan Beach
9.0/10 (4 reviews)
This freshwater oasis in Fairfield features a sandy beach with lifeguarded swimming areas and hiking trails. Enjoy the recreation area with its sprinkler park, playground, and picnic spots perfect for family outings.
Jennings Beach
9.0/10 (80 reviews)
Jennings Beach offers expansive sandy shores along Long Island Sound with a family-friendly atmosphere. Enjoy summer concerts and movie nights on the beach, or simply relax with picturesque coastal views.
Penfield Beach
9.0/10 (38 reviews)
This 3.5-acre Long Island Sound beach offers a serene escape with sandy shores and calm waters. Enjoy family picnics at designated areas with grills or let children play at the beachfront playground.
Fairfield Theater Company
8.8/10 (15 reviews)
This intimate venue hosts diverse concerts, theater, and comedy in two distinct spaces. Enjoy emerging artists and established acts in StageOne's close-up setting or The Warehouse's industrial-chic atmosphere.
South Pine Creek Beach
9.0/10 (2 reviews)
This tranquil shoreline along Long Island Sound offers a peaceful escape from Connecticut's busier beaches. Enjoy sunbathing or swims in its calm waters, though summer parking requires a resident beach sticker.
Country Club of Fairfield
8.0/10 (9 reviews)
This historic Seth Raynor-designed course features a classic links-style layout with stunning Long Island Sound views. Members enjoy a challenging round shaped by coastal winds and traditional golfing principles.
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?
- 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.
- 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.
- 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.
- 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.
