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Find Curated Vacation Rentals, Boutique Cabins, and Stylish Eco-Friendly Acommodation in Fairfield

Downtown, Luxury Rock‘n Roll/Bourbon vibe, Historic Home, indoor sauna, 3 kings in Bardstown From US $931
         

10.0 (32 Reviews)
House
Downtown, Luxury Rock‘n Roll/Bourbon vibe, Historic Home, indoor sauna, 3 kings
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Luxury Places to Stay in Fairfield

Over 260+ Luxury Places to Stay in or Near Fairfield
New 10 BR Luxury | Sleeps 20 | Bourbon Country in Bardstown From US $3,004
         

New
House
New 10 BR Luxury | Sleeps 20 | Bourbon Country
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Luxury in the Country. Chalet Style Cabin on secluded 61 Acres with 3 acre Lake in Bloomfield From US $1,651
         

10.0 (1 Review)
Cabin
Luxury in the Country. Chalet Style Cabin on secluded 61 Acres with 3 acre Lake
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bourbon Trail Cabin + Huge Game Room + Hot Tub in Bloomfield From US $1,120
         

10.0 (29 Reviews)
Cabin
Bourbon Trail Cabin + Huge Game Room + Hot Tub
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  • Pool

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Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub in Bloomfield From US $987
         

10.0 (10 Reviews)
House
Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bourbon Trail Estate on 22.5 Acres! in Coxs Creek From US $934
         

9.6 (25 Reviews)
House
Bourbon Trail Estate on 22.5 Acres!
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DERBY SPECIAL includes parking spot 50 ft from the track . 6-bedroom lodge in Bloomfield From US $890
         

New
Cabin
DERBY SPECIAL includes parking spot 50 ft from the track . 6-bedroom lodge
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BOURBON TRAIL: Bardstown 3 bedroom/3 bath cottage, park setting, walk to downtown in Bardstown From US $865
         

New
Bed & Breakfast
BOURBON TRAIL: Bardstown 3 bedroom/3 bath cottage, park setting, walk to downtown
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The Full Proof Penthouse in Downtown Bardstown - Walking to Restaurants & Shops! in Bardstown From US $853
         

New
Apartment
The Full Proof Penthouse in Downtown Bardstown - Walking to Restaurants & Shops!
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Top-Rated Vacation Rentals with a Pool in Fairfield

Over 77+ Top-Rated Vacation Rentals with a Pool in or Near Fairfield
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail in Taylorsville From US $213
         

10.0 (244 Reviews)
Cottage
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
  • Air Conditioner
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  • Pool

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Luxurious Suite w/Garden on Court Square Downtown in Bardstown From US $217
         

10.0 (138 Reviews)
Hotel
Luxurious Suite w/Garden on Court Square Downtown
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1-bedroom poolhouse w/private heated pool, within 10 miles to 11 distilleries. in Bloomfield From US $299
         

10.0 (26 Reviews)
House
1-bedroom poolhouse w/private heated pool, within 10 miles to 11 distilleries.
  • Air Conditioner
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  • Pool

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Boating, bourbon and high speed internet, oh my! in Taylorsville From US $227
         

10.0 (18 Reviews)
Cottage
Boating, bourbon and high speed internet, oh my!
  • Air Conditioner
  • Parking
  • Pool

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Whiskey River Cottage - Located on Ky Bourbon Trail and Taylorsville Lake in Taylorsville From US $243
         

10.0 (13 Reviews)
Cottage
Whiskey River Cottage - Located on Ky Bourbon Trail and Taylorsville Lake
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  • Pet Friendly

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Taylorsville Tranquil Retreat: 2BD/2BA with Hot Tub, Lake Access, Bourbon Trail in Taylorsville From US $275
         

10.0 (5 Reviews)
Cottage
Taylorsville Tranquil Retreat: 2BD/2BA with Hot Tub, Lake Access, Bourbon Trail
  • Air Conditioner
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  • Pet Friendly

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Ryes & Shine-Cottage 77 Hot Tub+Lake+Bourbon Trail in Taylorsville From US $300
         

10.0 (2 Reviews)
Cottage
Ryes & Shine-Cottage 77 Hot Tub+Lake+Bourbon Trail
  • Air Conditioner
  • Parking
  • Pool

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40- Lake and Bourbon Trail Getaway in Taylorsville From US $206
         

10.0 (2 Reviews)
House
40- Lake and Bourbon Trail Getaway
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  • Pool

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Pet-Friendly Vacation Rentals in Fairfield

Over 64+ Pet-Friendly Vacation Rentals in or Near Fairfield
Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool in Taylorsville From US $244
         

9.6 (55 Reviews)
House
Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hot Tub Sleeps 10 Bourbon Trail Historic Home in Coxs Creek From US $225
         

10.0 (3 Reviews)
House
Hot Tub Sleeps 10 Bourbon Trail Historic Home
  • Air Conditioner
  • Parking
  • Pet Friendly

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La Quinta Inn & Suites by Wyndham Bardstown in Bardstown From US $123
         

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9.2 (1124 Reviews)
Hotel
La Quinta Inn & Suites by Wyndham Bardstown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Best View of Taylorville Lake My Perfect Place in Taylorsville From US $230
         

9.4 (77 Reviews)
Cottage
Best View of Taylorville Lake My Perfect Place
  • Air Conditioner
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  • Pet Friendly

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Bourbon Belle of Bardstown - Walk to Downtown & Ready for the Bourbon Trail! in Bardstown From US $331
         

10.0 (56 Reviews)
House
Bourbon Belle of Bardstown - Walk to Downtown & Ready for the Bourbon Trail!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern rustic home near Bardstown top distilleries in Bardstown From US $313
         

10.0 (31 Reviews)
House
Modern rustic home near Bardstown top distilleries
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Hot Tub- Sleeps 10- Bourbon Trail- Historic Home in Coxs Creek From US $318
         

10.0 (23 Reviews)
House
Hot Tub- Sleeps 10- Bourbon Trail- Historic Home
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  • Pet Friendly

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Welcome to Bourbon Oak Smokehouse, in the heart of Bardstown, KY in Bardstown From US $306
         

10.0 (18 Reviews)
Cottage
Welcome to Bourbon Oak Smokehouse, in the heart of Bardstown, KY
  • Air Conditioner
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  • Pet Friendly

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Large Vacation Homes & Villas in Fairfield

Over 35+ Large Vacation Homes & Villas in or Near Fairfield
"On the Rocks" Bourbon Trail Getaway in Taylorsville From US $585
         

9.0 (45 Reviews)
Cottage
"On the Rocks" Bourbon Trail Getaway
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22-Acre Home on Bourbon Trail w/Sunroom! in Coxs Creek From US $418
         

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10.0 (2 Reviews)
House
22-Acre Home on Bourbon Trail w/Sunroom!
  • Parking
  • Pet Friendly
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Luxury Retreat: Golf Sim, Massage Chairs, Curved Cinema in Bardstown From US $849
         

10.0 (5 Reviews)
House
Luxury Retreat: Golf Sim, Massage Chairs, Curved Cinema
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  • Pool

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Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown! in Bardstown From US $536
         

10.0 (35 Reviews)
House
Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!
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Luxurious 5-Bed Escape in Heart of Bourbon Trail in Bloomfield From US $696
         

10.0 (23 Reviews)
House
Luxurious 5-Bed Escape in Heart of Bourbon Trail
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NEW Hot Tub 5BR Estate Near Bourbon Trail w/history in Bardstown From US $454
         

10.0 (22 Reviews)
House
NEW Hot Tub 5BR Estate Near Bourbon Trail w/history
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The Lodge/Hot Tub, Arcade, Firepit, Game room! in Coxs Creek From US $642
         

10.0 (17 Reviews)
Cabin
The Lodge/Hot Tub, Arcade, Firepit, Game room!
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Luxury 5 Acre Bourbon Estate with Private Pond, Theater and Game Room in Bardstown From US $700
         

10.0 (6 Reviews)
House
Luxury 5 Acre Bourbon Estate with Private Pond, Theater and Game Room
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Wheelchair Accessible Vacation Homes in Fairfield

Over 13+ Wheelchair Accessible Vacation Homes in or Near Fairfield
Talbott Tavern and Inn in Bardstown From US $196
         

9.0 (491 Reviews)
Bed & Breakfast
Talbott Tavern and Inn
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Distill-Inn in Bardstown From US $107
         

9.4 (1579 Reviews)
Hotel
Distill-Inn
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Americas Inn Bardstown in Bardstown From US $90
         

7.9 (171 Reviews)
Hotel
Americas Inn Bardstown
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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Fairfield Inn & Suites by Marriott Bardstown in Bardstown From US $203
         

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9.2 (484 Reviews)
Hotel
Fairfield Inn & Suites by Marriott Bardstown
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La Quinta Inn & Suites by Wyndham Bardstown in Bardstown From US $179
         

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9.1 (623 Reviews)
Hotel
La Quinta Inn & Suites by Wyndham Bardstown
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Trail Hotel in Bardstown From US $162
         

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9.2 (317 Reviews)
Hotel
The Trail Hotel
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  • Parking
  • Pool

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Bardstown Motor Lodge in Bardstown From US $189
         

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8.7 (128 Reviews)
Hotel
Bardstown Motor Lodge
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  • Pet Friendly

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Holiday Inn Express & Suites Bardstown by IHG in Bardstown From US $112
         

8.4 (539 Reviews)
Hotel
Holiday Inn Express & Suites Bardstown by IHG
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Fairfield Vacation Rentals and Airbnb Places to Stay Under $200

Over 36+ Fairfield Vacation Rentals and Airbnb Places to Stay Under $200
A Room Off Broadway, a prime downtown hideaway in Bardstown From US $172
         

10.0 (133 Reviews)
Apartment
A Room Off Broadway, a prime downtown hideaway
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3BR Home Near Louisville | King Suite Fenced Yard in Mount Washington From US $150
         

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10.0 (1 Review)
House
3BR Home Near Louisville | King Suite Fenced Yard
  • Parking
  • Pet Friendly
  • View

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Jailer's Inn in Bardstown From US $176
         

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9.4 (219 Reviews)
Bed & Breakfast
Jailer's Inn
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Historic Loft in the ❤️ of Bardstown in Bardstown From US $197
         

10.0 (32 Reviews)
Apartment
Historic Loft in the ❤️ of Bardstown
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Charming 1-bedroom house in enjoyable Bardstown with AC, WiFi in Bardstown From US $179
         

10.0 (2 Reviews)
House
Charming 1-bedroom house in enjoyable Bardstown with AC, WiFi
  • Air Conditioner
  • Security/Safety
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Stay in a historic Early 1800s Guest House! in Bardstown From US $189
         

9.8 (135 Reviews)
House
Stay in a historic Early 1800s Guest House!
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Bourbon Country Cottage - perfect for exploring the Bourbon Trail in Bardstown From US $167
         

9.6 (20 Reviews)
Cottage
Bourbon Country Cottage - perfect for exploring the Bourbon Trail
  • Air Conditioner
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Belle Beam Room-easy walk to downtown & 10mins to distilleries in Bardstown From US $146
         

9.8 (9 Reviews)
Apartment
Belle Beam Room-easy walk to downtown & 10mins to distilleries
  • Air Conditioner
  • Parking
  • Pet Friendly

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Instantly Bookable Vacation Homes in Fairfield

Over 129+ Instantly Bookable Vacation Homes in or Near Fairfield
1 STORY 3 Bd 2 Ba/4 Beds 3XLong FULLY STOCKED on Bourbon Trail GARAGE Patio BBQ in Bardstown From US $326
         

10.0 (94 Reviews)
House
1 STORY 3 Bd 2 Ba/4 Beds 3XLong FULLY STOCKED on Bourbon Trail GARAGE Patio BBQ
  • Air Conditioner
  • Parking
  • TV

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One of a kind cabin in the woods. Quiet and private but close to everything. in Coxs Creek From US $216
         

10.0 (128 Reviews)
Cottage
One of a kind cabin in the woods. Quiet and private but close to everything.
  • Air Conditioner
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Secluded 2 Bedroom Sanctuary on 20 Acres in the Heart of the Bourbon Trail in Chaplin From US $285
         

10.0 (87 Reviews)
Cabin
Secluded 2 Bedroom Sanctuary on 20 Acres in the Heart of the Bourbon Trail
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Historic Bardstown Cottage in Bardstown From US $241
         

10.0 (73 Reviews)
House
Historic Bardstown Cottage
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Golf View Sunset Porch-Sittin' 4 bed, Basement Bar/GameRoom, Free Coffee in Bardstown From US $584
         

10.0 (70 Reviews)
House
Golf View Sunset Porch-Sittin' 4 bed, Basement Bar/GameRoom, Free Coffee
  • Air Conditioner
  • Parking
  • TV

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Bourbon on Broadway- 3 King Bed- Downtown Bardstown-Walk everywhere! in Bardstown From US $443
         

10.0 (69 Reviews)
House
Bourbon on Broadway- 3 King Bed- Downtown Bardstown-Walk everywhere!
  • Air Conditioner
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  • TV

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🌾 The Farmwife’s Hideaway 🌾 Small-town comfort with farmhouse charm. in Bardstown From US $289
         

10.0 (65 Reviews)
House
🌾 The Farmwife’s Hideaway 🌾 Small-town comfort with farmhouse charm.
  • Air Conditioner
  • Parking
  • TV

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Bluegrass & Bourbon - a Peaceful Retreat & Hangout in Bardstown From US $391
         

10.0 (62 Reviews)
House
Bluegrass & Bourbon - a Peaceful Retreat & Hangout
  • Air Conditioner
  • Parking
  • TV

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About Fairfield Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bettertrips Fairfield, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Fairfield. Places to stay near Fairfield are 3000 ft² on average, with prices averaging US $931 a night.

Bettertrips makes it easy and safe to find and compare vacation rentals in Fairfield with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Fairfield

Type Count
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Fairfield

★ Pro Tip: Bettertrips makes it easy to compare the best listings on Bettertrips homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bettertrips homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Fairfield.

Weather in Fairfield

View the weather forecast for Fairfield before booking your Fairfield Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Fairfield, KY

Bettertrips offers a large selection of top attractions around Fairfield. Research things to do on your vacation before you visit Fairfield.


Barton 1792 Distillery Jim Beam American Outpost Taylorsville Lake State Park Paroquet Springs Conference Center Heaven Hill Bourbon Heritage Center Taylorsville Lake My Old Kentucky Home State Park Bernheim Arboretum and Research Forest Bourbon Heritage Center Bardstown Civil War Museum Talon Winery Wickland Awesome Flea Market Shaq & Coco Forest Edge Winery Cedar-Fil Golf Course Sanctuary Arts Center Brashears Creek The Red Scooter Bardstown Art Gallery

Fairfield Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Fairfield?

Currently, the total number of properties listed in 2026 is over 1 in the Fairfield area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Fairfield.