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Compare 156 Vacation Homes in Boston with updated reviews, rates, and availability.

The Farmwife’s Hideaway

10.0 out of 10, Exceptional, (11)
"Great place to stay with plenty to do."
The price is AED 760
AED 1,255 total
includes taxes & fees
29 Apr - 30 Apr
The Farmwife’s Hideaway

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

10.0 out of 10, Exceptional, (89)
"Nice, comfy home. The property was clean and convenient. Tammy was easy to contact and very helpful. Definitely would book again."
The price is AED 1,466
AED 2,764 total
includes taxes & fees
27 Apr - 28 Apr
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

Just 10 minutes from town -We're more than just a place to stay!

10.0 out of 10, Exceptional, (3)
"It was so great. Super clean and awesome location. We got to roam around and enjoy the property as well"
Just 10 minutes from town -We're more than just a place to stay!

Bourbon Trail Estate on 22.5 Acres!

10.0 out of 10, Exceptional, (16)
"Had 4 couples stay for a bourbon trip. The house exceeded our expectations. "
Bourbon Trail Estate on 22.5 Acres!

"Parkside Haven with Hot Tub Near Bourbon Trail & Louisville"

10.0 out of 10, Exceptional, (20)
"Wonderful place that was exactly what we needed while in the area, the hot tub was awesome"
"Parkside Haven with Hot Tub Near Bourbon Trail & Louisville"

Comfy home in military community

8.0 out of 10, Very Good, (5)
"We stay in Louisville, Kentucky twice a month starting in September until December and this home is a little outside of Louisville but still was the best home we have stayed in within the last two baseball fall seasons. It was worth the little extra drive from the baseball fields to have a comfortable home to stay in. "
Comfy home in military community

Stay in a historic Early 1800s Guest House!

10.0 out of 10, Exceptional, (95)
"Loved this little cottage in Bardstown. Clean, lots of room and great location. Would definitely stay again. "
The price is AED 422
AED 705 total
includes taxes & fees
28 Apr - 29 Apr
Stay in a historic Early 1800s Guest House!

Bluegrass & Bourbon - a Peaceful Retreat & Hangout

10.0 out of 10, Exceptional, (26)
"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 AED 419
AED 1,263 total
includes taxes & fees
11 May - 12 May
Bluegrass & Bourbon - a Peaceful Retreat & Hangout

Bourbon Blue - Toast Trailside with Family and Friends! 8 minutes from Downtown

2.0 star property
10.0 out of 10, Exceptional, (10)
"Spacious home, very clean, and an easy location to visit many establishments around Bardstown."
The price is AED 837
AED 2,081 total
includes taxes & fees
21 May - 22 May
Bourbon Blue - Toast Trailside with Family and Friends! 8 minutes from Downtown

Upscale 1 STORY 3 Bd 2 Ba on BOURBON TRAIL Close to Town 4 Beds/3 XL Beds + Q/S

10.0 out of 10, Exceptional, (67)
"Great location and accommodations would stay here again. "
The price is AED 738
AED 1,620 total
includes taxes & fees
28 Apr - 29 Apr
Upscale 1 STORY 3 Bd 2 Ba on BOURBON TRAIL Close to Town 4 Beds/3 XL Beds + Q/S

Hillside Home Close To The Bourbon Trail

8.6 out of 10, Excellent, (7)
"Perfect location and plenty of room for our whole party. Would stay again."
The price is AED 305
AED 1,166 total
includes taxes & fees
11 May - 12 May
Hillside Home Close To The Bourbon Trail

*NEW* Bourbon on Broadway- 3 King Bed- Downtown Bardstown

10.0 out of 10, Exceptional, (32)
"Great location in Bardstown. Clean and comfortable place to relax."
*NEW* Bourbon on Broadway- 3 King Bed- Downtown Bardstown

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

10.0 out of 10, Exceptional, (218)
"Fantastic location with great proximity to many places of interest. "
Luxurious 2BR /2Bath with Outdoor Courtyard and Garage in Downtown Bardstown

16 Mi to Louisville: Pet-Friendly Getaway!

10.0 out of 10, Exceptional, (6)
"Great place to stay"
16 Mi to Louisville: Pet-Friendly Getaway!

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

10.0 out of 10, Exceptional, (15)
"Property was very clean and well appointed. "
Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks

Historic Bardstown Cottage

10.0 out of 10, Exceptional, (51)
"The location of the cottage is perfect for a visit to many distilleries as well as things for a non-bourbon drinking wife to enjoy. Bardstown itself is a lovely town. "
Historic Bardstown Cottage

Spacious Home: 8 Mi to Bernheim Arboretum!

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice house in a centralized location for the places the group wanted to visit. Host receptive, checked in on us to make sure ok"
Spacious Home: 8 Mi to Bernheim Arboretum!

Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown

7.0 out of 10, Good, (2)
"Decent for a townhouse"
The price is AED 364
AED 664 total
includes taxes & fees
30 Apr - 1 May
Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown

My Kentucky Home on the Bourbon Trail

9.6 out of 10, Exceptional, (7)
"Nice location and clean place."
My Kentucky Home on the Bourbon Trail

Stunning view! Hot Tub, Privacy & Relaxation

2.0 star property
10.0 out of 10, Exceptional, (8)
"Awesome property with even better hosts. View is stunning and privacy is second to none. 10 out of 10 recommend and will stay again."
Stunning view! Hot Tub, Privacy & Relaxation
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 property types in Boston

3B/3B; Single Family Lakeside Retreat W/Hot Tub

9.6 out of 10, Exceptional, (45)
"Really loved the stay. The house was perfect for us."
3B/3B; Single Family Lakeside Retreat W/Hot Tub

A Room Off Broadway, a prime downtown hideaway

10.0 out of 10, Exceptional, (83)
"This was our first trip to Bardstown, and this room was the perfect location to downtown. Amy was very easy to communicate with. The room was super clean and comfy. We would definitely stay here again "
The price is AED 367
AED 587 total
includes taxes & fees
5 May - 6 May
A Room Off Broadway, a prime downtown hideaway

16 Mi to Louisville: Pet-Friendly Getaway!

10.0 out of 10, Exceptional, (6)
"Great place to stay"
16 Mi to Louisville: Pet-Friendly Getaway!
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.