Boston Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Boston

Our top choices for Boston holiday rentals

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

10.0 out of 10, Exceptional, (221)
"This property was perfect for our trip to bourbon country! We could walk to many restaurants and shops in Bardstown. Parking was close and easy. Clean, comfortable and a cute welcome gift along with light snacks provided. We would gladly stay here again. "
The price is AU$444
includes taxes & fees
8 Sept - 9 Sept
Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY

Nice log cabin home in the heart of bourbon country. Pet friendly.

10.0 out of 10, Exceptional, (5)
The price is AU$256
includes taxes & fees
3 Sept - 4 Sept
Nice log cabin home in the heart of bourbon country. Pet friendly.

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

10.0 out of 10, Exceptional, (94)
"Everything from top to bottom was fantastic about this property. The location was perfectly located to be able to go into Louisville or Bardstown. "
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

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

10.0 out of 10, Exceptional, (154)
"Like visiting Grandma's house while super close to all the bourbon awesomeness"
The price is AU$398
includes taxes & fees
9 Sept - 10 Sept
Ron & Orline's Home, park at the door & use our EV 50 amp charger

Downtown Bourbon Black Swan House

9.8 out of 10, Exceptional, (12)
"Loved staying here! So close to downtown-we were able to walk everywhere we wanted. The house is so nice. I would definitely stay here again and recommend highly!"
The price is AU$517
includes taxes & fees
9 Sept - 10 Sept
Downtown Bourbon Black Swan House

Modern 2 Bed Suite on Bourbon Trail

2.0 star property
10.0 out of 10, Exceptional, (15)
"We really enjoyed our stay. The owner was awesome to work with!"
The price is AU$193
includes taxes & fees
3 Sept - 4 Sept
Modern 2 Bed Suite on Bourbon Trail

NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

10.0 out of 10, Exceptional, (2)
"Host provided great communication before and after our stay. Super great location for anyone visiting the Bourbon Trail. Thank you for making our stay in Kentucky such a great experience for everyone!"
The price is AU$1,072
includes taxes & fees
9 Sept - 10 Sept
NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

Stay in a historic Early 1800s Guest House!

10.0 out of 10, Exceptional, (105)
"We loved the guest house, and the location could not be beat! Just a block walk to the lovely downtown. The guest house had everything we needed for a comfortable, nice visit to Bardstown."
The price is AU$311
includes taxes & fees
22 Sept - 23 Sept
Stay in a historic Early 1800s Guest House!

The Farmwife’s Hideaway

10.0 out of 10, Exceptional, (28)
"We visited for a long weekend, great place to stay! Lots of space for everyone and a great outdoor space to also enjoy our evenings. Definitely plan to go back!"
The price is AU$481
includes taxes & fees
3 Sept - 4 Sept
The Farmwife’s Hideaway

Cozy cottage in charming New Hope with AC, WiFi

9.8 out of 10, Exceptional, (10)
"Perfect little cottage to unwind in after a day on the road. Clean and the bed is super comfy. Situated close to the Bourbon Trail distilleries. Our hosts (Jon and Robin) really paid attention to details from the bottled water in the frig to the coffee pods for the Keurig. We will definitely stay again when we're in the area."
The price is AU$281
includes taxes & fees
1 Oct - 2 Oct
Cozy cottage in charming New Hope with AC, WiFi

Stunning view! Hot Tub, Privacy & Relaxation

2.0 star property
10.0 out of 10, Exceptional, (16)
"Awesome place. Very clean. Very peaceful and relaxing "
Stunning view! Hot Tub, Privacy & Relaxation

A Room Off Broadway, a prime downtown hideaway

10.0 out of 10, Exceptional, (98)
"Great space, clean and perfect size for the two of us (adults). Definitely recommend the property and the town"
The price is AU$230
includes taxes & fees
8 Sept - 9 Sept
A Room Off Broadway, a prime downtown hideaway

Beautiful apartment in the heart of downtown Bardstown, KY

9.6 out of 10, Exceptional, (145)
"Host hospitality was great, coffee, pancake mix and eggs available. Location is great. Located on second floor, if you have larger luggage."
The price is AU$339
includes taxes & fees
14 Sept - 15 Sept
Beautiful apartment in the heart of downtown Bardstown, KY

Quaint,newly remodeled country cabin in the heart of Bourbon Country.

2.0 star property
9.8 out of 10, Exceptional, (7)
"Quaint, recently updated place in the heart of bourbon country! Quiet stay, scenic area!"
Quaint,newly remodeled country cabin in the heart of Bourbon Country.

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

9.6 out of 10, Exceptional, (76)
"This place is just adorable and perfect location! "
The price is AU$326
includes taxes & fees
3 Sept - 4 Sept
Stay downtown within walking distance of restaurants, shopping, and breweries!

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

10.0 out of 10, Exceptional, (55)
"Great place to stay while doing a Bourbon Tour!!"
The price is AU$457
includes taxes & fees
3 Sept - 4 Sept
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country

Apartment Downtown Bardstown<br>The PACK

9.8 out of 10, Exceptional, (57)
"Such a beautifully decorated and easy location in Bardstown. We enjoyed our stay very much. "
The price is AU$369
includes taxes & fees
7 Sept - 8 Sept
Apartment Downtown Bardstown<br>The PACK

Call Me Old Fashioned! *Heart of Bardstown Square*

10.0 out of 10, Exceptional, (44)
"Very comfortable and welcoming accommodation for our party of six to enjoy Bourbon Country from. Perfectly walkable to Bardstown’s lovely downtown. "
The price is AU$1,303
includes taxes & fees
3 Sept - 4 Sept
Call Me Old Fashioned! *Heart of Bardstown Square*

Explore Bardstown's bourbon heritage - Heaven Hill just 13 minutes away

2.0 star property
10.0 out of 10, Exceptional, (6)
"Exactly as described, was perfect for our family. Alan was great at communicating and giving places to eat at."
The price is AU$602
includes taxes & fees
10 Sept - 11 Sept
Explore Bardstown's bourbon heritage - Heaven Hill just 13 minutes away

Historic Bardstown Cottage

10.0 out of 10, Exceptional, (57)
"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
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Boston Hotel Reviews

Find out more about Boston

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$193 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?

NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown: This holiday home rental outside of Boston offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 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.