Fairfield Holiday Rentals

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Our top choices for Fairfield holiday rentals

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
10.0 out of 10, Exceptional, (11)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is NZ$820
includes taxes & fees
4 Jan - 5 Jan 2026
Bright Escape, Top-Rated Design, Fire pit, Near Beach
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is NZ$541
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
10.0 out of 10, Exceptional, (2)
"Wonderful "
United States
Nolufefe Z.
The price is NZ$637
includes taxes & fees
12 Jan - 13 Jan 2026
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
10.0 out of 10, Exceptional, (22)
"Great family home. Location is perfect, close to everything yet private and quiet. "
United States
Margaret W.
The price is NZ$814
includes taxes & fees
6 Jan - 7 Jan 2026
Top Rated Gem, Fire Pit, Near Beach, Fairfield U, 90 min to NYC
10.0 out of 10, Exceptional, (1)
"The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. "
United States
Patricia B.
The price is NZ$4,009
includes taxes & fees
5 Jan - 6 Jan 2026
🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is NZ$305
includes taxes & fees
29 Dec - 30 Dec
Charming Studio| Near Yale| Downtown New Haven
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is NZ$354
includes taxes & fees
4 Jan - 5 Jan 2026
One bedroom apartment in United States of America, New Haven
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is NZ$579
includes taxes & fees
25 Dec - 26 Dec
Angelica’s safe haven @ west haven

Apartment in West New Haven

The Nest At Elm City Flats.
9.4 out of 10, Exceptional, (6)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
The price is NZ$403
includes taxes & fees
6 Jan - 7 Jan 2026
The Nest At Elm City Flats.
3.0 star property
The price is NZ$613
includes taxes & fees
5 Jan - 6 Jan 2026
2 Mi to Beach, Shared Yard Space: West Haven Apt!

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is NZ$482
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is NZ$331
includes taxes & fees
29 Dec - 30 Dec
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
9.4 out of 10, Exceptional, (3)
"The place was so cozy and perfect for a lil getaway so many places nearby!"
United States
Luis R.
The price is NZ$328
includes taxes & fees
28 Dec - 29 Dec
Downtown loft apartment in the heart of downtown New Haven.
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is NZ$404
includes taxes & fees
8 Jan - 9 Jan 2026
Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (4)
"Great place - wish we had more than one night. "
United States
Steri-Clean N.
The price is NZ$644
includes taxes & fees
5 Jan - 6 Jan 2026
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
The price is NZ$351
includes taxes & fees
6 Jan - 7 Jan 2026
Yale Casa Verde Studio
9.6 out of 10, Exceptional, (7)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
United States
Caroline
The price is NZ$390
includes taxes & fees
25 Dec - 26 Dec
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Cottage in Miller Place

Cozy Country Cottage #4
10.0 out of 10, Exceptional, (15)
"Lovely cottage with great host! All was wonderful!! very happy with our 17 day vacation!"
United States
Laurita S.
The price is NZ$557
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Country Cottage #4
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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Top Fairfield Hotel Reviews

Find out more about Fairfield

Everything you need to know about Fairfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fairfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fairfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Fairfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fairfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fairfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fairfield holiday rentals we have selected for you start as low as NZ$217 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Fairfield rentals

At Expedia, we put the best Fairfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fairfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fairfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fairfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Fairfield?

Yes, there are holiday rentals in Fairfield close to Connecticut Audubon Birdcraft Museum, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Fairfield is known for its shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Fairfield has to offer?

Charming 3-bedroom house with WiFi, AC in serene Fairfield: This highly rated holiday home rental in Fairfield is equipped with a BBQ, air conditioning and a Smart TV to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Fairfield?

With 57 Expedia holiday rentals, you're guaranteed to find just the right place for your Fairfield stay.

What can I see and do in Fairfield?

Enjoy the outdoors at Penfield Beach and Fairfield Beach, or simply take in cultural attractions like Fairfield Theater Company and Fairfield Museum and History Center. Jennings Beach and Lake Mohegan are other places to visit while you're in town.

What are holiday rentals like in Fairfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Fairfield. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for families.