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Boston Holiday Rentals

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Our top choices for Boston holiday rentals

1. 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, (126 reviews)
"Great stay. "
United States
Royce
The price is AU$302
includes taxes & fees
3 Aug - 4 Aug
One of a kind cabin in the woods. Quiet and private but close to everything.

2. The E-Town Retreat 2BR townhouse close to Downtown

The E-Town Retreat 2BR townhouse close to Downtown
Elizabethtown
9.8 out of 10, Exceptional, (8 reviews)
"Nice place"
United States
Natalie G.
The price is AU$260
includes taxes & fees
2 Aug - 3 Aug
The E-Town Retreat 2BR townhouse close to Downtown

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

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (12 reviews)
"Great stay! And great location! Very helpful and responsive hosts! "
United States
Kelsey T.
The price is AU$571
includes taxes & fees
3 Aug - 4 Aug
Spacious, Pristine Home w/ Firepit, Bourbon Lounge

4. 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, (10 reviews)
"The home is quite comfortable and a nice, scenic property. There was very little road noise, providing an excellent night’s sleep. We would absolutely stay here again."
United States
Erin A.
The price is AU$359
includes taxes & fees
13 Aug - 14 Aug
Lovely 3-bedroom home near the Bourbon Trail, with a lake in a country setting

5. 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 price is AU$364
includes taxes & fees
26 Aug - 27 Aug
The Elizabethtown Hideaway

6. The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown

The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown
Bardstown
10.0 out of 10, Exceptional, (15 reviews)
"Cute place to stay in Bardstown!"
United States
Allison M.
The price is AU$328
includes taxes & fees
6 Aug - 7 Aug
The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown

7. On The Square!

On The Square!
Elizabethtown
9.0 out of 10, Wonderful, (27 reviews)
"Perfect little hidden gem! And walking distance to EVERYTHING!"
United States
Katie W.
The price is AU$232
includes taxes & fees
2 Aug - 3 Aug
On The Square!

8. New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (59 reviews)
"Return visit. Todd and Teresa are gracious hosts with an amazing property. We were able to enjoy the porch and rooftop this trip since the weather was cooperative. If we are back in the area, this property will be our first choice!"
United States
Tina C.
The price is AU$443
includes taxes & fees
11 Aug - 12 Aug
New Downtown Luxury Townhouse in Bourbon Country

9. A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (134 reviews)
"Amazing stay all the way around! Would definitely plan to stay here again. "
United States
Matt R.
The price is AU$250
includes taxes & fees
2 Aug - 3 Aug
A Room Off Broadway, a prime downtown hideaway

10. 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, (20 reviews)
"Wonderful home with a great host!"
United States
Megan H.
The price is AU$267
includes taxes & fees
2 Aug - 3 Aug
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

11. 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, (25 reviews)
"Such a beautiful place to stay!! "
United States
Gracie T.
The price is AU$484
includes taxes & fees
2 Aug - 3 Aug
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!

12. 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, (4 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$358
includes taxes & fees
2 Aug - 3 Aug
Bourbon Oak Hideaway 1 - Charming Studio Apartment on the Bourbon Trail -

13. Charming 4BR w/ Fire Pit + Next to Barton 1792

Charming 4BR w/ Fire Pit + Next to Barton 1792
Bardstown
10.0 out of 10, Exceptional, (44 reviews)
"Enjoyed the stay. The hosts were very helpful."
United States
Justin D.
The price is AU$470
includes taxes & fees
4 Aug - 5 Aug
Charming 4BR w/ Fire Pit + Next to Barton 1792

14. Bluegrass & Bourbon - a Peaceful Retreat & Hangout

Bluegrass & Bourbon - a Peaceful Retreat & Hangout
Bardstown
10.0 out of 10, Exceptional, (62 reviews)
"Wonderful home, great location, looking forward to our next stay!"
United States
Cathy C.
The price is AU$590
includes taxes & fees
11 Aug - 12 Aug
Bluegrass & Bourbon - a Peaceful Retreat & Hangout

15. “New” Elizabethtown Poplar Place!

“New” Elizabethtown Poplar Place!
Elizabethtown
10.0 out of 10, Exceptional, (33 reviews)
"Relatively quiet neighborhood with quick access to downtown. We loved the screened in porch and spent a lot of time out there!"
United States
MacKenzie S.
The price is AU$374
includes taxes & fees
2 Aug - 3 Aug
“New” Elizabethtown Poplar Place!

16. 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, (23 reviews)
"Great house, relaxing environment, would definitely stay again!"
United States
Dustin S.
The price is AU$967
includes taxes & fees
12 Aug - 13 Aug
Bourbon Country Cabin - Game Room, Fire Pit, and Hot Tub

17. 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)
"Great place. Highly recommend "
United States
Matthew W.
The price is AU$371
includes taxes & fees
3 Aug - 4 Aug
Ron & Orline's Home, park at the door & use our EV 50 amp charger

18. Stay in a historic Early 1800s Guest House!

Stay in a historic Early 1800s Guest House!
Bardstown
9.8 out of 10, Exceptional, (131 reviews)
"Such a great stay. Walking distance to everything! Highly recommend this adorable, quality place for your trip to Bardstown! "
United States
Jillian g.
The price is AU$275
includes taxes & fees
5 Aug - 6 Aug
Stay in a historic Early 1800s Guest House!

19. Old Maple House -touch of Canadian charm on Kentuckys Bourbon Trail. Circa 1901.

Old Maple House -touch of Canadian charm on Kentuckys Bourbon Trail. Circa 1901.
Elizabethtown
10.0 out of 10, Exceptional, (31 reviews)
"Charming house in great location. It truly had everything we needed for a comfortable and relaxing stay. Will definitely stay there again!"
United States
Terri T.
Old Maple House -touch of Canadian charm on Kentuckys Bourbon Trail. Circa 1901.

20. Lavish Rooftop Condo B with free ev charging for any vehicle

Lavish Rooftop Condo B with free ev charging for any vehicle
Elizabethtown
9.8 out of 10, Exceptional, (6 reviews)
"Clean condo with beautiful rooftop views and an easy walk to local restaurants. The host communicated quickly and was great to work with. Highly recommended!"
United States
Joel K.
The price is AU$438
includes taxes & fees
2 Aug - 3 Aug
Lavish Rooftop Condo B with free ev charging for any vehicle
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?

Missy’s unique stays: This holiday home rental outside of Boston is located in a rural location, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave. 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.