Boston Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Boston holiday rentals

Living area

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 HK$1,446
HK$3,304 total
includes taxes & fees
26 May - 27 May
Spacious, Pristine Home w/ Firepit, Bourbon Lounge
Fridge, microwave, oven, stovetop

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 HK$564
HK$1,312 total
includes taxes & fees
18 May - 19 May
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff
Interior

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 HK$744
HK$1,853 total
includes taxes & fees
18 May - 19 May
The Elizabethtown Hideaway
Property grounds

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 HK$662
HK$1,120 total
includes taxes & fees
28 May - 29 May
Modern 2 Bed Suite on Bourbon Trail
Terrace/patio

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 HK$736
HK$1,199 total
includes taxes & fees
31 May - 1 Jun
The Rustic Suite on Bourbon Trail
Interior

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 HK$719
HK$1,180 total
includes taxes & fees
30 May - 31 May
Cozy Bourbon Trail Loft suite in Loretto
TV

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 HK$689
HK$1,401 total
includes taxes & fees
14 Jun - 15 Jun
The E-Town Retreat 2BR townhouse close to Downtown
1 bedroom, iron/ironing board, WiFi, bed sheets

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 HK$881
HK$1,446 total
includes taxes & fees
18 May - 19 May
Just 10 minutes from town -We're more than just a place to stay!
Front of property

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 HK$767
HK$2,078 total
includes taxes & fees
10 Jun - 11 Jun
Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!
Interior

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 HK$854
HK$1,968 total
includes taxes & fees
30 May - 31 May
Bourbon Oak Hideaway 1 - Charming Studio Apartment on the Bourbon Trail -
Outdoor dining

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 HK$740
HK$1,248 total
includes taxes & fees
18 May - 19 May
On The Square!
Terrace/patio

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 HK$705
HK$1,165 total
includes taxes & fees
28 May - 29 May
A Room Off Broadway, a prime downtown hideaway
Dining

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 HK$853
HK$2,226 total
includes taxes & fees
18 May - 19 May
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country
TV, fireplace, books

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 HK$1,018
HK$1,770 total
includes taxes & fees
16 Jun - 17 Jun
Stay downtown within walking distance of restaurants, shopping, and breweries!
Exterior

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 HK$1,121
HK$1,779 total
includes taxes & fees
18 May - 19 May
One of a kind cabin in the woods. Quiet and private but close to everything.
2 bedrooms, WiFi, bed sheets

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 HK$958
HK$1,877 total
includes taxes & fees
10 Jun - 11 Jun
The Cottage - Wonderful 2-bedroom house with AC, WiFi in charming Bardstown
Fridge, microwave, oven, stovetop

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 HK$775
HK$2,158 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Getaway at Stone Horse
Exterior

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 HK$1,057
HK$1,979 total
includes taxes & fees
18 May - 19 May
Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake
Property grounds

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 HK$880
HK$2,480 total
includes taxes & fees
18 May - 19 May
Charming 4BR w/ Fire Pit + Next to Barton 1792
Interior

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 HK$881
HK$1,865 total
includes taxes & fees
18 May - 19 May
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

Red Roof Inn Radcliff - Fort Knox

Red Roof Inn Radcliff - Fort Knox

8/10 Good
"This property looked recently updated and everything was in very good condition (furniture, decor, etc), and was very pet friendly. I was really very surprised because it was very budget friendly pricing and so I expected it to be a bit run down. The stuff was friendly. There was an issue with my room because I booked a king size (at time of booking it said 3 available), but when I checked in at 2:30 I was told all they had available was 2 doubles. It was ok enough with me and the staff was friendly about it but it was not what I was expecting. Since the place was so nicely kept though, I over looked that minor detail. Overall, nice stay for a great price."
Janice 1-night trip
Posted 2 hours ago
Red Roof Inn Radcliff - Fort Knox

Find out more about Boston

Search for holiday rentals in Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in Boston using one of the methods below:

  • View our selection of featured holiday rentals in Boston
  • Use the map to find apartments and other holiday homes in the Boston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Boston while they last

Look no further and take a look at our great range of rental properties in Boston!

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.