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Boston Holiday Rentals

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Our top choices for Boston holiday rentals

The E-Town Retreat 2BR townhouse close to Downtown

The E-Town Retreat 2BR townhouse close to Downtown
Elizabethtown
10.0 out of 10, Exceptional, (5 reviews)
"The host was very welcoming and accomadating. We were travelling for a sad reason, a death in the family. It was nice to have a comfortable quiet place to stay. "
United States
Leanna H.
The price is AU$256
includes taxes & fees
16 June - 17 June
The E-Town Retreat 2BR townhouse close to Downtown

Cozy Bourbon Trail Loft suite in Loretto

Cozy Bourbon Trail Loft suite in Loretto
Loretto
9.8 out of 10, Exceptional, (9 reviews)
"Amazing host, place was super clean, conveniently located, place had everything you would need for a trip. I would highly recommend checking this place out."
United States
Andrea E
The price is AU$236
includes taxes & fees
18 June - 19 June
Cozy Bourbon Trail Loft suite in Loretto

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, (3 reviews)
"Awesome place!"
United States
Scott B.
The price is AU$362
includes taxes & fees
23 June - 24 June
Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake

On The Square!

On The Square!
Elizabethtown
9.0 out of 10, Wonderful, (24 reviews)
"Wonderful stay, everything was just perfect. We walked to a delicious pizza restaurant and then to a concert at the Theater nearby. Host was great with communication and provided everything we needed. "
United States
Randi K.
The price is AU$231
includes taxes & fees
13 June - 14 June
On The Square!

Spacious, Pristine Home w/ Firepit, Bourbon Lounge

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (10 reviews)
"Great stay! And great location! Very helpful and responsive hosts! "
United States
Kelsey T.
The price is AU$572
includes taxes & fees
14 June - 15 June
Spacious, Pristine Home w/ Firepit, Bourbon Lounge

Modern 2 Bed Suite on Bourbon Trail

Modern 2 Bed Suite on Bourbon Trail
Loretto
10.0 out of 10, Exceptional, (30 reviews)
"Excellent accomodations. Well-priced with a great kitchen, more TVs than you could possibly ever dream possible, comfy outdoor seating, and so much more. Jeff is an incredible host who goes above and beyond."
United States
Russell
The price is AU$206
includes taxes & fees
16 June - 17 June
Modern 2 Bed Suite on Bourbon Trail

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)
"Great location and the host was so wonderful! Will definitely stay again! "
United States
Lucy W.
The price is AU$348
includes taxes & fees
14 June - 15 June
Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!

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, (165 reviews)
"Close to distilleries, clean and comfortable"
United States
Eddie
The price is AU$365
includes taxes & fees
24 June - 25 June
Ron & Orline's Home, park at the door & use our EV 50 amp charger

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, (5 reviews)
The price is AU$458
includes taxes & fees
13 July - 14 July
Modern 3 bedroom house with AC in charming Elizabethtown with free Ev charging

Cozy cottage in charming New Hope with AC, WiFi

Cozy cottage in charming New Hope with AC, WiFi
New Hope
10.0 out of 10, Exceptional, (17 reviews)
"The owners went above and beyond during our stay. This place is a true gem! The cottage has everything you need and the bed was super comfy!"
United States
Megan B.
The price is AU$265
includes taxes & fees
1 July - 2 July
Cozy cottage in charming New Hope with AC, WiFi

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, (163 reviews)
"Host responded quickly when questions were asked! Very clean, plenty of bedding, kitchen stocked well! Location is Fabulous!! "
United States
Anonymous traveller
The price is AU$320
includes taxes & fees
14 June - 15 June
Beautiful apartment in the heart of downtown Bardstown, KY

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, (121 reviews)
"Great stay. "
United States
Royce
The price is AU$360
includes taxes & fees
26 June - 27 June
One of a kind cabin in the woods. Quiet and private but close to everything.

One-level Family Retreat I Game Room I Bourbon Trail

One-level Family Retreat I Game Room I Bourbon Trail
Lebanon
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable home to stay while we were in town for our daughter’s wedding at Bradsfordsville Manor. Beds comfortable, directions easily accessible and it felt like home. "
United States
Tammie T.
The price is AU$330
includes taxes & fees
12 July - 13 July
One-level Family Retreat I Game Room I Bourbon Trail

The Rustic Suite on Bourbon Trail

The Rustic Suite on Bourbon Trail
Loretto
9.6 out of 10, Exceptional, (33 reviews)
"It was perfect!! "
United States
Shana S.
The price is AU$218
includes taxes & fees
17 June - 18 June
The Rustic Suite on Bourbon Trail

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, (24 reviews)
"Such a beautiful place to stay!! "
United States
Gracie T.
The price is AU$492
includes taxes & fees
14 June - 15 June
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!

NEW “Bourbon on the Square” Downtown Rustic Loft

NEW “Bourbon on the Square” Downtown Rustic Loft
Elizabethtown
10.0 out of 10, Exceptional, (24 reviews)
"We enjoyed our stay in Elizabethtown, Todd was very accommodating and the place was as advertised. The location was great, with lots of restaurants and shopping within walking distance. Highly recommended if you are planning a trip to the area."
United States
Dan
The price is AU$295
includes taxes & fees
14 June - 15 June
NEW “Bourbon on the Square” Downtown Rustic Loft

Elizabethtown Charm

Elizabethtown Charm
Elizabethtown
9.8 out of 10, Exceptional, (20 reviews)
"It was a very nice property and we enjoyed the stay. "
United States
William L.
The price is AU$298
includes taxes & fees
14 June - 15 June
Elizabethtown Charm

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, (16 reviews)
"Host was very helpful, we got snowed in and forced to stay an extra day and the host continued to check on us to make sure we were good!"
United States
Thomas O.
The price is AU$281
includes taxes & fees
22 June - 23 June
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (58 reviews)
"Very nice place in the heart of downtown. Host was easy to communicate with. Would stay there again."
United States
Justin F.
The price is AU$401
includes taxes & fees
16 June - 17 June
New Downtown Luxury Townhouse in Bourbon Country

A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (128 reviews)
"Room Was clean -great location -had everything we needed. Would stay again on future trips "
United States
Cheryl B.
The price is AU$232
includes taxes & fees
17 June - 18 June
A Room Off Broadway, a prime downtown hideaway
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

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$232 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?

Hot Tub- Sleeps 8- Bourbon Trail- Historic Home: This holiday home rental outside of Boston offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.