Orlando Vacation Rentals - Vacation Rentals in Fairfield

22-Acre Home on Bourbon Trail with Sunroom! From US $552
         

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10.0 (2 Reviews)
House
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  • Pet Friendly
  • Accessibility
Red Rose Inn Bed & Breakfast From US $290
         

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10.0 (56 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
"On the Rocks" Bourbon Trail Getaway From US $495
         

9.0 (42 Reviews)
Cottage
  • Air Conditioner
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Best View of Taylorville Lake My Perfect Place From US $177
         

9.4 (70 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Fairfield

Over 215+ Luxury Places to Stay in or Near Fairfield
LogCabin-15 min Bardstown Pool From US $841
         

10.0 (24 Reviews)
Cabin
  • Air Conditioner
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  • Pool
Bourbon Trail Estate on 22.5 Acres! From US $807
         

10.0 (23 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Bluegrass Grand Estate: Bourbon Trail Luxury From US $737
         

9.4 (3 Reviews)
House
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  • Parking
  • Pool
Bourbon Trail Cabin - Central to the Distilleries From US $674
         

9.6 (9 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Fairfield

Over 64+ Top-Rated Vacation Rentals with a Pool in or Near Fairfield
Cozy KY Escape with Hot Tub near the Bourbon Trail From US $280
         

Boating, bourbon and high speed internet, oh my! From US $191
         

10.0 (16 Reviews)
Cottage
  • Air Conditioner
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  • Pool
55- Lake & Bourbon Trail Getaway From US $164
         

10.0 (3 Reviews)
Cottage
  • Air Conditioner
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  • Pool
40- Lake and Bourbon Trail Getaway From US $206
         

10.0 (2 Reviews)
House
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  • Parking
  • Pool
Kentucky Sunrise 18- Greet the Sun As it Rises From US $310
         

9.8 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Fairfield

Over 39+ Pet-Friendly Vacation Rentals in or Near Fairfield
Central Bardstown Home Near Distilleries & Dining From US $370
         

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10.0 (1 Review)
House
  • Air Conditioner
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  • Pet Friendly
La Quinta Inn & Suites by Wyndham Bardstown From US $102
         

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9.2 (1016 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
22-Acre Home on Bourbon Trail w/Sunroom! From US $375
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious & Stylish Central Bardstown Home! From US $307
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Whiskey River Cottage - Located on Ky Bourbon Trail and Taylorsville Lake From US $162
         

Welcome to Bourbon Oak Smokehouse, in the heart of Bardstown, KY From US $305
         

Large Vacation Homes & Villas in Fairfield

Over 16+ Large Vacation Homes & Villas in or Near Fairfield
Talbott Tavern and Inn From US $139
         

8.9 (518 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Luxurious 5-Bed Escape in Heart of Bourbon Trail From US $660
         

Bardstown & Bourbon Lodge/Hot Tubbing & BBQing From US $630
         

3B/3B; Single Family Lakeside Retreat W/Hot Tub From US $231
         

9.6 (59 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Kentucky Derby Guest House < 16 guest ! From US $136
         

9.0 (47 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Bardstown w/Hot Tub & Poker Table From US $375
         

9.8 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Fairfield

Over 13+ Wheelchair Accessible Vacation Homes in or Near Fairfield
Americas Inn Bardstown From US $90
         

7.9 (171 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Distill-Inn From US $109
         

9.2 (1400 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Distill-Inn From US $129
         

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9.0 (518 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Fairfield Inn & Suites by Marriott Bardstown From US $102
         

9.2 (439 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
La Quinta Inn & Suites by Wyndham Bardstown From US $111
         

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8.8 (645 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Trail Hotel From US $196
         

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8.8 (105 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Bardstown Motor Lodge From US $382
         

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8.4 (91 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday Inn Express & Suites Bardstown by IHG From US $87
         

8.6 (476 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Fairfield Varoom and Airbnb Places to Stay Under $200

Over 51+ Fairfield Varoom and Airbnb Places to Stay Under $200
Haven Hill House - Scenic Getaway near Bardstown & Bourbon Trail From US $135
         

9.7 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Bourbon Manor B&B From US $197
         

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9.8 (76 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
A Room Off Broadway, a prime downtown hideaway From US $149
         

10.0 (109 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Historic Bardstown Cottage From US $161
         

10.0 (61 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Historic Loft in the ❤️ of Bardstown From US $130
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
The Hideout on 3rd in Historic Downtown Bardstown on Main St From US $143
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Fairfield

Over 101+ Instantly Bookable Vacation Homes in or Near Fairfield
Bluegrass & Bourbon - a Peaceful Retreat & Hangout From US $348
         

Quiet escape in the middle of town! From US $313
         

10.0 (40 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming 4BR w/Fire Pit + Next to Barton 1792 From US $313
         

About Fairfield Vacation Rentals

With more than 224 Fairfield vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Orlando Vacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Fairfield.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Orlando Vacationrentals 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 883.48 ft² on average, with prices averaging $306 a night.

Orlando Vacationrentals 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 111
Cottages 37
Holiday Apartments 25
Hotels with Suites 24
Cabin Rentals 15
B&B 7
Others 5

Use these Quick Filters to Find a Vacation Rental in Fairfield

Pro Tip: Orlando Vacationrentals makes it easy to compare the best listings on Orlando Vacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Orlando Vacationrentals 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