Boston Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Boston holiday rentals

Living area

Spacious, Pristine Home w/ Firepit, Bourbon Lounge

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (4 reviews)
"Great stay! And great location! Very helpful and responsive hosts! "
United States
Kelsey T.
Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Outdoor dining

On The Square!

On The Square!
Elizabethtown
9.0 out of 10, Wonderful, (23 reviews)
"Great getaway! Host was amazing and welcoming! "
United States
nicole g.
The price is HK$740
HK$1,247 total
includes taxes & fees
29 Mar - 30 Mar
On The Square!
Terrace/patio

A Bourbon Connoisseur's dream is where you will find Rolling Fork Farm

A Bourbon Connoisseur's dream is where you will find Rolling Fork Farm
Campbellsville
10.0 out of 10, Exceptional, (15 reviews)
"This cabin was awesome, and had all the amenities you need!"
United States
Matt C.
The price is HK$2,544
HK$5,188 total
includes taxes & fees
30 Mar - 31 Mar
A Bourbon Connoisseur's dream is where you will find Rolling Fork Farm
Exterior

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, (114 reviews)
"Everything here was very well done. A perfect place for a couples get away. Super clean and really liked the layout.This will be our go-to when visiting Bardstown!"
United States
Rick W.
The price is HK$1,120
HK$1,761 total
includes taxes & fees
1 Apr - 2 Apr
One of a kind cabin in the woods. Quiet and private but close to everything.
Interior

Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!

Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!
3.0 star property
Vine Grove
10.0 out of 10, Exceptional, (4 reviews)
"The house was perfect for our short visit with our son at Ft. Knox. The house was small but clean and well maintained. The layout made good use of the space and everything was in working order. Overall a great option for someone looking for a place to stay. "
United States
ANDREA
The price is HK$767
HK$2,077 total
includes taxes & fees
29 Mar - 30 Mar
Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!
Smart TV, DVD player, books, music library

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

Upscale 1 STORY 3 Bd 2 Ba on BOURBON TRAIL Close to Town 4 Beds/3 XL Beds + Q/S
Bardstown
10.0 out of 10, Exceptional, (84 reviews)
"Excellent location to everything! "
United States
Melissa R.
The price is HK$1,430
HK$3,242 total
includes taxes & fees
30 Mar - 31 Mar
Upscale 1 STORY 3 Bd 2 Ba on BOURBON TRAIL Close to Town 4 Beds/3 XL Beds + Q/S
Pool

Kentucky Sunrise 18- Greet the Sun As it Rises

Kentucky Sunrise 18- Greet the Sun As it Rises
Taylorsville
9.8 out of 10, Exceptional, (51 reviews)
"Quiet, peaceful place to rest. Perfect for a weekend getaway"
United States
Ryan D.
The price is HK$1,057
HK$2,437 total
includes taxes & fees
26 Mar - 27 Mar
Kentucky Sunrise 18- Greet the Sun As it Rises
Pool

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB
Taylorsville
9.8 out of 10, Exceptional, (24 reviews)
"Very nice house, new hot tub in the resort it was located in was very nice"
United States
Mike O.
Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB
Terrace/patio

Cozy KY Escape with Hot Tub near the Bourbon Trail

Cozy KY Escape with Hot Tub near the Bourbon Trail
Taylorsville
10.0 out of 10, Exceptional, (106 reviews)
"The cottage is very clean and comfortable. I stayed with a friend and we were both impressed by how comfortable the beds are. The area the cottage is in is very pretty. I didn't stay long because I was in and out for a wedding, but I would definitely book this cottage again."
United States
Rachel I.
The price is HK$1,479
HK$2,727 total
includes taxes & fees
26 Mar - 27 Mar
Cozy KY Escape with Hot Tub near the Bourbon Trail
Smart TV, fireplace

Bourbon Oak Hideaway 2 offers a 2 bed 2.5 bath apartment in historic Bardstown.

Bourbon Oak Hideaway 2 offers a 2 bed 2.5 bath apartment in historic Bardstown.
Bardstown
9.8 out of 10, Exceptional, (6 reviews)
"Nice rooms & very clean "
United States
jim W.
The price is HK$1,166
HK$2,425 total
includes taxes & fees
26 Mar - 27 Mar
Bourbon Oak Hideaway 2 offers a 2 bed 2.5 bath apartment in historic Bardstown.
Exterior

Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake

Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake
Magnolia
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place!"
United States
Scott B.
The price is HK$1,057
HK$1,978 total
includes taxes & fees
26 Mar - 27 Mar
Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake
Exterior

Justin Fitch Cabin - Active Heroes

Justin Fitch Cabin - Active Heroes
Bullitt County
Justin Fitch Cabin - Active Heroes
Fridge, microwave, oven, stovetop

Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck

Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck
Springfield
9.8 out of 10, Exceptional, (17 reviews)
"Great home and layout in the peaceful countryside!"
United States
John P.
The price is HK$1,409
HK$3,369 total
includes taxes & fees
3 Apr - 4 Apr
Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck
Fridge, microwave, oven, stovetop

StillHill: HotTub GameRoom Whiskey Lounge Acreage

StillHill: HotTub GameRoom Whiskey Lounge Acreage
Bardstown
9.8 out of 10, Exceptional, (10 reviews)
"The place was great. Comfortable accomodations and would visit again!"
United States
Alan R.
The price is HK$1,566
HK$2,990 total
includes taxes & fees
8 Apr - 9 Apr
StillHill: HotTub GameRoom Whiskey Lounge Acreage
Interior

The Elizabethtown Hideaway

The Elizabethtown Hideaway
Elizabethtown
10.0 out of 10, Exceptional, (6 reviews)
"Fantastic Experience in a beautiful home. Will be staying here again for sure. "
United States
ANDRAS J.
The Elizabethtown Hideaway
Property grounds

Modern 2 Bed Suite on Bourbon Trail

Modern 2 Bed Suite on Bourbon Trail
Loretto
10.0 out of 10, Exceptional, (29 reviews)
"The location was perfect, the host was responsive and helpful, the room was super clean, the bed was very comfortable, and all of the little extras were so thoughtful. It was truly a perfect stay."
United States
Lisa P.
The price is HK$648
HK$1,105 total
includes taxes & fees
6 Apr - 7 Apr
Modern 2 Bed Suite on Bourbon Trail
Terrace/patio

A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (118 reviews)
"The room was awesome and it felt very secluded. Amy was amazing and id highly recommend!"
United States
Beth
The price is HK$705
HK$1,165 total
includes taxes & fees
30 Mar - 31 Mar
A Room Off Broadway, a prime downtown hideaway
Interior

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

Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!
Springfield
10.0 out of 10, Exceptional, (10 reviews)
"We loved our stay!"
United States
Marymae H.
The price is HK$1,213
HK$2,221 total
includes taxes & fees
21 Apr - 22 Apr
Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!
Property grounds

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, (161 reviews)
"Close to distilleries, clean and comfortable"
United States
Eddie
The price is HK$1,213
HK$1,993 total
includes taxes & fees
29 Mar - 30 Mar
Ron & Orline's Home, park at the door & use our EV 50 amp charger
Exterior

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
The price is HK$1,252
HK$2,433 total
includes taxes & fees
25 Apr - 26 Apr
Modern 3 bedroom house with AC in charming Elizabethtown with free Ev charging
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

Talbott Inn

Talbott Inn

8/10 Good
"The staff was friendly and helpful. Our room was very clean and had a lot of charm. The bathroom was small, but adequate. The shower water pressure left a lot to be desired. It’s a very old building which is part of its charm. One issue.. They were having construction work done and all the parking was roped off. It started the day before we checked out. We should have been informed of where to park. One of the construction team directed us. Other than that, our stay was delightful.."
Kathleen 3-night trip
Posted 2 hours ago
Talbott 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:

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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?

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65: This holiday home rental outside of Boston is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Spalding Hall.

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.