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Boston Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Boston holiday rentals

A living room with a gray sectional sofa, a wooden coffee table, and a framed map on the wall.

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

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (18 reviews)
"Very clean and spacious. We really enjoyed are stay."
United States
Pamela W.
The price is AU$597
includes taxes & fees
3 Nov - 4 Nov
Spacious, Pristine Home w/ Firepit, Bourbon Lounge
A wooden gazebo with string lights, outdoor seating, and a fire pit in a grassy backyard.

2. Ultimate Bardstown Oasis | Pool, Tub, Game Lounge!

Ultimate Bardstown Oasis | Pool, Tub, Game Lounge!
Bardstown
The price is AU$1,125
includes taxes & fees
1 Nov - 2 Nov
Ultimate Bardstown Oasis | Pool, Tub, Game Lounge!
A cozy living room with two armchairs, a small table, and a view of a wooden deck with outdoor furniture.

3. 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, (13 reviews)
"The stay was amazing. The property was exactley ascdescribed. We enjoyed our stay very much."
United States
Beverly R.
The price is AU$373
includes taxes & fees
29 Nov - 30 Nov
Lovely 3-bedroom home near the Bourbon Trail, with a lake in a country setting
A small, single-story cabin with a metal exterior, surrounded by trees and a wooden deck.

4. 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, (134 reviews)
"Feels like home. "
United States
MARLENE G.
The price is AU$280
includes taxes & fees
2 Nov - 3 Nov
One of a kind cabin in the woods. Quiet and private but close to everything.
A backyard with a fire pit, outdoor seating, and a covered patio area.

5. Bourbon Trailhead Bardstown

Bourbon Trailhead Bardstown
Bardstown
10.0 out of 10, Exceptional, (8 reviews)
"Brooke and Dave have a wonderful property in the heart of bourbon country. They communicated clearly and responsively about our stay. The house was perfect for our time exploring Bardstown and the surrounding area. So many distilleries were between 10-50 minutes away. No chance to experience them all. The home is roomy and designed with our enjoyment in mind: from the cozy lower level with pool table, shuffle board and game cabinet to the main floor with massive TV and 2 video game...
United States
Anonymous traveller
The price is AU$981
includes taxes & fees
30 Oct - 31 Oct
Bourbon Trailhead Bardstown
A wooden deck with a hot tub, outdoor seating, and a wooden house in the background.

6. 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, (30 reviews)
"Great place to stay"
United States
Benjamin P.
The price is AU$947
includes taxes & fees
3 Nov - 4 Nov
Bourbon Country Cabin- Game Room, Fire Pit, and Hot Tub
A hotel room with two beds, a TV, a microwave, and a desk.

7. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Shepherdsville
10.0 out of 10, Exceptional, (98 reviews)
"We felt so relaxed during our stay"
United States
Anonymous traveller
The price is AU$91
includes taxes & fees
1 Nov - 2 Nov
2 Queen Beds | Non-Smoking
A two-story house with a covered porch and outdoor seating area.

8. Hot Tub- Sleeps 10- Bourbon Trail- Historic Home

Hot Tub- Sleeps 10- Bourbon Trail- Historic Home
Coxs Creek
10.0 out of 10, Exceptional, (28 reviews)
"We stayed here on a girl’s getaway and were very pleased with the accommodations!"
United States
Cathy A.
The price is AU$441
includes taxes & fees
12 Nov - 13 Nov
Hot Tub- Sleeps 10- Bourbon Trail- Historic Home
A hallway with wooden flooring, white walls, and doors leading to individual rooms.

9. The E-town Exclusive B

The E-town Exclusive B
Elizabethtown
9.4 out of 10, Exceptional, (3 reviews)
"Property was clean and convenient to where I needed to be I will be staying there again"
United States
JEFF
The price is AU$286
includes taxes & fees
29 Nov - 30 Nov
The E-town Exclusive B
A living room with a sectional sofa, a fireplace, and a television mounted on the wall.

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

Stay downtown within walking distance of restaurants, shopping, and breweries!
Bardstown
9.4 out of 10, Exceptional, (98 reviews)
"Completely charming and very close to everything!"
United States
Susan M.
The price is AU$375
includes taxes & fees
1 Nov - 2 Nov
Stay downtown within walking distance of restaurants, shopping, and breweries!
A modern kitchen with a central island, stainless steel appliances, and a chandelier.

11. Country Clean Cozy

Country Clean Cozy
Elizabethtown
9.6 out of 10, Exceptional, (49 reviews)
"Great place to stay while visiting friends who live locally."
United States
Kyla C.
Country Clean Cozy
A living room with a brick wall, a fireplace, a large clock, and a leather sofa.

12. 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, (181 reviews)
"Stairs were a little crazy but great location!"
United States
Amy A.
The price is AU$316
includes taxes & fees
1 Nov - 2 Nov
Beautiful apartment in the heart of downtown Bardstown, KY
A covered patio with a grill, outdoor seating, and potted plants.

13. A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (145 reviews)
"Great place and great location! We love it here!"
United States
Harlan K.
The price is AU$247
includes taxes & fees
1 Nov - 2 Nov
A Room Off Broadway, a prime downtown hideaway
A hotel room with a bed, a desk, a chair, a TV, and a window with curtains.

14. 1 King Bed Non-Smoking

1 King Bed Non-Smoking
Shepherdsville
10.0 out of 10, Exceptional, (100 reviews)
"We had a great time staying here"
United States
Anonymous traveller
The price is AU$83
includes taxes & fees
30 Oct - 31 Oct
1 King Bed Non-Smoking
An outdoor seating area with wooden tables and chairs, a mural of clocks on the wall, and hanging plants.

15. On The Square!

On The Square!
Elizabethtown
9.2 out of 10, Wonderful, (30 reviews)
"cute little place close walk to great food."
United States
Jerry B.
The price is AU$230
includes taxes & fees
31 Oct - 1 Nov
On The Square!
A red door with a small window above it, a mailbox, and two potted plants on the ground.

16. Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY

Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY
Bardstown
10.0 out of 10, Exceptional, (264 reviews)
"Nice place to stay you can walk anywhere."
United States
Chris B.
The price is AU$404
includes taxes & fees
4 Nov - 5 Nov
Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY
A modern kitchen with dark cabinetry, a stainless steel refrigerator, a granite countertop, and a black trash bin.

17. New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (63 reviews)
"Highly recommend!"
United States
Hallie D.
The price is AU$391
includes taxes & fees
30 Oct - 31 Oct
New Downtown Luxury Townhouse in Bourbon Country
A single-story house with a front porch, a stone foundation, and a small front yard.

18. 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, (10 reviews)
"Very easy process and will book again in the future"
United States
Clint K.
The price is AU$449
includes taxes & fees
30 Oct - 31 Oct
Modern 3 bedroom house with AC in charming Elizabethtown with free Ev charging
A bedroom with a bed, a nightstand, a dresser, and a closet with sliding doors.

19. Apartment Downtown Bardstown<br>The PACK

Apartment Downtown Bardstown<br>The PACK
Bardstown
9.8 out of 10, Exceptional, (85 reviews)
"Very nice accommodations that keep you right in the heart of Bardstown."
United States
Kim A.
The price is AU$376
includes taxes & fees
1 Nov - 2 Nov
Apartment Downtown Bardstown<br>The PACK
A living room with a sofa, coffee table, and a dining area with stools and a table.

20. Hillside Home on the KY Bourbon Trail Sleeps 6

Hillside Home on the KY Bourbon Trail Sleeps 6
Bardstown
9.0 out of 10, Wonderful, (8 reviews)
"Cozy place with charm. Great location for bourbon trail activities."
United States
Aaron S.
The price is AU$510
includes taxes & fees
16 Nov - 17 Nov
Hillside Home on the KY Bourbon Trail Sleeps 6
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

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

8/10 Good
"Staff was great, Breakfast was good. Would stay again. Issues 1) Shower curtain was way too long for the tub as I kept stepping on it taking a shower. 2) Said there was deli on site according to Expedia booking and there was not. Snacks is it"
Jason 1-night trip
Posted 9 hours ago
Greenfield Inn and Suites Elizabethtown, KY I65 Exit 94

Find out more about Boston

Everything you need to know about Boston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Boston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Boston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Boston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Boston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Boston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Boston holiday rentals we have selected for you start as low as AU$83 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Boston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.