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, (8 reviews)
"Great stay! And great location! Very helpful and responsive hosts! "
United States
Kelsey T.
The price is CA $254
CA $580 total
includes taxes & fees
May 19 - May 20
Spacious, Pristine Home w/ Firepit, Bourbon Lounge

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)
"Nice location"
United States
Cindy C.
The price is CA $99
CA $230 total
includes taxes & fees
May 19 - May 20
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

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 CA $131
CA $328 total
includes taxes & fees
May 19 - May 20
The Elizabethtown Hideaway

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 CA $116
CA $197 total
includes taxes & fees
May 31 - Jun 1
Modern 2 Bed Suite on Bourbon Trail

The Rustic Suite on Bourbon Trail

The Rustic Suite on Bourbon Trail
Loretto
9.6 out of 10, Exceptional, (32 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 CA $129
CA $211 total
includes taxes & fees
May 31 - Jun 1
The Rustic Suite on Bourbon Trail

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 CA $126
CA $207 total
includes taxes & fees
May 30 - May 31
Cozy Bourbon Trail Loft suite in Loretto

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, (3 reviews)
"Nice place"
United States
Natalie G.
The price is CA $121
CA $246 total
includes taxes & fees
Jun 14 - Jun 15
The E-Town Retreat 2BR townhouse close to Downtown

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)
"The ranch and area are beautiful! It was perfect for myself. Only wish it was warmer so I could sit outside and take it all in! The Hosts were amazing, attentive, polite…something a lot of places lack. I will absolutely be back!"
United States
Mark E.
The price is CA $155
CA $257 total
includes taxes & fees
May 19 - May 20
Just 10 minutes from town -We're more than just a place to stay!

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 $135
CA $365 total
includes taxes & fees
Jun 10 - Jun 11
Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!

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 CA $136
CA $343 total
includes taxes & fees
May 19 - May 20
Bourbon Oak Hideaway 1 - Charming Studio Apartment on the 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 CA $130
CA $219 total
includes taxes & fees
May 20 - May 21
On The Square!

A Room Off Broadway, a prime downtown hideaway

A Room Off Broadway, a prime downtown hideaway
Bardstown
10.0 out of 10, Exceptional, (126 reviews)
"Great location, clean room & a responsive host"
United States
Kerry M.
The price is CA $124
CA $205 total
includes taxes & fees
Jun 1 - Jun 2
A Room Off Broadway, a prime downtown hideaway

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, (67 reviews)
"Great location, close to many bourbon stops.Would definitely stay again."
United States
Matthew M.
The price is CA $150
CA $397 total
includes taxes & fees
May 19 - May 20
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country

Stay downtown within walking distance of restaurants, shopping, and breweries!

Stay downtown within walking distance of restaurants, shopping, and breweries!
Bardstown
9.4 out of 10, Exceptional, (89 reviews)
"Great location! Place was clean, and beds were comfy !"
United States
colleen w.
The price is CA $161
CA $299 total
includes taxes & fees
May 19 - May 20
Stay downtown within walking distance of restaurants, shopping, and breweries!

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, (117 reviews)
"Great stay. "
United States
Royce
The price is CA $197
CA $317 total
includes taxes & fees
May 19 - May 20
One of a kind cabin in the woods. Quiet and private but close to everything.

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, (6 reviews)
The price is CA $162
CA $335 total
includes taxes & fees
May 25 - May 26
The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown

Cozy Getaway at Stone Horse

Cozy Getaway at Stone Horse
Bardstown
10.0 out of 10, Exceptional, (29 reviews)
"Great stay and Abbey is a great host!"
United States
Shannon D.
The price is CA $136
CA $385 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Getaway at Stone Horse

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 CA $186
CA $352 total
includes taxes & fees
May 19 - May 20
Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake

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, (41 reviews)
"Great place"
United States
T C B.
The price is CA $212
CA $511 total
includes taxes & fees
Jun 15 - Jun 16
Charming 4BR w/ Fire Pit + Next to Barton 1792

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 CA $155
CA $332 total
includes taxes & fees
May 19 - May 20
Be Our Guest! Create Unforgettable Memories in This Unique Family Getaway!
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?

Hot Tub- Sleeps 8- Bourbon Trail- Historic Home: This vacation home rental near 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 you can cook with friends or family. Make the most of the 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 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.