Book Holiday Homes in Boston

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Featured Holiday Homes in Boston

Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown

Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown

Elizabethtown
The price is AU$300 per night from 29 Dec to 30 Dec
AU$300
includes taxes & fees
29 Dec - 30 Dec
Located in Elizabethtown, this vacation home is within a 15-minute walk of The Town Mall Shopping Center and Towne Mall.
Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown
16 Mi to Louisville: Pet-Friendly Getaway!

16 Mi to Louisville: Pet-Friendly Getaway!

Shepherdsville
Located in Shepherdsville, this vacation home is a 4-minute drive from Bullitt County History Museum and 6 minutes from Paroquet Springs Conference Center.
16 Mi to Louisville: Pet-Friendly Getaway!
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Shepherdsville
The price is AU$716 per night from 5 Jan to 6 Jan
AU$716
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Shepherdsville, this vacation home is in a rural location, within a 10-minute drive of McNeely Lake Park and Maplehurst Golf Course.
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
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Stunning view! Hot Tub, Privacy & Relaxation

Stunning view! Hot Tub, Privacy & Relaxation

2 out of 5
Raywick
This vacation home is 13.8 mi (22.3 km) from Fresenius Medical Care and 14.3 mi (23 km) from Veterans Memorial Park.
Stunning view! Hot Tub, Privacy & Relaxation
Stylish & Modern Elizabethtown Retreat on Main St!

Stylish & Modern Elizabethtown Retreat on Main St!

Elizabethtown
With a stay at this vacation home in Elizabethtown, you'll be within a 5-minute walk of Brown Pusey House and The Cannonball.
Stylish & Modern Elizabethtown Retreat on Main St!
Horse Farm 4-bedroom house with AC and WiFi in Bourbon Country

Horse Farm 4-bedroom house with AC and WiFi in Bourbon Country

2 out of 5
Bardstown
Located in Bardstown, this vacation home is within a 10-minute drive of At Mary's and Shaq & Coco.
Horse Farm 4-bedroom house with AC and WiFi in Bourbon Country
Time To Relax, 5 BR,  2 Kings, 4 Queens, 3 Baths

Time To Relax, 5 BR, 2 Kings, 4 Queens, 3 Baths

Radcliff
Located in Radcliff, this vacation home is a 4-minute drive from Boundary Oak Distillery and 7 minutes from Saunders Springs Nature Preserve.
Time To Relax, 5 BR, 2 Kings, 4 Queens, 3 Baths
Couples Cozy Lake Cottage at Edgewater Resort 36

Couples Cozy Lake Cottage at Edgewater Resort 36

Taylorsville
Located in Taylorsville, this vacation home is on a lake, a 1-minute drive from Taylorsville Lake and 5 minutes from Taylorsville Lake State Park.
Couples Cozy Lake Cottage at Edgewater Resort 36
Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks

Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks

Bardstown
The price is AU$403 per night from 24 Dec to 25 Dec
AU$403
includes taxes & fees
24 Dec - 25 Dec
Located in Bardstown, this vacation home is within a 5-minute drive of At Mary's and Shaq & Coco.
Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks
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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.

Boston Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Boston vacation homes are the perfect way for you to wing it.

Holiday houses in Boston let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Boston in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Boston adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Boston with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Boston vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Boston Holiday Homes essential information

Accommodation
114 Holiday Homes
Lowest Price
AU$104
Highest Price
AU$716
Popular accommodation
Charming 2-bedroom townhome with AC, WiFi in nice Elizabethtown, 16 Mi to Louisville: Pet-Friendly Getaway!, Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!, Stunning view! Hot Tub, Privacy & Relaxation, Stylish & Modern Elizabethtown Retreat on Main St!, Horse Farm 4-bedroom house with AC and WiFi in Bourbon Country, Time To Relax, 5 BR, 2 Kings, 4 Queens, 3 Baths, Couples Cozy Lake Cottage at Edgewater Resort 36, Bourbon Royale, Home of Two Kings; putting green, downtown, free coffee & snacks

Top trending hotels in Boston

Wingfield Inn and Suites

Wingfield Inn and Suites

2 out of 5
1043 Executive Drive Hardin, Elizabethtown, KY
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 23 Jan to 24 Jan
AU$113
includes taxes & fees
23 Jan - 24 Jan 2025
When you stay at Wingfield Inn and Suites in Elizabethtown, you'll be near the airport, within a 5-minute drive of Schmidt Museum of Coca Cola Memorabilia and ...
Wingfield Inn and Suites
Distill-Inn

Distill-Inn

2.5 out of 5
984 Frost Ave, Bardstown, KY
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 24 Dec to 25 Dec
AU$168
includes taxes & fees
24 Dec - 25 Dec
When you stay at Distill-Inn in Bardstown, you'll be in the historical district, within a 5-minute drive of At Mary's and Shaq & Coco.
Distill-Inn
 Quality Inn & Suites Brooks Louisville South

Quality Inn & Suites Brooks Louisville South

3 out of 5
716 Brooks Hill Rd, Brooks, KY
Fully refundableReserve now, pay when you stay
The price is AU$111 per night from 12 Jan to 13 Jan
AU$111
includes taxes & fees
12 Jan - 13 Jan 2025
With a stay at Quality Inn & Suites Brooks Louisville South in Brooks (Hillview), you'll be within a 15-minute drive of Kentucky Exposition Center and Louisville ...
Quality Inn & Suites Brooks Louisville South
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Gold Vault Inn

Gold Vault Inn

2.5 out of 5
1225 N.Dixie Blvd, Radcliff, KY
Fully refundableReserve now, pay when you stay
The price is AU$104 per night from 3 Jan to 4 Jan
AU$104
includes taxes & fees
3 Jan - 4 Jan 2025
Located in Radcliff, Gold Vault Inn is within a 5-minute drive of Saunders Springs Nature Preserve and United States Bullion Depository.
Gold Vault Inn
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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.

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^Subject to availability and chosen travel dates.