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Fairfield Holiday Rentals

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Our top choices for Fairfield holiday rentals

1. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NZ$460
includes taxes & fees
6 Dec - 7 Dec
DUNE Fairfield Beach

2. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
Tunxis Hill
10.0 out of 10, Exceptional, (2 reviews)
"Host was attentive and the space was comfortable and exactly what we needed"
United States
Parker M.
The price is NZ$592
includes taxes & fees
9 Nov - 10 Nov
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

3. Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
West End - West Side
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay "
United States
Maria Elena G.
The price is NZ$644
includes taxes & fees
9 Nov - 10 Nov
Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch

4. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (41 reviews)
"Great accommodations and perfect location for us. "
United States
Kim G.
The price is NZ$1,019
includes taxes & fees
15 Nov - 16 Nov
Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

5. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
Fairfield
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."
United States
Tara C.
The price is NZ$976
includes taxes & fees
9 Nov - 10 Nov
Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

6. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is NZ$1,646
includes taxes & fees
8 Nov - 9 Nov
4 Mi to Beach & Dtwn! Charming Fairfield Home

7. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious
Tunxis Hill
9.6 out of 10, Exceptional, (21 reviews)
"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "
United States
Emily K.
The price is NZ$1,363
includes taxes & fees
9 Nov - 10 Nov
Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

8. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
Tunxis Hill
6.0 out of 10, (2 reviews)
"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."
United States
Raelyn O.
The price is NZ$1,521
includes taxes & fees
8 Nov - 9 Nov
4 Mi to Beach & Dtwn! Charming Fairfield Home

9. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.4 out of 10, Exceptional, (19 reviews)
"The accommodations were incredible. The host provided many helpful materials that made the stay very comfortable. The apartment was very cute and had nice amenities for the guests that go above any beyond what a hotel can provide."
United States
Bailey
The price is NZ$391
includes taxes & fees
6 Nov - 7 Nov
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

10. Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is NZ$430
includes taxes & fees
9 Nov - 10 Nov
Spacious Studio with Pool Table

11. Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
8.0 out of 10, Very good, (7 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is NZ$570
includes taxes & fees
8 Nov - 9 Nov
Modern 2 Bed in BlackRock

12. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (29 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is NZ$708
includes taxes & fees
9 Nov - 10 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.

13. Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (60 reviews)
"Definitely clean - good place for an overnight stay."
United States
Kimberly
The price is NZ$257
includes taxes & fees
11 Nov - 12 Nov
Business or Weekend escape

14. Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (3 reviews)
"We had an awesome time staying Here Everything was super clean And the communication with the host was great we would greatly recommend would definitely stay again!"
United States
Anonymous traveller
The price is NZ$525
includes taxes & fees
30 Nov - 1 Dec
Renovated 2BR Retreat / Modern Comforts Included

15. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$664
includes taxes & fees
9 Nov - 10 Nov
Guesthouse at Norwalk Inn

16. Centric property close to all the great things in the city

Centric property close to all the great things in the city
Brooklawn - St. Vincent
6.8 out of 10, (18 reviews)
"This rental was great accommodation"
United States
Alma B.
The price is NZ$449
includes taxes & fees
18 Nov - 19 Nov
Centric property close to all the great things in the city

17. Elite room stay

Elite room stay
Bridgeport
The price is NZ$582
includes taxes & fees
6 Nov - 7 Nov
Elite room stay

18. The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry
Brooklawn - St. Vincent
The price is NZ$608
includes taxes & fees
9 Nov - 10 Nov
The B&W Haven: Stylish 3BR Escape with Private Office by LI Ferry

19. Cozy 2-Bed ADA|Pool|Free Parking

Cozy 2-Bed ADA|Pool|Free Parking
MILFORD
10.0 out of 10, Exceptional, (4 reviews)
"Would tell anyone passing through to stop here if they want quick check-in and restful sleep quality. Parking is easy to find close by, so no hassle with unloading bags."
United States
Anonymous traveller
The price is NZ$140
includes taxes & fees
22 Nov - 23 Nov
Cozy 2-Bed ADA|Pool|Free Parking

20. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.4 out of 10, Exceptional, (19 reviews)
"A sweet get away for which the highlights included a breezy screened porch and sensational walks right from the property. Easy shopping and neighbors right out of central casting who provided additional restaurant suggestions and general warmth. Would stay here again in a heart beat. We were here for a week and were sad to leave."
United States
Mel O.
The price is NZ$952
includes taxes & fees
11 Nov - 12 Nov
Nama-stay, sweet pink Saugatuck Shores beach cottage
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fairfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fairfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fairfield. Seeing all the best attractions is bound to make you fall in love with Fairfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fairfield short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Fairfield?

Yes, there are holiday rentals in Fairfield close to Fairfield Theater Company, 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?

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends: This holiday home rental outside of Fairfield is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 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 48 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 Connecticut Audubon Birdcraft Museum. 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.