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Boston Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Boston holiday rentals

A small, single-story cabin with a metal exterior, surrounded by trees and a wooden deck.

1. One of a kind cabin in the woods. Quiet and private but close to everything.

One of a kind cabin in the woods. Quiet and private but close to everything.
Coxs Creek
10.0 out of 10, Exceptional, (131 reviews)
"Feels like home. "
United States
MARLENE G.
The price is HK$932
HK$1,555 total
includes taxes & fees
6 Oct - 7 Oct
One of a kind cabin in the woods. Quiet and private but close to everything.
A kitchen with white cabinets, a black refrigerator, a stove, and a dishwasher.

2. The E-Town Retreat 2BR townhouse close to Downtown

The E-Town Retreat 2BR townhouse close to Downtown
Elizabethtown
9.6 out of 10, Exceptional, (11 reviews)
"Nice place"
United States
Natalie G.
The price is HK$690
HK$1,403 total
includes taxes & fees
1 Oct - 2 Oct
The E-Town Retreat 2BR townhouse close to Downtown
A modern kitchen with white cabinets, a black countertop, and a stainless steel refrigerator.

3. Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff
Radcliff
9.8 out of 10, Exceptional, (25 reviews)
"Wonderful home with a great host!"
United States
Megan H.
The price is HK$565
HK$1,444 total
includes taxes & fees
5 Oct - 6 Oct
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff
A modern kitchen with a central island, stainless steel appliances, and a chandelier.

4. Country Clean Cozy

Country Clean Cozy
Elizabethtown
9.6 out of 10, Exceptional, (45 reviews)
"Great place to stay while visiting friends who live locally."
United States
Kyla C.
The price is HK$856
HK$2,234 total
includes taxes & fees
4 Oct - 5 Oct
Country Clean Cozy
A modern living room with a leather sofa, a coffee table, and a rustic barrel. A kitchen is visible in the background, and a 'WELCOME' sign is on the wall.

5. NEW “Bourbon on the Square” Downtown Rustic Loft

NEW “Bourbon on the Square” Downtown Rustic Loft
Elizabethtown
10.0 out of 10, Exceptional, (28 reviews)
"This was a very great spot for my wife and I stay while visiting Elizabethtown. It really checked all the boxes for us. Perfect size, very well decorated, and close to a lot of good shops and restaurants. It also is nearby many great bourbon distilleries. I highly recommend this property if you are visiting the area."
United States
Ben S.
The price is HK$882
HK$1,699 total
includes taxes & fees
4 Oct - 5 Oct
NEW “Bourbon on the Square” Downtown Rustic Loft
An outdoor seating area with wooden tables and chairs, a mural of clocks on the wall, and hanging plants.

6. On The Square!

On The Square!
Elizabethtown
9.2 out of 10, Wonderful, (29 reviews)
"Perfect little hidden gem! And walking distance to EVERYTHING!"
United States
Katie W.
The price is HK$741
HK$1,250 total
includes taxes & fees
1 Oct - 2 Oct
On The Square!
A covered patio with a grill, outdoor seating, and potted plants.

7. A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (143 reviews)
"Great place and great location! We love it here!"
United States
Harlan K.
The price is HK$791
HK$1,348 total
includes taxes & fees
4 Oct - 5 Oct
A Room Off Broadway, a prime downtown hideaway
A two-story brick house with a front entrance, a small front yard with plants, and a clear blue sky.

8. Stay in a historic Early 1800s Guest House!

Stay in a historic Early 1800s Guest House!
Bardstown
9.8 out of 10, Exceptional, (138 reviews)
"Cute little place, convenient to downtown, shower was a little short lol"
United States
Joshua P.
The price is HK$812
HK$1,483 total
includes taxes & fees
5 Oct - 6 Oct
Stay in a historic Early 1800s Guest House!
A bedroom with a bed, bedside tables, a ceiling fan, a door, and a framed picture on the wall.

9. The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown

The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown
Bardstown
10.0 out of 10, Exceptional, (24 reviews)
"Cute place to stay in Bardstown!"
United States
Allison M.
The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown
A modern kitchen with white cabinetry, a built-in oven, and a large window.

10. Old Maple House -touch of Canadian charm on Kentuckys Bourbon Trail. Circa 1901.

Old Maple House -touch of Canadian charm on Kentuckys Bourbon Trail. Circa 1901.
Elizabethtown
10.0 out of 10, Exceptional, (33 reviews)
"Charming house in great location. It truly had everything we needed for a comfortable and relaxing stay. Will definitely stay there again!"
United States
Terri T.
The price is HK$863
HK$2,063 total
includes taxes & fees
4 Oct - 5 Oct
Old Maple House -touch of Canadian charm on Kentuckys Bourbon Trail. Circa 1901.
A living room with two sofas, a coffee table, a lamp, and a painting on the wall.

11. The E-town Exclusive B

The E-town Exclusive B
Elizabethtown
The price is HK$659
HK$1,464 total
includes taxes & fees
4 Oct - 5 Oct
The E-town Exclusive B
A cozy living room with two armchairs, a small table, and a view of a wooden deck with outdoor furniture.

12. Lovely 3-bedroom home near the Bourbon Trail, with a lake in a country setting

Lovely 3-bedroom home near the Bourbon Trail, with a lake in a country setting
New Haven
10.0 out of 10, Exceptional, (11 reviews)
"The stay was amazing. The property was exactley ascdescribed. We enjoyed our stay very much."
United States
Beverly R.
The price is HK$1,138
HK$1,949 total
includes taxes & fees
25 Oct - 26 Oct
Lovely 3-bedroom home near the Bourbon Trail, with a lake in a country setting
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

13. The Maple Den

The Maple Den
Elizabethtown
9.8 out of 10, Exceptional, (25 reviews)
"What great place. It was clean and very beautiful. The host was easy to talk to and responded favorably to every request. We would definitely stay here again every time we are in town."
United States
David M.
The price is HK$847
HK$2,225 total
includes taxes & fees
4 Oct - 5 Oct
The Maple Den
A modern kitchen with dark cabinetry, a stainless steel refrigerator, a granite countertop, and a black trash bin.

14. New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (62 reviews)
The price is HK$1,052
HK$2,189 total
includes taxes & fees
1 Oct - 2 Oct
New Downtown Luxury Townhouse in Bourbon Country
A living room with a brick wall, a fireplace, a large clock, and a leather sofa.

15. Beautiful apartment in the heart of downtown Bardstown, KY

Beautiful apartment in the heart of downtown Bardstown, KY
Bardstown
9.4 out of 10, Exceptional, (177 reviews)
"Very quaint apartment, everything we needed for a one night stay."
United States
Leslie R.
The price is HK$918
HK$1,730 total
includes taxes & fees
5 Oct - 6 Oct
Beautiful apartment in the heart of downtown Bardstown, KY
A modern kitchen with a large island, wooden cabinets, and a stainless steel refrigerator.

16. New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country

New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country
New Hope
10.0 out of 10, Exceptional, (69 reviews)
"Excellent location with easy access to Bardstown and distilleries. Well equipped bar for home tasting as well as games and entertainment. We had a great stay!"
United States
Patrick M.
The price is HK$939
HK$2,333 total
includes taxes & fees
12 Oct - 13 Oct
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

17. “New” Elizabethtown Poplar Place!

“New” Elizabethtown Poplar Place!
Elizabethtown
10.0 out of 10, Exceptional, (35 reviews)
"Relatively quiet neighborhood with quick access to downtown. We loved the screened in porch and spent a lot of time out there!"
United States
MacKenzie S.
The price is HK$1,010
HK$2,056 total
includes taxes & fees
4 Oct - 5 Oct
“New” Elizabethtown Poplar Place!
A living room with a gray sectional sofa, a wooden coffee table, and a framed map on the wall.

18. Spacious, Pristine Home w/ Firepit, Bourbon Lounge

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (15 reviews)
Spacious, Pristine Home w/ Firepit, Bourbon Lounge
A modern building with a large garage door, a small porch with a bench, and a garden area with plants and pebbles.

19. Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!

Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!
Elizabethtown
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful place to stay!! "
United States
Gracie T.
The price is HK$1,024
HK$2,692 total
includes taxes & fees
5 Oct - 6 Oct
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!
Room

20. Welcoming Downtown Single Private Upstairs Apartment

Welcoming Downtown Single Private Upstairs Apartment
Elizabethtown
The price is HK$763
HK$1,602 total
includes taxes & fees
4 Oct - 5 Oct
Welcoming Downtown Single Private Upstairs Apartment
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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Top Boston Hotel Reviews

The Trail Hotel

The Trail Hotel

10/10 Excellent
"The hotel was surprisingly modern and very well updated. The room was clean and state of the art. We very much enjoyed our stay while doing the Bourbon trail."
Diana 1-night trip
Posted 2 hours ago
The Trail Hotel

Find out more about Boston

Search for holiday rentals in Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in Boston using one of the methods below:

  • View our selection of featured holiday rentals in Boston
  • Use the map to find apartments and other holiday homes in the Boston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Boston while they last

Look no further and take a look at our great range of rental properties in Boston!

Frequently asked questions

Can I find holiday rentals in Boston?

Yes, there are holiday rentals close to the most popular sights in Boston, 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 Boston has to offer?

Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!: This holiday home rental outside of Boston offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Boston?

Explore the area and family-friendly sights such as Kentucky Railway Museum, or get out into nature at a spot like Bernheim Arboretum and Research Forest. In the wider area, you’ll find Jim Beam American Outpost and Bardstown Art Gallery.

What’s a holiday rental in Boston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Boston. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family gatherings.