Boston Holiday Rentals

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Holiday Rentals in Boston

Cozy cottage in charming New Hope with AC, WiFi

10.0 out of 10, Exceptional, (12)
"Was a great place to relax and get away. Awesome drive to property. Loved it"
The price is NZ$320
includes taxes & fees
13 Oct - 14 Oct
Cozy cottage in charming New Hope with AC, WiFi

Charming 3-bedroom house with WiFi and AC in lovely Loretto

2.0 star property
10.0 out of 10, Exceptional, (11)
"The house was cute and very clean! The outdoor area was great! Host was super easy to communicate with."
Charming 3-bedroom house with WiFi and AC in lovely Loretto

Stunning view! Hot Tub, Privacy & Relaxation

2.0 star property
10.0 out of 10, Exceptional, (19)
"We loved staying at the Ridge. Beautiful views, beautiful cabin and comfortable beds. Hope to be back sometime."
Stunning view! Hot Tub, Privacy & Relaxation

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

10.0 out of 10, Exceptional, (225)
"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 NZ$489
includes taxes & fees
20 Oct - 21 Oct
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, (13)
"We were looking for an off the beaten path and we were lucky to have this home to came back to every night of our stay. We loved sitting on the porch swing enjoying out morning coffee and listening to the sounds of nature. Home was clean well equipped and overall just perfect. "
The price is NZ$290
includes taxes & fees
13 Oct - 14 Oct
Nice log cabin home in the heart of bourbon country. Pet friendly.

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

10.0 out of 10, Exceptional, (156)
"Great stay! Amazing people! "
The price is NZ$449
includes taxes & fees
13 Oct - 14 Oct
Ron & Orline's Home, park at the door & use our EV 50 amp charger

Stay in a historic Early 1800s Guest House!

9.8 out of 10, Exceptional, (110)
"Great location and cottage! We loved it!"
The price is NZ$353
includes taxes & fees
29 Oct - 30 Oct
Stay in a historic Early 1800s Guest House!

A Room Off Broadway, a prime downtown hideaway

10.0 out of 10, Exceptional, (104)
"Great space, clean and perfect size for the two of us (adults). Definitely recommend the property and the town"
The price is NZ$279
includes taxes & fees
29 Oct - 30 Oct
A Room Off Broadway, a prime downtown hideaway

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

10.0 out of 10, Exceptional, (101)
"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

Spacious 3-bedroom cabin in wonderful Coxs Creek with WiFi, AC

10.0 out of 10, Exceptional, (5)
"We enjoyed this property so much! Everything that we needed within pretty good proximity of the KY expo center which is where we traveled too daily. Thank you so much for the quick responses & hospitality. "
Spacious 3-bedroom cabin in wonderful Coxs Creek with WiFi, AC

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

10.0 out of 10, Exceptional, (59)
"Great place to stay while doing a Bourbon Tour!!"
The price is NZ$511
includes taxes & fees
13 Oct - 14 Oct
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country

Beautiful apartment in the heart of downtown Bardstown, KY

9.6 out of 10, Exceptional, (148)
"Great location right in the middle of the town of Bardstown. Lots of space and very comfortable - we'd definitely stay again!"
The price is NZ$406
includes taxes & fees
28 Oct - 29 Oct
Beautiful apartment in the heart of downtown Bardstown, KY

Apartment Downtown Bardstown<br>The PACK

9.8 out of 10, Exceptional, (62)
"It was the perfect place to stay if you’re looking to stop in Bardstown. Located in the center of town within walking distance to everything."
The price is NZ$432
includes taxes & fees
13 Oct - 14 Oct
Apartment Downtown Bardstown<br>The PACK

3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass

10.0 out of 10, Exceptional, (25)
"We stayed here during the derby and it was magical! "
3-bedroom cabin just 30 minutes from The Outlet Shoppes of the Bluegrass

Foster & 5th / 3 BDRM Downtown Historical Colonial

9.8 out of 10, Exceptional, (52)
"Our group of friends had a wonderful stay! This place has plenty of parking, outdoor space, plenty of places to hang out inside, great bathrooms and comfortable bedrooms! We were a group of 6 and could sit and talk as a group or find our own nook to hang out in easily. Great decor and amenities. You cannot beat the location if you want to walk downtown Bardstown! "
Foster & 5th / 3 BDRM Downtown Historical Colonial

Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi

10.0 out of 10, Exceptional, (55)
"The property is SO well kept and beautiful! There is so much history and attention to detail everywhere! We highly recommend "
Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi

Bourbon Country Cabin - Game Room, Fire Pit, and Hot Tub

10.0 out of 10, Exceptional, (2)
"Exactly as listed. The Traeger was incredible. While we have one at home we have never had one at an VRBO. Great meals with family in bourbon country is exactly what we needed. Our Barn Olympics in the game room on the last night really made this a special trip. We had a great time and will most certainly be back next year. If you want a high end VRBO for your group of family and friends to enjoy each others company on the bourbon trail then book this VRBO today and you won’t be disappointed!!"
The price is NZ$1,087
includes taxes & fees
13 Oct - 14 Oct
Bourbon Country Cabin - Game Room, Fire Pit, and Hot Tub

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

9.2 out of 10, Wonderful, (15)
"It was so great. Super clean and awesome location. We got to roam around and enjoy the property as well"
The price is NZ$323
includes taxes & fees
13 Oct - 14 Oct
Just 10 minutes from town -We're more than just a place to stay!

NEW Distiller's Dream - Bourbon Trail Country Fun - 12 min to Bardstown Square

10.0 out of 10, Exceptional, (7)
"Our family of 8 adults and two young grandchildren absolutely loved this property! The home is beautifully decorated, and the kitchen is both stunning and fully equipped with everything you could possibly need, and more.The barn was a fantastic bonus: a fun and safe place for our grandsons to burn off energy before bedtime, and a perfect spot for the adults to unwind and enjoy games together.From the moment we booked until checkout, Melissa was incredibly responsive and helpful. We couldn’t have...
The price is NZ$1,138
includes taxes & fees
14 Oct - 15 Oct
NEW Distiller's Dream - Bourbon Trail Country Fun - 12 min to Bardstown Square

Bourbon Oak Hideaway 2 offers a 2 bed 2.5 bath apartment in historic Bardstown.

9.6 out of 10, Exceptional, (5)
"We were happy with everything about this place! Thanks so much. "
The price is NZ$545
includes taxes & fees
13 Oct - 14 Oct
Bourbon Oak Hideaway 2 offers a 2 bed 2.5 bath apartment in historic Bardstown.
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 favorite 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 depends 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 NZ$279 per night. Entering your travel dates in the search wizard you might find 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?

Stay in a historic Early 1800s Guest House!: This holiday home rental outside of Boston is in the city centre, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, 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.