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Boston Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Boston holiday rentals

Exterior

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, (127 reviews)
"Feels like home. "
United States
MARLENE G.
The price is HK$1,024
HK$1,691 total
includes taxes & fees
30 Aug - 31 Aug
One of a kind cabin in the woods. Quiet and private but close to everything.
Coffee/tea maker, fridge, microwave, oven

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

The E-Town Retreat 2BR townhouse close to Downtown
Elizabethtown
9.8 out of 10, Exceptional, (9 reviews)
"Nice place"
United States
Natalie G.
The price is HK$691
HK$1,412 total
includes taxes & fees
17 Aug - 18 Aug
The E-Town Retreat 2BR townhouse close to Downtown
Smart TV

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

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (12 reviews)
"Great stay! And great location! Very helpful and responsive hosts! "
United States
Kelsey T.
The price is HK$1,342
HK$3,175 total
includes taxes & fees
30 Aug - 31 Aug
Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Smart TV, DVD player, books

4. 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, (10 reviews)
"The home is quite comfortable and a nice, scenic property. There was very little road noise, providing an excellent night’s sleep. We would absolutely stay here again."
United States
Erin A.
The price is HK$1,024
HK$1,836 total
includes taxes & fees
29 Aug - 30 Aug
Lovely 3-bedroom home near the Bourbon Trail, with a lake in a country setting
Interior

5. The E-town Hideaway

The E-town Hideaway
Elizabethtown
9.6 out of 10, Exceptional, (10 reviews)
"Fantastic Experience in a beautiful home. Will be staying here again for sure. "
United States
ANDRAS J.
The E-town Hideaway
Outdoor dining

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$742
HK$1,250 total
includes taxes & fees
29 Aug - 30 Aug
On The Square!
Interior

7. Bourbon Oak Hideaway 1 - Charming Studio Apartment on the Bourbon Trail -

Bourbon Oak Hideaway 1 - Charming Studio Apartment on the Bourbon Trail -
Bardstown
10.0 out of 10, Exceptional, (4 reviews)
"We had extended family coming in from two different states, so renting the two units (Hideaway 1&2) together was a perfect solution. We had together time but plenty of privacy too. "
United States
Anonymous traveller
The price is HK$777
HK$1,964 total
includes taxes & fees
17 Aug - 18 Aug
Bourbon Oak Hideaway 1 - Charming Studio Apartment on the Bourbon Trail -
Coffee/tea maker, fridge, microwave, oven

8. 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, (23 reviews)
"Wonderful home with a great host!"
United States
Megan H.
The price is HK$565
HK$1,445 total
includes taxes & fees
15 Sept - 16 Sept
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff
Coffee/tea maker, fridge, microwave, oven

9. Lavish Rooftop Condo B with free ev charging for any vehicle

Lavish Rooftop Condo B with free ev charging for any vehicle
Elizabethtown
9.8 out of 10, Exceptional, (6 reviews)
"Clean condo with beautiful rooftop views and an easy walk to local restaurants. The host communicated quickly and was great to work with. Highly recommended!"
United States
Joel K.
The price is HK$1,138
HK$2,414 total
includes taxes & fees
17 Aug - 18 Aug
Lavish Rooftop Condo B with free ev charging for any vehicle
Terrace/patio

10. A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (135 reviews)
"Amazing stay all the way around! Would definitely plan to stay here again. "
United States
Matt R.
The price is HK$791
HK$1,348 total
includes taxes & fees
24 Aug - 25 Aug
A Room Off Broadway, a prime downtown hideaway
Coffee/tea maker, fridge, microwave, oven

11. New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (60 reviews)
"Easy parking, clean property, cool rooftop sitting area."
United States
Dawn C.
The price is HK$1,052
HK$2,207 total
includes taxes & fees
17 Aug - 18 Aug
New Downtown Luxury Townhouse in Bourbon Country
Exterior

12. Modern 3 bedroom house with AC in charming Elizabethtown with free Ev charging

Modern 3 bedroom house with AC in charming Elizabethtown with free Ev charging
Elizabethtown
10.0 out of 10, Exceptional, (7 reviews)
"Very easy process and will book again in the future"
United States
Clint K.
The price is HK$1,256
HK$2,561 total
includes taxes & fees
17 Aug - 18 Aug
Modern 3 bedroom house with AC in charming Elizabethtown with free Ev charging
Dining

13. 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$1,186
HK$2,556 total
includes taxes & fees
18 Aug - 19 Aug
Country Clean Cozy
2 bedrooms, WiFi, bed sheets

14. 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, (17 reviews)
"Cute place to stay in Bardstown!"
United States
Allison M.
The price is HK$812
HK$1,769 total
includes taxes & fees
24 Aug - 25 Aug
The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown
Property grounds

15. Bluegrass & Bourbon - a Peaceful Retreat & Hangout

Bluegrass & Bourbon - a Peaceful Retreat & Hangout
Bardstown
10.0 out of 10, Exceptional, (62 reviews)
"Wonderful home, great location, looking forward to our next stay!"
United States
Cathy C.
The price is HK$996
HK$3,087 total
includes taxes & fees
17 Aug - 18 Aug
Bluegrass & Bourbon - a Peaceful Retreat & Hangout
Coffee/tea maker, fridge, microwave, oven

16. “New” Elizabethtown Poplar Place!

“New” Elizabethtown Poplar Place!
Elizabethtown
10.0 out of 10, Exceptional, (33 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
17 Aug - 18 Aug
“New” Elizabethtown Poplar Place!
Exterior

17. Ron & Orline's Home, park at the door & use our EV 50 amp charger

Ron & Orline's Home, park at the door & use our EV 50 amp charger
Bardstown
10.0 out of 10, Exceptional, (166 reviews)
"Great place. Highly recommend "
United States
Matthew W.
The price is HK$1,216
HK$2,033 total
includes taxes & fees
17 Aug - 18 Aug
Ron & Orline's Home, park at the door & use our EV 50 amp charger
Exterior

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

Stay in a historic Early 1800s Guest House!
Bardstown
9.8 out of 10, Exceptional, (134 reviews)
"In easy walking distance of many downtown locations "
United States
Carol H.
The price is HK$812
HK$1,484 total
includes taxes & fees
18 Aug - 19 Aug
Stay in a historic Early 1800s Guest House!
Outdoor dining

19. Bourbon Country Cabin- Game Room, Fire Pit, and Hot Tub

Bourbon Country Cabin- Game Room, Fire Pit, and Hot Tub
Bardstown
10.0 out of 10, Exceptional, (24 reviews)
"Great house, relaxing environment, would definitely stay again!"
United States
Dustin S.
The price is HK$1,942
HK$4,918 total
includes taxes & fees
17 Aug - 18 Aug
Bourbon Country Cabin- Game Room, Fire Pit, and Hot Tub
Exterior

20. 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)
"This was the cleanest/nicest VRBO my family has stayed in. There were plenty of towels, hand soap at both sinks, TP, hangers, k-cups and so much more. I would definitely recommend this place and will definitely stay here again if we are ever in the area. Plenty of restaurants and shopping pretty close by."
United States
Teri B.
The price is HK$1,024
HK$2,693 total
includes taxes & fees
24 Aug - 25 Aug
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!
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

Distill-Inn

Distill-Inn

8/10 Good
"We enjoyed our overnight stay at the Distill Inn. Was very affordable and the staff helpful and pleasant."
Jay 1-night trip
Posted 1 hour ago
Distill-Inn

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
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  • 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?

Missy’s unique stays: This holiday home rental outside of Boston is located in a rural location, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Schmidt Museum of Coca Cola Memorabilia.

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.