Boston Vacation Rentals

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Our top choices for Boston vacation rentals

3.0 star property
10.0 out of 10, Exceptional, (4)
"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
$248 nightly
The price is $265
Dec 30 - Dec 31
Total with taxes and fees
Vine Grove Home w/ Deck, 4 Mi to Saunders Springs!
9.6 out of 10, Exceptional, (5)
"The property is very cozy, quiet, and comfortable! All the details were well thought out and I appreciated the informative labels, such as on the AC. Stayed in the queen bed which was super comfortable as well. Only suggestion would be to add directions on how to find it. I came in after dark and had a difficult time figuring out where it was after Google maps incorrectly sent me to an apartment building nearby. A unit number marking on the exterior would be useful, as I only realized I was in...
United States
Michael
$98 nightly
The price is $104
Jan 13 - Jan 14, 2026
Total with taxes and fees
Cozy Bourbon Trail Loft suite in charming Loretto
10.0 out of 10, Exceptional, (114)
"Unique, comfortable , cozy cabin, well equipped kitchen and bath . Communication with host excellent. Enjoyed our stay. "
United States
Linda
$150 nightly
The price is $165
Dec 30 - Dec 31
Total with taxes and fees
One of a kind cabin in the woods. Quiet and private but close to everything.
2.0 star property
10.0 out of 10, Exceptional, (28)
"This was a great little gem!! Plenty of room, had snacks, coffee, shampoo & soap. Definitely will stay again!!! "
United States
Joyce
$120 nightly
The price is $129
Jan 3 - Jan 4, 2026
Total with taxes and fees
Modern 2 Bed Suite on Bourbon Trail
9.8 out of 10, Exceptional, (12)
"Property is well maintained and the home owner was more than accommodating. "
United States
jeshaaiah
$157 nightly
The price is $173
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming 2-bedroom townhome with High Speed wifi and smart TV’s in Radcliff

Apartment in Elizabethtown

On The Square!
9.0 out of 10, Wonderful, (19)
"Everything was perfect. Would defiantly stay here again! "
United States
Wendy T.
$132 nightly
The price is $145
Dec 30 - Dec 31
Total with taxes and fees
On The Square!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot. Owners made everything easy. Super clean and welcoming home. Will stay again for next trip"
United States
Matthew M.
$386 nightly
The price is $425
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious, Pristine Home w/ Firepit, Bourbon Lounge
9.6 out of 10, Exceptional, (23)
"Great stay. Very clean and has everything you need. "
United States
Jeff
$129 nightly
The price is $138
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Rustic Suite on Bourbon Trail
9.8 out of 10, Exceptional, (51)
"Quiet, peaceful place to rest. Perfect for a weekend getaway"
United States
Ryan D.
$283 nightly
The price is $311
Dec 30 - Dec 31
Total with taxes and fees
Kentucky Sunrise 18- Greet the Sun As it Rises
10.0 out of 10, Exceptional, (16)
"Host was great to communicate with. Very nice little space "
United States
Travis R.
$172 nightly
The price is $184
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy cottage in charming New Hope with AC, WiFi
10.0 out of 10, Exceptional, (2)
"Awesome place!"
United States
Scott B.
$237 nightly
The price is $254
Dec 30 - Dec 31
Total with taxes and fees
Charming 2-bedroom cottage in peaceful Magnolia with WiFi, 30 acre private lake
10.0 out of 10, Exceptional, (16)
"Close to everything and owners are easy to contact."
United States
Sherry
$270 nightly
The price is $298
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fun 2 BdRm Apt in the Bourbon Capital with Pool Table, PAC-Man & More!
10.0 out of 10, Exceptional, (62)
"Great place to stay while doing a Bourbon Tour!!"
United States
PATRICIA
$263 nightly
The price is $290
Dec 31 - Jan 1, 2026
Total with taxes and fees
New Hope Bourbon Stop- historic home, peaceful spot in heart of Bourbon country
9.4 out of 10, Exceptional, (20)
"Great place good accommodation "
United States
Ryan D.
$278 nightly
The price is $306
Dec 30 - Dec 31
Total with taxes and fees
Angels Envy 29 - A relaxing place by the lake!
10.0 out of 10, Exceptional, (48)
"Clean comfortable quiet home in a lovely neighborhood with open space behind the house made for a lovely stay!!"
United States
Anonymous traveler
$316 nightly
The price is $348
Jan 11 - Jan 12, 2026
Total with taxes and fees
Bluegrass & Bourbon - a Peaceful Retreat & Hangout
10.0 out of 10, Exceptional, (21)
"Super cute & cozy cabin! It definitely felt like home away from home. Would definitely book again if we end up back in the area."
United States
Cayley S.
$155 nightly
The price is $166
Dec 30 - Dec 31
Total with taxes and fees
Nice log cabin home in the heart of bourbon country. Pet friendly.
2.0 star property
10.0 out of 10, Exceptional, (12)
"Great location, vey quiet and close to all the distilleries"
United States
Patrick D.
$439 nightly
The price is $470
Dec 30 - Dec 31
Total with taxes and fees
Bourbon Trail Oasis at Boone Farm - Private & Peaceful
9.0 out of 10, Wonderful, (14)
"Very clean and prefect location. Thank you A"
United States
Eric L.
$170 nightly
The price is $187
Dec 31 - Jan 1, 2026
Total with taxes and fees
Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown
2.0 star property
$140 nightly
The price is $154
Dec 31 - Jan 1, 2026
Total with taxes and fees
The E-town Retreat 2-bedroom townhome in beautiful Elizabethtown
10.0 out of 10, Exceptional, (54)
"Phenomenal location and amazingly beautiful on the inside. Walking distance to great food and fun. We love this place and couldn’t recommend it enough. Host was very responsive. 10/10 will stay here again"
United States
Joshua R.
$254 nightly
The price is $280
Jan 4 - Jan 5, 2026
Total with taxes and fees
New Downtown Luxury Townhouse in Bourbon Country
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

Everything you need to know about Boston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Boston vacation 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 low season months. For more hustle and bustle, you may prefer to visit Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston vacation 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 vacation.

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 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?

Ron & Orline's Home, park at the door & use our EV 50 amp charger: This vacation home near Boston offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games 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.