Boston Holiday Rentals

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Our top choices for Boston holiday rentals

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 AU$371
includes taxes & fees
28 Apr - 29 Apr
Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!

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$237
includes taxes & fees
28 Apr - 29 Apr
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

The E-town Retreat 2-bedroom townhome in beautiful Elizabethtown

The E-town Retreat 2-bedroom townhome in beautiful Elizabethtown
Elizabethtown
10.0 out of 10, Exceptional, (3 reviews)
"Nice place"
United States
Natalie G.
The price is AU$245
includes taxes & fees
28 Apr - 29 Apr
The E-town Retreat 2-bedroom townhome in beautiful Elizabethtown

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, (115 reviews)
"Great stay. "
United States
Royce
The price is AU$321
includes taxes & fees
28 Apr - 29 Apr
One of a kind cabin in the woods. Quiet and private but close to everything.

Cozy Bourbon Trail Loft suite in Loretto

Cozy Bourbon Trail Loft suite in Loretto
Loretto
9.8 out of 10, Exceptional, (7 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$215
includes taxes & fees
29 Apr - 30 Apr
Cozy Bourbon Trail Loft suite in Loretto

The Rustic Suite on Bourbon Trail

The Rustic Suite on Bourbon Trail
Loretto
9.6 out of 10, Exceptional, (28 reviews)
"This is a great place. Very comfortable and perfect location next to Makers Mark. Clean, nice amenities, and great communication. Highly recommend. "
United States
Sharon M.
The price is AU$213
includes taxes & fees
3 May - 4 May
The Rustic Suite on Bourbon Trail

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$357
includes taxes & fees
28 Apr - 29 Apr
Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake

Just 10 minutes from town -We're more than just a place to stay!

Just 10 minutes from town -We're more than just a place to stay!
Elizabethtown
9.4 out of 10, Exceptional, (21 reviews)
"Clean and comfortable. Really pretty country"
United States
Deborah B.
The price is AU$263
includes taxes & fees
29 Apr - 30 Apr
Just 10 minutes from town -We're more than just a place to stay!

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

New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country
New Hope
10.0 out of 10, Exceptional, (66 reviews)
"Great location, close to many bourbon stops.Would definitely stay again."
United States
Matthew M.
The price is AU$414
includes taxes & fees
28 Apr - 29 Apr
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country

New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (56 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$393
includes taxes & fees
6 May - 7 May
New Downtown Luxury Townhouse in Bourbon Country

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, (23 reviews)
"Such a beautiful place to stay!! "
United States
Gracie T.
The price is AU$476
includes taxes & fees
28 Apr - 29 Apr
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!

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 AU$201
includes taxes & fees
11 May - 12 May
Modern 2 Bed Suite on Bourbon Trail

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 AU$226
includes taxes & fees
29 Apr - 30 Apr
On The Square!

Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Bourbon Trail Oasis at Boone Farm - Private & Peaceful
Springfield
10.0 out of 10, Exceptional, (13 reviews)
"Great place for a large group."
United States
MATT 무용 B.
The price is AU$345
includes taxes & fees
4 May - 5 May
Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Country Clean Cozy

Country Clean Cozy
Elizabethtown
9.8 out of 10, Exceptional, (44 reviews)
"Great communication and instructions. House was perfect for our needs and location."
United States
Lynne Y.
The price is AU$458
includes taxes & fees
28 Apr - 29 Apr
Country Clean Cozy

Bluegrass & Bourbon - a Peaceful Retreat & Hangout

Bluegrass & Bourbon - a Peaceful Retreat & Hangout
Bardstown
10.0 out of 10, Exceptional, (54 reviews)
"Wonderful home, great location, looking forward to our next stay!"
United States
Cathy C.
The price is AU$540
includes taxes & fees
5 May - 6 May
Bluegrass & Bourbon - a Peaceful Retreat & Hangout

A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (125 reviews)
"Great location, clean room & a responsive host"
United States
Kerry M.
The price is AU$211
includes taxes & fees
3 May - 4 May
A Room Off Broadway, a prime downtown hideaway

Stay in a historic Early 1800s Guest House!

Stay in a historic Early 1800s Guest House!
Bardstown
9.8 out of 10, Exceptional, (122 reviews)
"House was clean, warm and charming. Walk to everythingPerfect stay !!!"
United States
Hoyt F.
The price is AU$267
includes taxes & fees
29 Apr - 30 Apr
Stay in a historic Early 1800s Guest House!

Love's Touch at R Applegate Family Farm

Love's Touch at R Applegate Family Farm
West Point
10.0 out of 10, Exceptional, (16 reviews)
"This place was beautiful and was the perfect place to stay while attending a music festival!"
United States
Kaylin L.
The price is AU$348
includes taxes & fees
4 May - 5 May
Love's Touch at R Applegate Family Farm

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, (3 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 AU$351
includes taxes & fees
11 May - 12 May
Bourbon Oak Hideaway 1 - Charming Studio Apartment on the Bourbon Trail -
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$211 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 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.