Boston Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Boston

Property grounds
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
10.0 out of 10, Exceptional, (178)
"A+++"
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Interior
Beautiful apartment in the heart of downtown Bardstown, KY
9.8 out of 10, Exceptional, (98)
"Perfect for a getaway. Great location for visiting many distilleries."
The price is NZ$358
per night
23 Jun - 24 Jun
Beautiful apartment in the heart of downtown Bardstown, KY
Property grounds
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
9.4 out of 10, Exceptional, (22)
"Yearly my wife and I get away just to enjoy our time together. This is the second year in a row we stayed at this location and we are planning on next year already. The cabin is so relaxing and the host is outstanding in communicating with us before our arrival. This is the place to be. Thank you for an enjoyable time."
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Apartment Downtown Bardstown<br>The PACK
10.0 out of 10, Exceptional, (29)
"Great location."
The price is NZ$439
per night
2 Jun - 3 Jun
Apartment Downtown Bardstown<br>The PACK
Exterior
Stay in a historic Early 1800s Guest House!
10.0 out of 10, Exceptional, (69)
"Enjoyable"
The price is NZ$335
per night
16 Jun - 17 Jun
Stay in a historic Early 1800s Guest House!
Interior
Kentucky House: 22-acre Property on Bourbon Trail
3.0 star property
Kentucky House: 22-acre Property on Bourbon Trail
Exterior
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 NZ$564
per night
10 Jun - 11 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 NZ$586
per night
29 May - 30 May
Conveniently located NEW Construction Mins to Ft. Knox, Blue Oval, Sportspark!
Interior
Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY
10.0 out of 10, Exceptional, (165)
"We enjoyed our 2 night stay in the heart of Bardstown. Conveniently located within walking distance to shops, restaurants, and a brewery. The place was very clean and had everything we needed. It was very nice to have a washer and dryer so we could do our laundry prior to returning home. We would definitely stay here again."
The price is NZ$448
per night
2 Jun - 3 Jun
Beautiful Decorated Apartment located in the heart of Downtown Bardstown, KY
Smart TV, DVD player, books
Family Wooded Retreat- Cottage 41
9.0 out of 10, Wonderful, (4)
"The basics on the property were as expected. The snacks were a nice touch and the basics for the property were fine. The TV only had Roku, so any network TV, such as watching the World Series at night, couldn't be done. I've stayed at other VRBOs and they were upfront about the TV channels access. Letting the renters know upfront on the property summary that the TV is only Roku should be done. The property manual on-site is way out of date and held in a broken spiral notebook. It contains...
Family Wooded Retreat- Cottage 41
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
Exterior
A Room Off Broadway, a prime downtown hideaway
10.0 out of 10, Exceptional, (49)
"Great place! Clean and easy to check in/out"
The price is NZ$278
per night
23 Jun - 24 Jun
A Room Off Broadway, a prime downtown hideaway
Fridge, microwave, oven, stovetop
BOOK NOW 4 LOUDER THAN LIFE!Bourbon Trail/Parks/Easy access/Dwntown/Pool/Firepit
10.0 out of 10, Exceptional, (67)
"We had a great time. The host was amazing and was very easy to get ahold of if we had any questions. Her home was beautiful and clean. I highly recommend staying here."
BOOK NOW 4 LOUDER THAN LIFE!Bourbon Trail/Parks/Easy access/Dwntown/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
Fridge, microwave, oven, stovetop
NEW GAME ROOM! Porch Sitting' 4 bed/2 bath; Bourbon Trail, Close to downtown.
10.0 out of 10, Exceptional, (24)
"What a great location, so close to many bourbon distilleries, restaurants & golf course. Many options which it was hard to choose the basement bar/games or sit on the front porch. It was a beautiful weekend and we chose the front porch. Great place to gather after a busy day tasting & tours. Thank you so much for sharing your place!"
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*
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 NZ$418
per night
3 Jun - 4 Jun
Ron & Orline's Home, park at the door & use our EV 50 amp charger
Fridge, microwave, oven, stovetop
Time To Relax, 5 BR, 2 Kings, 4 Queens, 3 Baths
10.0 out of 10, Exceptional, (1)
"I planned a weekend trip with my family to visit Louisville. This house was very nice. The host was excellent. The house was better than I expected. The host had all of the essential items you need. I will pick this home again if I’m ever in the Louisville area."
Time To Relax, 5 BR, 2 Kings, 4 Queens, 3 Baths
Outdoor dining
25% off June! Classic Kentucky Farm to host your Bluegrass Bourbon Adventure
10.0 out of 10, Exceptional, (26)
"We wish we had planned to stay longer! The house and the property is ideal! We very much enjoyed the outdoor seating and fire pit. The bedrooms were all well appointed and very comfortable. We would definitely plan to stay here again if we travel back to the area."
25% off June! Classic Kentucky Farm to host your Bluegrass Bourbon Adventure
Exterior
The Barefoot Cottage 53. Pet friendly with fee, NEW HOT TUB
10.0 out of 10, Exceptional, (31)
"Loved it. It was a perfect setup for our family getaway and spending a weekend with my brother who is in a wheeelchair. Love that the ramp up to the door was ada compliant…. Only complaint was that the doorways was too small to accommodate his wheelchair but it all worked out :) "
The Barefoot Cottage 53. Pet friendly with fee, NEW HOT TUB
Don't see what you're looking for?
See all available properties in Boston
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

Lobby
Gold Vault Inn
2.5 star property
8.2 out of 10, Very good, (753)
"Clean & convenient, place is dated but has been maintained. I have paid more and got less good place to stay for the price. "
The price is NZ$151
per night
29 May - 30 May
Gold Vault Inn
Pillow-top beds, desk, laptop workspace, blackout curtains
Distill-Inn
2.5 star property
9.0 out of 10, Wonderful, (632)
"The hotel was very clean and comfortable, the staff was very friendly and helpful. "
The price is NZ$195
per night
29 May - 30 May
Distill-Inn
Suite (2 Queen Beds & 1 Sofa Bed)
Ramada by Wyndham Elizabethtown
2.5 star property
7.6 out of 10, Good, (1000)
"Pleasantly surprised. Although it very talkative or friendly, the front desk agent was professional and quick. The hallways were spotless and the room was comfortable and clean. The bathtub could use a good scrubbing down. Kinda grimey. Breakfast was decent. I will gladly return. "
The price is NZ$203
per night
2 Jun - 3 Jun
Ramada by Wyndham Elizabethtown
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Boston holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Boston. 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 Boston. 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 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 holiday 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 Boston short-term rentals, that won’t be hard to do.

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 Boston is in the city centre, and equipped with air conditioning and free WiFi 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 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