Fairfield Vacations

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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

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.

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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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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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A river winding through a forested area with houses along the banks.

Tunxis Hill

While there might not be top attractions in Tunxis Hill, you can explore the larger area and discover places like Lake Mohegan Beach and Lake Mohegan.

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Stay near popular Fairfield attractions

A waterfront with docks and a sunset sky.

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.
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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)
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.
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A lake surrounded by trees with autumn foliage, a clear sky, and a hilly landscape in the background.
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.
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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.
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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.
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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.
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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.
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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.
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Fairfield Hotel Deals

The Circle Hotel Fairfield

The Circle Hotel Fairfield

417 Post Road Fairfield CT
Fully refundableReserve now, pay when you stay
$178 nightly
$204 total
Nov 9 - Nov 10
Total with taxes and fees
The Circle Hotel Fairfield
Best Western Plus Fairfield Hotel

Best Western Plus Fairfield Hotel

100 Kings Highway Cutoff Fairfield CT
Fully refundableReserve now, pay when you stay
$159 nightly
$183 total
Nov 24 - Nov 25
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"This property is immaculate! I highly recommend this location."

Reviewed on Oct 21, 2026

Best Western Plus Fairfield Hotel
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
$168 nightly
$193 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Very basic room. It's clean enough. Commons louge for microwave etc. No food outlets on premises. Strictly digital contact to mgmt tho they are responsive. Staircase walk up; limited ground floor rooms. Some background noise from bands playing the bar downstairs."

Reviewed on Oct 24, 2026

Hotel Hi-Ho - Contactless Check-In
See all 1,425 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

Things to do near Fairfield

Fairfield, Connecticut, offers a perfect blend of city and outdoor activities, making it ideal for cultural vacations. You can enjoy spa packages, family day trips, and relaxing weekends, while also exploring recreational areas and golf courses. Dive shows add to the excitement, making it a great destination for both relaxation and fun-filled adventures.

Shopping

The Westport Farmers Market, located 5 miles away, offers a vibrant public market experience with a local flair. For more extensive shopping, the Caldor Shopping Center is 8 miles away with a mix of businesses and family vibes. If you're up for a drive, the Westfield Connecticut Post Mall is 13 miles away, featuring entertainment and a variety of shops for all ages.

Recreation

Experience live events at the Hartford HealthCare Amphitheater, just 4 miles away, where the energetic atmosphere elevates your spirit. For a serene escape, visit Seaside Park, also 4 miles away, to enjoy nature walks and tranquil beachfront relaxation amidst lush greenery.

Adventure

At The Adventure Park at Discovery Museum, located 5 miles from Fairfield, experience thrilling zipline courses among the trees. Wolfe Park Tennis Center, 12 miles away, offers exciting tennis activities. For water sports enthusiasts, Waterski Connecticut, 16 miles from Fairfield, provides an exhilarating aquatic adventure.

Nightlife

Fairfield's nightlife offers a vibrant blend of bars and restaurants. Enjoy cocktails at The Black Rock Tavern or unwind at the casual atmosphere of The Acoustic Café. For live music and a lively crowd, check out The Fairfield Theatre Company.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Fairfield

Fairfield, Connecticut, is perfect for a variety of vacations, whether you're seeking city vibes, outdoor adventures, or cultural experiences. Explore popular attractions like the beautiful beaches, urban parks, and modern universities that cater to families and culture enthusiasts alike. Don't forget to check out Fairfield beach hotels for a comfortable stay while you enjoy all that this charming town has to offer.

  • Jennings Beach: Enjoy the sun and sand at Jennings Beach, a local favorite for its relaxing beach vibes. This scenic spot is perfect for swimming, sunbathing, and picnicking, making it an ideal destination for families and friends looking to unwind by the water.
  • Bridgeport Downtown South Historic District: Immerse yourself in the rich culture of the Bridgeport Downtown South Historic District, located a mere 5 miles from Fairfield. Explore its charming streets, historic architecture, and vibrant local art scene, offering a glimpse into the area's storied past.
  • Total Mortgage Arena: Experience thrilling entertainment at Total Mortgage Arena, just 4 miles from Fairfield. This versatile venue hosts a variety of events, from concerts to sports, providing fun for the entire family and creating unforgettable memories.

Tips to save on your trip to Fairfield

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Fairfield.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

What's included in a Fairfield vacation package?
A Fairfield vacation package typically bundles round-trip flights, hotel stays, and the option to add a rental car for exploring the area. As a beach destination, Fairfield has many hotels located within a few miles of shores like Fairfield Beach. Many properties also provide amenities such as free breakfast and airport shuttle services to and from major hubs like John F. Kennedy International Airport (JFK).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Fairfield vacation package?
When you bundle, you can save up to 30%*. To save money on a Fairfield package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's the best vacation package for Fairfield?
Families looking for the best vacation packages in Fairfield can consider a stay at the 4-star Fairfield Retreat. This property, located about 3 miles from Penfield Beach, offers family rooms, a game room, and kitchens, providing a comfortable and convenient base for your trip.For those seeking value, a Fairfield vacation package with Hotel Hi-Ho - Contactless Check-In is a strong option, costing around $180 per night. Travelers frequently praise this hotel for its great value and super clean rooms, and it includes amenities like free breakfast and a restaurant.Alternatively, The Circle Hotel Fairfield, rated 8.1 out of 10, provides a relaxing stay with an outdoor pool, a bar, and free breakfast. This hotel is about 2 miles from Fairfield Beach, and travelers often highlight its quiet location and convenient overall experience.*Package availability and prices may change depending on dates and demand.
Is Fairfield better suited for a beach vacation or a cultural trip?
Fairfield offers a mix of experiences, making a Fairfield vacation suitable for both beach lovers and those interested in cultural exploration. The destination is characterized as a beach destination outside the city, with several popular spots like Fairfield Beach and Jennings Beach, about 1 and 3 miles from central Fairfield respectively, perfect for coastal relaxation.Beyond the beaches, Fairfield is also known for its cultural attractions. The area has a rich history dating back to the Colonial era and the Revolutionary War, with sites like the Fairfield historic district offering a glimpse into the past. You can explore historic homes and learn about the town's heritage.Ultimately, your Fairfield vacation can be tailored to your preference, whether you prioritize sun and sand or historical discovery.
What's included in a Fairfield beach vacation package?
Fairfield beach vacation packages typically combine flights with a hotel stay, allowing you to explore the area's coastal attractions. While not directly beachfront, hotels like The Circle Hotel Fairfield, rated 8.1 out of 10, offer amenities such as an outdoor pool, free breakfast, and a restaurant, and are located about 2 miles from Fairfield Beach. Travelers frequently praise its nice pool and awesome staff. Another option, Hotel Hi-Ho - Contactless Check-In, about 6 miles from Fairfield Beach, provides free breakfast and a restaurant, with travelers often highlighting its modern rooms and friendly staff. Your Fairfield vacation package can be customized to include various hotel options, but specific inclusions like meals, drinks, or water sports depend on the chosen hotel and rate. Excursions and activities are generally separate unless explicitly bundled.
What are the top things to do in Fairfield?
A Fairfield vacation offers a variety of activities, from relaxing on the sand to enjoying live entertainment:Browse and book things to do in Fairfield on Expedia.
Do you need to rent a car in Fairfield, or is public transport enough?
For Fairfield vacation packages with flights, a rental car offers the most flexibility, especially for exploring the area's beaches and urban attractions. While Fairfield is served by public transport, including three Metro-North Railroad stations and public bus lines of the Greater Bridgeport Transit Authority, a car makes it easier to reach various points of interest at your own pace.Fairfield is accessible from several major airports, including John F. Kennedy International Airport (JFK), Newark Liberty International Airport (EWR), LaGuardia Airport (LGA), Bradley International Airport (BDL), and Westchester County Airport (HPN). Having a car allows for convenient travel to and from these airports and for day trips to nearby towns or natural areas, enhancing your Fairfield vacation package experience.
Are Fairfield vacation package hotels conveniently located?
Fairfield vacation package hotels are generally conveniently located, with many properties within easy reach of central Fairfield and its attractions.For example, The Circle Hotel Fairfield is about 1 mile from central Fairfield, while Best Western Plus Fairfield Hotel is about 2 miles away. Even properties like Hotel Hi-Ho - Contactless Check-In are about 4 miles from the city center. This means you can often find a hotel that keeps you close to the heart of the action or a short drive from the beaches.
Can I change or cancel my Fairfield vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Fairfield vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Fairfield vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Fairfield vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Fairfield?
To find last-minute vacation packages to Fairfield, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Fairfield vacation packages?
Free cancellation on a Fairfield vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Fairfield vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Fairfield getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Fairfield vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.