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Top Holiday Rentals in Springfield

Unique Cabin on the Beechfork River, nestled in the heart of the Bourbon Trail

2.0 star property
10.0 out of 10, Exceptional, (25)
"Perfect place for our small family. Private, clean and unique. "
Unique Cabin on the Beechfork River, nestled in the heart of the Bourbon Trail

“Bourbon, Bands & Big Summer Savings — Sip, Sing & Save!”

10.0 out of 10, Exceptional, (25)
"Highly recommended this is the perfect place to get away and relax "
The price is £303
includes taxes & fees
30 Jun - 1 Jul
“Bourbon, Bands & Big Summer Savings — Sip, Sing & Save!”

Historic Simmstown Manor Located on Bourbon Trail

10.0 out of 10, Exceptional, (38)
"We LOVED the house and property. It was exactly the retreat we needed during a difficult time. The owner was lovely to visit with and the horses were beautiful. We will be staying here again. "
Historic Simmstown Manor Located on Bourbon Trail

Bourbon Trail Oasis at Boone Farm - Private & Peaceful

2.0 star property
10.0 out of 10, Exceptional, (4)
"Really enjoyed our visit, which met our needs very well."
The price is £199
includes taxes & fees
16 Jun - 17 Jun
Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Country Cottage on the Bourbon Trail, near Bardstown, Peaceful, Family, Couples

10.0 out of 10, Exceptional, (7)
"Fantastic location and super comfortable place. Can’t say enough about the accommodations, will absolutely book again!"
Country Cottage on the Bourbon Trail, near Bardstown, Peaceful, Family, Couples

Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!

10.0 out of 10, Exceptional, (6)
The price is £190
includes taxes & fees
22 Jun - 23 Jun
Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!

Cozy cottage in charming New Hope with AC, WiFi

9.4 out of 10, Exceptional, (3)
"Perfect little cottage to unwind in after a day on the road. Clean and the bed is super comfy. Situated close to the Bourbon Trail distilleries. Our hosts (Jon and Robin) really paid attention to details from the bottled water in the frig to the coffee pods for the Keurig. We will definitely stay again when we're in the area."
The price is £139
includes taxes & fees
16 Jun - 17 Jun
Cozy cottage in charming New Hope with AC, WiFi

Spacious, Fully-Stocked, Walking distance to Downtown

10.0 out of 10, Exceptional, (19)
"The house was very home like and accommodating. We definitely enjoyed our stay even tho it rained the whole time! "
Spacious, Fully-Stocked, Walking distance to Downtown

KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

9.8 out of 10, Exceptional, (116)
"Our stay didn’t go as planned as it rained, snowed and was cold the whole time. However the home was very nice and the little touches, like a basket a snacks, stocked bathroom supplies made the stay very enjoyable.The owners go above and beyond to make it feel homey unlike most rentals we have used."
KY BOURBON TRAIL LAKEFRONT HOUSE WITH DOCK SLEEPS 8! Year round Hot tub!

High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20

10.0 out of 10, Exceptional, (1)
"This property is tucked away in secluded rolling hills just west of Lexington. It is a perfect location for Keeneland activities! (only 12 minutes away)Every detail has been thought through at this lovely home! The decor is tastefully done and reflects the horse and bourbon culture beautifully. There is plenty of room inside and out for family to gather, share conversation, and play. There are more than enough bathrooms, towels and pool towels as well! The pool house provides a great space to...
The price is £1,222
includes taxes & fees
29 Jun - 30 Jun
High Spirits Estate - Pool, Hot Tub, Game Room, EV charger, Sleeps 20

It's rare to find a place that's both historic & one-of-a-kind

10.0 out of 10, Exceptional, (37)
"Beautiful and perfect place to stay. "
The price is £119
includes taxes & fees
24 Jun - 25 Jun
It's rare to find a place that's both historic & one-of-a-kind

The Farmwife’s Hideaway

10.0 out of 10, Exceptional, (17)
"A peaceful comfortable place near the Bardstown Bourbon trail favorites. I highly recommend this place for your stay."
The price is £237
includes taxes & fees
17 Jun - 18 Jun
The Farmwife’s Hideaway

Bluegrass & Bourbon - a Peaceful Retreat & Hangout

10.0 out of 10, Exceptional, (27)
"Great property right in heart of bardstown. Great location for our group as we did a couple of barrel picks this week. Will absolutely stay here again!"
The price is £255
includes taxes & fees
24 Jun - 25 Jun
Bluegrass & Bourbon - a Peaceful Retreat & Hangout

Downtown Danville Luxury House, walk to restaurants & bars, dog friendly

9.2 out of 10, Wonderful, (12)
"Clean and conveniently located in Danville. I loved the space and it was so close to my family I was visiting !!!!!! "
The price is £203
includes taxes & fees
16 Jun - 17 Jun
Downtown Danville Luxury House, walk to restaurants & bars, dog friendly

Beautiful apartment in the heart of downtown Bardstown, KY

9.6 out of 10, Exceptional, (135)
"We loved the location and the quaintness of the property. It would be difficult to access if you have any problems with stairs."
The price is £168
includes taxes & fees
29 Jun - 30 Jun
Beautiful apartment in the heart of downtown Bardstown, KY

Lakefront Home Close to Bourbon Trail--Dog friendly!

9.8 out of 10, Exceptional, (73)
"Wonderful place. "
Lakefront Home Close to Bourbon Trail--Dog friendly!

Apartment Downtown Bardstown<br>The PACK

10.0 out of 10, Exceptional, (53)
"Such a beautifully decorated and easy location in Bardstown. We enjoyed our stay very much. "
The price is £185
includes taxes & fees
16 Jun - 17 Jun
Apartment Downtown Bardstown<br>The PACK

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

9.6 out of 10, Exceptional, (71)
"This place is just adorable and perfect location! "
The price is £163
includes taxes & fees
23 Jun - 24 Jun
Stay downtown within walking distance of restaurants, shopping, and breweries!

NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

The price is £550
includes taxes & fees
17 Jun - 18 Jun
NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi

10.0 out of 10, Exceptional, (48)
"The property is amazing. The views. The privacy. Love the setting and the decor. The fire places were great. Very comfortable. We will be back. "
Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi
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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Frequently asked questions

Can I find holiday rentals in Springfield?

Yes, there are holiday rentals close to the most popular sights in Springfield, or you can select a more secluded option if you're looking for a relaxing stay. Springfield is known for its coffee shops and parks. Make sure you have time to check out the museums while you're in the area.

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

Bourbon Trail Oasis at Boone Farm - Private & Peaceful: This highly rated holiday home rental in Springfield offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable 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 will I find in Springfield?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Springfield stay.

What’s there to see and do in Springfield?

Explore the area and family-friendly sights such as Shaq & Coco, or get out into nature at a spot like Perryville Battlefield State Historic Site. Other places in town to visit include Lincoln Legacy Museum and Lincoln Homestead State Park.

What’s a holiday rental in Springfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Springfield. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family gatherings.