Holiday Rentals in Boston

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Holiday Rentals in Boston

Property grounds
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
10.0 out of 10, Exceptional, (173)
"We stayed at this property for 5 nights. Perfect size for the 3 of us. Hot tub was awesome. Everything was provided from trash bags to soaps and shampoos. The neighborhood was quiet. A great place to get a way from it all and explore Kentucky!!!"
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Interior
Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY
10.0 out of 10, Exceptional, (161)
"The apartment was very clean and well stocked with all of the needed necessities for our visit. Owner always responded quickly for any questions we had during the booking process and visit. Bardstown was very convenient for distillery visits, restaurants and shops. Great breakfast place beneath the apartment. Short drive to our final destination in downtown Louisville for the Derby. Highly recommend this property for an enjoyable stay in Bardstown."
The price is €263
includes taxes & fees
23 May - 24 May
Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY
Exterior
A Room Off Broadway, a prime downtown hideaway
10.0 out of 10, Exceptional, (48)
"This is beautiful property and Amelia is a great host. She has thought of everything and anything you might need during your stay. Water in the fridge, Keurig coffee, fruit, snack bars, etc.. I have already recommended this to my friends and if we ever go back to Bardstown we would definitely plan our trip around the availability of this property. Bardstown is great and their is great shopping, restaurants, a brew pub, and history. I highly recommend this property."
The price is €162
includes taxes & fees
21 May - 22 May
A Room Off Broadway, a prime downtown hideaway
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Exterior
Apartment Downtown Bardstown<br>The PACK
10.0 out of 10, Exceptional, (29)
"Great location."
The price is €256
includes taxes & fees
19 May - 20 May
Apartment Downtown Bardstown<br>The PACK
Outdoor dining
Open Derby Week! Classic Kentucky Farm to host your Bluegrass Bourbon Adventure
10.0 out of 10, Exceptional, (24)
"The property is gorgeous from inside out. Owner has put a lot of thought into making this place feel welcoming and unique. It exudes charm and relaxation. Perfect for a family or friend getaway."
Open Derby Week! Classic Kentucky Farm to host your Bluegrass Bourbon Adventure
Fridge, microwave, oven, stovetop
BOOK NOW FOR DERBY! Bourbon Trail/Parks Easy access to Downtown w/Pool/Firepit
10.0 out of 10, Exceptional, (64)
"We really enjoyed the stay and the property was great. We would definitely stay here again"
BOOK NOW FOR DERBY! Bourbon Trail/Parks Easy access to Downtown w/Pool/Firepit
Fridge, microwave, oven, stovetop
The Bourbon Charm Homestay. Bourbon Trail, PGA, Derby
10.0 out of 10, Exceptional, (5)
"We were up in Kentucky for 4 days, this house was our home away from home. The kids loved it and the beds are amazing! It's too bad we didn't have time to enjoy the fire pit, we would have loved that as well as the grill if we had another night to stay. They have already told me to we have to stay there again next year. It's 10 minutes from Kroger, James Beam Distillery and the Bernheim Forest and Makers Mark Distillery is not too far as well."
The Bourbon Charm Homestay. Bourbon Trail, PGA, Derby
Exterior
Stay in a historic Early 1800s Guest House!
10.0 out of 10, Exceptional, (68)
"Nice property, quiet neighborhood, easy walk to downtown."
The price is €194
includes taxes & fees
21 May - 22 May
Stay in a historic Early 1800s Guest House!
The Angels Share 4BR in Bardstown KY on Bourbon Trail
10.0 out of 10, Exceptional, (9)
"We planned this stay to take advantage of the Bourbon Trail. We were able to visit many distilleries due to their close proximity of this home! The home is beautifully decorated and the beds are comfortable. We took advantage of the outside gas grill and cooked some delicious steaks one night. Brickhouses are right next door which was a special treat to see. We will definitely stay here again!"
The price is €298
includes taxes & fees
3 Jun - 4 Jun
The Angels Share 4BR in Bardstown KY on Bourbon Trail
Terrace/patio
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!
10.0 out of 10, Exceptional, (4)
"This rental is exactly as listed. It is beautiful!! The owners were great to respond to all of our questions or needs in a timely manner! Plan to rent again if in the area in the future!!!"
The price is €342
includes taxes & fees
27 May - 28 May
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!
Interior
Cozy cabin surrounded by nature, w/2 fire pits. Super close to towns and parks.
10.0 out of 10, Exceptional, (4)
"Best stay ever in a home rental. Loved the property. Loved the home and set up. Loved the privacy. Had a great time. We'll be coming back. Told all our friends how great it was."
Cozy cabin surrounded by nature, w/2 fire pits. Super close to towns and parks.
Exterior
Ron & Orline's Home, park at the door & use our EV 50 amp charger
10.0 out of 10, Exceptional, (137)
"Amazing property and an outstanding host"
The price is €246
includes taxes & fees
21 May - 22 May
Ron & Orline's Home, park at the door & use our EV 50 amp charger
Fridge, microwave, oven, stovetop
NEW GAME ROOM! Porch Sitting' 4 bed/2 bath; Bourbon Trail, Close to downtown.
10.0 out of 10, Exceptional, (23)
"This was a great place for us to stay with our family of 7 (all adults) to attend the 150th Kentucky Derby. It had plenty of room and nice living room to hang out. The porch was awesome! We really enjoyed Bardstown."
NEW GAME ROOM! Porch Sitting' 4 bed/2 bath; Bourbon Trail, Close to downtown.
Fridge, microwave, oven, stovetop
Call Me Old Fashioned! *Heart of Bardstown Square*
10.0 out of 10, Exceptional, (30)
"We loved this property. It was perfect for us, three couples. It was a little rainy on our weekend so didn’t get a chance to walk into town but loved how close we were to everything."
Call Me Old Fashioned! *Heart of Bardstown Square*
Smart TV, fireplace, video games, table football
LogCabin-15 min Bardstown Pool
10.0 out of 10, Exceptional, (2)
"We had eleven family members together to celebrate our parent's anniversary. The house and grounds are gorgeous! The layout of the house is great for that many people. Lots of areas to gather and visit or play games. There were a couple hiccups that were addressed very quickly. We also found out they were probably due to lightning or power surge from tornado that had come through the day before our visit. So, we can hardly blame them for freak occurrences. Overall, we all had an amazing time. We...
LogCabin-15 min Bardstown Pool
Interior
Spacious Kentucky Home in the Heart of Derby and Bourbon Country
10.0 out of 10, Exceptional, (1)
"Our family had a great stay in Mount Washington for Thanksgiving. We had three generations in the house staying together, and it was perfect for what we all needed. Every bedroom except one has its own connected bathroom, which made showers and getting ready so easy. Amazingly, we never ran out of hot water! Big plus! The house has been completely renovated and everything is new and beautiful. The kitchen was perfectly stocked with everything we needed for cooking. The TVs were connected to...
Spacious Kentucky Home in the Heart of Derby and Bourbon Country
Fridge, microwave, oven, stovetop
Whiskey Business *Heart of Bardstown Square*
10.0 out of 10, Exceptional, (17)
"Beautiful home, very comfortable, walkable to town and easliy accessible to major roads. We had a very enjoyable vacation."
Whiskey Business *Heart of Bardstown Square*
Exterior
UPSCALE 1 STORY on BOURBON TRAI Many UPGRADES Beds 1 XL K/S 2 XL Singles & Q/S
10.0 out of 10, Exceptional, (54)
"The property is beautiful, clean, great location and stocked like no other VRBO we've ever stayed at! The owner is incredibly responsive and wonderful to work with. She gave us a ton of stuff and advice while in the area that was very helpful! If we ever get back to Bardstown, we will definitely book again!"
UPSCALE 1 STORY on BOURBON TRAI Many UPGRADES Beds 1 XL K/S 2 XL Singles & Q/S
Aerial view
Bourbon Estate™ at Meadow Creek
10.0 out of 10, Exceptional, (42)
"Overall our stay was great. It would be nice especially with drastic temperature changes if we could adjust the temp without calling for it to be changed. A working ice maker would also be an asset. The kitchen was very well stocked a real plus since we like to cook."
Bourbon Estate™ at Meadow Creek
Interior
Beautiful apartment in the heart of downtown Bardstown, KY
9.8 out of 10, Exceptional, (94)
"Really nice place, convenient to the historic downtown area."
The price is €215
includes taxes & fees
21 May - 22 May
Beautiful apartment in the heart of downtown Bardstown, KY
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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.

Other types of properties in Boston you may be interested in

Pillow-top beds, desk, laptop workspace, blackout curtains
Distill-Inn
2.5 star property
9.0 out of 10, Wonderful, (616)
"Stayed the night for a nearby concert. Friendly and helpful staff. Clean and comfortable room. Loved the bourbon theme. Would stay here again!"
The price is €121
includes taxes & fees
21 May - 22 May
Distill-Inn
Exterior
Best Western Louisville South / Shepherdsville
2.5 star property
8.4 out of 10, Very good, (530)
"The staff was very professional and eager to make my stay a success. The manager was extremely helpful and a pleasure to meet."
The price is €78
includes taxes & fees
14 Jun - 15 Jun
Best Western Louisville South / Shepherdsville
Lobby
Gold Vault Inn
2.5 star property
8.2 out of 10, Very good, (733)
"Feels like home, staff is very helpful and nice, ty Rachel Sue and Anthony my stay has been great. at the Gold Valut Inn"
The price is €86
includes taxes & fees
25 May - 26 May
Gold Vault Inn
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.

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, apart-hotels, 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 €162 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?

Couples Cozy Lake Cottage at Edgewater Resort 36: This holiday home rental outside Boston is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Heaven Hill Bourbon Heritage Center.

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.

Recent reviews of Boston properties
Expedia verified reviews

Gold Vault Inn

Gold Vault Inn

5/5 Excellent
"Feels like home, staff is very helpful and nice, ty Rachel Sue and Anthony my stay has been great. at the Gold Valut Inn"
A verified traveller stayed at Gold Vault Inn
Posted 21 hours ago
Gold Vault Inn