Fairfield Holiday Rentals

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Holiday Rentals in Fairfield

Stay downtown within walking distance of restaurants, shopping, and breweries!

9.6 out of 10, Exceptional, (56)
"So easy to check in and it was centrally located near shops and bars! Place was clean and so well kept! Will come back for sure "
The price is AU$337
includes taxes & fees
27 Nov - 28 Nov
Stay downtown within walking distance of restaurants, shopping, and breweries!

Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

10.0 out of 10, Exceptional, (197)
"I am a 65 YO woman and I stayed at this cottage by myself the week of 10/22/24. I am pleased to give a 5-star rating because: this cottage was easy to find and located in a pleasant, quiet area. I felt safe in this cottage; it was very clean; bed slept wonderful; water pressure and temp were great; cottage looks exactly like pictures; everything worked as expected, and my communications with the property manager were easy. This area is wonderful if you want peace and quiet, close to the lake...
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

Stay in a historic Early 1800s Guest House!

10.0 out of 10, Exceptional, (88)
"Very cute Guest House. 1 block from Main St. close to restaurants and bars. Clean, great wifi, tv and comfi bed. Owners are responsive and there if you need them. Price was great. Would rent again."
The price is AU$300
includes taxes & fees
2 Dec - 3 Dec
Stay in a historic Early 1800s Guest House!

22-acre Home on Bourbon Trail w/ Sunroom!

3.0 star property
22-acre Home on Bourbon Trail w/ Sunroom!

Captain's Cabin Bed & Breakfast: Historic & Romantic

9.8 out of 10, Exceptional, (127)
"Had a great weekend at Captain's cabin. we immediately started a fire in the fireplace and enjoyed the quiet popping and warmth of the fire all weekend. Tammy's breakfasts are outstanding. Found some fun things to do in town when we finally pealed ourselves from the cabin."
The price is AU$645
includes taxes & fees
1 Dec - 2 Dec
Captain's Cabin Bed & Breakfast: Historic & Romantic

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

9.8 out of 10, Exceptional, (78)
"The host of this property is great. She communicates well and was easily accessible. The property is clean and in a great location if you are looking for things south of Louisville. Great layout for families with kids and in-laws. "
The price is AU$689
includes taxes & fees
2 Dec - 3 Dec
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Luxurious 2BR /2Bath with Outdoor Courtyard and Garage in Downtown Bardstown

10.0 out of 10, Exceptional, (210)
"Lovely house in the heart of bourbon country. Plenty of places within walking distance to eat. Short drive to many distilleries. Highly recommend!"
The price is AU$707
includes taxes & fees
1 Dec - 2 Dec
Luxurious 2BR /2Bath with Outdoor Courtyard and Garage in Downtown Bardstown

Beautiful apartment in the heart of downtown Bardstown, KY

9.8 out of 10, Exceptional, (120)
"It’s a nice little apartment right in the mixdle"
The price is AU$353
includes taxes & fees
1 Dec - 2 Dec
Beautiful apartment in the heart of downtown Bardstown, KY

Angels Envy 29 - A relaxing place by the lake!

9.6 out of 10, Exceptional, (14)
"Great place good accommodation "
The price is AU$467
includes taxes & fees
24 Nov - 25 Nov
Angels Envy 29 - A relaxing place by the lake!

Ron & Orline's Home, park at the door & use our EV 50 amp charger

10.0 out of 10, Exceptional, (147)
"Great property and great location. "
The price is AU$403
includes taxes & fees
29 Nov - 30 Nov
Ron & Orline's Home, park at the door & use our EV 50 amp charger

A Romantic Getaway on the Bourbon Trail

10.0 out of 10, Exceptional, (38)
"The accommodation is well equipped and extremely clean. The property is beautiful and lends itself to a relaxing getaway. To top it all off the hosts were very welcoming and communicative. If you are looking for an idyllic place to stay in the area, you've found the right listing."
A Romantic Getaway on the Bourbon Trail

GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake

9.2 out of 10, Wonderful, (29)
"Property was clean, easy access. Beautiful area. We were there for the weekend of our daughters wedding in Shelbyville. "
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake

Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks

10.0 out of 10, Exceptional, (9)
"Conveniently located and very relaxing"
Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks

All You Need and More!

9.6 out of 10, Exceptional, (112)
"My friends and I booked this property so that we would have accommodations for all of us. The property was clean and spacious. The owner was very communicative. The stay was very smooth overall. Although we were a group of five adults, this property would be ideal for a family or families. Be aware that the property is about a 25 minute Uber ride from Main Street (and the listing does not suggest otherwise). Our group was happy to sacrifice proximity to Main Street in order to have...
All You Need and More!

Historically Registered 1847 log Cabin

10.0 out of 10, Exceptional, (137)
"Clean, organized, fully stocked, great for kids, in a beautiful neighborhood."
Historically Registered 1847 log Cabin

Bardstown Kentucky , large space

10.0 out of 10, Exceptional, (97)
"This is a perfect spot to stay to check out the bourbon trail "
Bardstown Kentucky , large space

Bourbon Trail Estate on 22.5 Acres!

10.0 out of 10, Exceptional, (12)
"Had 4 couples stay for a bourbon trip. The house exceeded our expectations. "
Bourbon Trail Estate on 22.5 Acres!

A-Framed View in Kentucky

10.0 out of 10, Exceptional, (26)
"My wife loved the decor it was perfect but not to muuch. Clean tidy and cute overall and good communication. Highly recommend getting up to watch the sunrise! We had clear skies and each morning some fog settled in over the back fields before sunrise, excellant way to start the day!"
The price is AU$753
includes taxes & fees
9 Dec - 10 Dec
A-Framed View in Kentucky

Secluded 2 Bedroom Sanctuary on 20 Acres in the Heart of the Bourbon Trail

10.0 out of 10, Exceptional, (50)
"We truly loved our stay. It was just the perfect setting, and it was so close to everything. It was comfortable and inviting and felt like home away from home. We would recommend this place to anyone who visits Kentucky. We will definitely be back :)"
Secluded 2 Bedroom Sanctuary on 20 Acres in the Heart of the Bourbon Trail

The Angels Share 4BR 1 BATH in Bardstown KY

10.0 out of 10, Exceptional, (16)
"Dad and adult sons had a great stay. The house had everything we needed and we enjoyed the fire pit outside overlooking the 1792 distillery. Walking distance to downtown allowed for a dinner without concern for a DD. "
The price is AU$466
includes taxes & fees
8 Dec - 9 Dec
The Angels Share 4BR 1 BATH in Bardstown KY
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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Other types of properties in Fairfield you may be interested in

Distill-Inn

2.5 star property
9.2 out of 10, Wonderful, (928)
"Our room was clean and the bed was very comfortable. The bar was nice but definitely needed some upbeat music, kinda boring 😴. The breakfast was good and offered a different selection of food "
The price is AU$195
includes taxes & fees
6 Dec - 7 Dec
Distill-Inn

La Quinta Inn & Suites by Wyndham Bardstown

2.5 star property
9.0 out of 10, Wonderful, (719)
"Great stay "
The price is AU$166
includes taxes & fees
23 Dec - 24 Dec
La Quinta Inn & Suites by Wyndham Bardstown

Best Western Louisville South / Shepherdsville

2.5 star property
8.6 out of 10, Excellent, (645)
"The place is older but the rooms were clean. Bedsheets were as advertised and breakfast was awesome!"
The price is AU$129
includes taxes & fees
24 Dec - 25 Dec
Best Western Louisville South / Shepherdsville
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Fairfield?

Yes, there are holiday rentals close to the most popular sights in Fairfield, or you can select a more secluded option if you're looking for a relaxing stay.

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

Stay in a historic Early 1800s Guest House!: This holiday home rental outside of Fairfield is in the city centre, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Fairfield?

Explore the area and family-friendly sights such as The Red Scooter, or get out into nature at a spot like Taylorsville Lake. Lux Row Distillers and Bardstown Civil War Museum are a couple of places you'll find in the wider area.

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 provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for small groups.