Boston Vacation Rentals

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Our top choices for Boston vacation rentals

Spacious, Pristine Home w/ Firepit, Bourbon Lounge

Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Bardstown
10.0 out of 10, Exceptional, (4 reviews)
"Great stay! And great location! Very helpful and responsive hosts! "
United States
Kelsey T.
The price is CA $238
CA $562 total
includes taxes & fees
Apr 13 - Apr 14
Spacious, Pristine Home w/ Firepit, Bourbon Lounge

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 CA $136
CA $369 total
includes taxes & fees
Mar 31 - Apr 1
Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!

NEW “Bourbon on the Square” Downtown Rustic Loft

NEW “Bourbon on the Square” Downtown Rustic Loft
Elizabethtown
10.0 out of 10, Exceptional, (22 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 CA $169
CA $318 total
includes taxes & fees
Apr 1 - Apr 2
NEW “Bourbon on the Square” Downtown Rustic Loft

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB
Taylorsville
9.8 out of 10, Exceptional, (24 reviews)
"Very nice house, new hot tub in the resort it was located in was very nice"
United States
Mike O.
The price is CA $260
CA $561 total
includes taxes & fees
Mar 31 - Apr 1
Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Bluegrass & Bourbon - a Peaceful Retreat & Hangout

Bluegrass & Bourbon - a Peaceful Retreat & Hangout
Bardstown
10.0 out of 10, Exceptional, (50 reviews)
"Perfect for our stay. "
United States
Ranee T.
The price is CA $176
CA $540 total
includes taxes & fees
Mar 31 - Apr 1
Bluegrass & Bourbon - a Peaceful Retreat & Hangout

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 CA $114
CA $195 total
includes taxes & fees
Mar 31 - Apr 1
Modern 2 Bed Suite on Bourbon Trail

A Bourbon Connoisseur's dream is where you will find Rolling Fork Farm

A Bourbon Connoisseur's dream is where you will find Rolling Fork Farm
Campbellsville
10.0 out of 10, Exceptional, (15 reviews)
"This cabin was awesome, and had all the amenities you need!"
United States
Matt C.
The price is CA $452
CA $921 total
includes taxes & fees
Mar 31 - Apr 1
A Bourbon Connoisseur's dream is where you will find Rolling Fork Farm

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, (114 reviews)
"Everything here was very well done. A perfect place for a couples get away. Super clean and really liked the layout.This will be our go-to when visiting Bardstown!"
United States
Rick W.
The price is CA $199
CA $317 total
includes taxes & fees
Apr 6 - Apr 7
One of a kind cabin in the woods. Quiet and private but close to everything.

Cozy KY Escape with Hot Tub near the Bourbon Trail

Cozy KY Escape with Hot Tub near the Bourbon Trail
Taylorsville
10.0 out of 10, Exceptional, (106 reviews)
"The cottage is very clean and comfortable. I stayed with a friend and we were both impressed by how comfortable the beds are. The area the cottage is in is very pretty. I didn't stay long because I was in and out for a wedding, but I would definitely book this cottage again."
United States
Rachel I.
The price is CA $263
CA $487 total
includes taxes & fees
Apr 4 - Apr 5
Cozy KY Escape with Hot Tub near the Bourbon Trail

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, (65 reviews)
"Great location, close to many bourbon stops.Would definitely stay again."
United States
Matthew M.
The price is CA $158
CA $406 total
includes taxes & fees
Mar 31 - Apr 1
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country

Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck

Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck
Springfield
9.8 out of 10, Exceptional, (17 reviews)
"Great home and layout in the peaceful countryside!"
United States
John P.
The price is CA $250
CA $610 total
includes taxes & fees
Apr 3 - Apr 4
Scenic Getaway near Bardstown & Bourbon Trail - Pet Friendly, Game Room, Deck

Peaceful home with a close proximity to downtown, sports park, and more

Peaceful home with a close proximity to downtown, sports park, and more
Elizabethtown
10.0 out of 10, Exceptional, (6 reviews)
"Clean and comfortable!"
United States
Teffany M.
The price is CA $313
CA $657 total
includes taxes & fees
Mar 31 - Apr 1
Peaceful home with a close proximity to downtown, sports park, and more

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 CA $131
CA $221 total
includes taxes & fees
Apr 5 - Apr 6
On The Square!

New Downtown Luxury Townhouse in Bourbon Country

New Downtown Luxury Townhouse in Bourbon Country
Elizabethtown
10.0 out of 10, Exceptional, (54 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 CA $186
CA $392 total
includes taxes & fees
Apr 1 - Apr 2
New Downtown Luxury Townhouse in Bourbon Country

Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Bourbon Trail Oasis at Boone Farm - Private & Peaceful
Springfield
10.0 out of 10, Exceptional, (12 reviews)
"Great place for a large group."
United States
MATT 무용 B.
The price is CA $174
CA $338 total
includes taxes & fees
Mar 31 - Apr 1
Bourbon Trail Oasis at Boone Farm - Private & Peaceful

Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!

Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!
Bardstown
10.0 out of 10, Exceptional, (31 reviews)
"Great stay! Very spacious, clean, and near everything we wanted to go to."
United States
Brent F.
The price is CA $264
CA $741 total
includes taxes & fees
Mar 31 - Apr 1
Bourbon Blue - Bourbon Trail Getaway - 8 minutes from Downtown Bardstown!

🌾 The Farmwife’s Hideaway 🌾 Small-town comfort with farmhouse charm.

🌾 The Farmwife’s Hideaway 🌾 Small-town comfort with farmhouse charm.
Bardstown
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful home, comfortable beds, great location! "
United States
Amanda B.
The price is CA $225
CA $394 total
includes taxes & fees
Mar 31 - Apr 1
🌾 The Farmwife’s Hideaway 🌾 Small-town comfort with farmhouse charm.

The Derby House - Relaxing retreat before and after the excitement of the Derby!

The Derby House - Relaxing retreat before and after the excitement of the Derby!
Louisville
9.6 out of 10, Exceptional, (18 reviews)
"Nice clean and quiet place! Close to down town Louisville! "
United States
Joe C.
The price is CA $231
CA $538 total
includes taxes & fees
Mar 31 - Apr 1
The Derby House - Relaxing retreat before and after the excitement of the Derby!

Cozy Bourbon Trail Loft suite in charming Loretto

Cozy Bourbon Trail Loft suite in charming 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 CA $111
CA $192 total
includes taxes & fees
Mar 31 - Apr 1
Cozy Bourbon Trail Loft suite in charming Loretto

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, (14 reviews)
"Great place to stay"
United States
Benjamin P.
The price is CA $375
CA $899 total
includes taxes & fees
Mar 31 - Apr 1
Bourbon Country Cabin - Game Room, Fire Pit, and Hot Tub
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Boston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Boston?

Yes, we offer vacation rentals near popular attractions in Boston, or you can go with a secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Boston has to offer?

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65: This vacation home rental near Boston is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 larger area, you’ll find Jim Beam American Outpost and Spalding Hall.

What’s a vacation rental in Boston like?

A vacation rental is a private property you can stay in for a long or short time in Boston. Vacation rentals offer amenities 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 sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for families.