Book Holiday Homes in Jacksonville

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Featured Holiday Homes in Jacksonville

The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A River Retreat
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Located in Jamaica, this vacation home is within a 5-minute drive of West River and Green Mountain National Forest.
Potter's Place | House in Jamaica with mountain views
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Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Wardsboro
Located in Wardsboro, this vacation home is in the mountains, within a 15-minute drive of Green Mountain National Forest and Wardsboro Public Library.
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!
Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington
Located in Wilmington, this vacation home is a 1-minute drive from Green Mountain National Forest and 7 minutes from North Branch Deerfield River.
Wilmington Vacation Rental Near Hiking and Skiing!
Mountain-view home near the slopes with at-home entertainment - dog-friendly

Mountain-view home near the slopes with at-home entertainment - dog-friendly

West Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Mountain-view home near the slopes with at-home entertainment - dog-friendly
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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.

Jacksonville 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 Jacksonville vacation homes are the perfect way for you to wing it.

Holiday houses in Jacksonville 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 Jacksonville 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 Jacksonville adventures, obvs.

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

Jacksonville Holiday Homes essential information

Accommodation
463 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Jelly Mill-A River Retreat, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Potter's Place | House in Jamaica with mountain views, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!, Wilmington Vacation Rental Near Hiking and Skiing!, Mountain-view home near the slopes with at-home entertainment - dog-friendly

Top trending hotels in Jacksonville

GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville
Located in Jacksonville, this cabin is a 5-minute drive from Honora Winery and 6 minutes from Jacksonville Pond.
Jacksonville Cabin w/ Wraparound Deck & Views
This is it!  Fabulous Vermont Cabin w/ 25 Acres to Explore!  Spectacular Views!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Halifax
Located in Jacksonville, this cabin is in the mountains, within a 15-minute drive of Jacksonville Pond and Harriman Reservoir.
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
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Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table

Jacksonville
Located in Jacksonville, this vacation home is on a lake, a 1-minute drive from Jacksonville Pond and 7 minutes from Honora Winery.
Bright three-level home with water views, jetted tub, firepit, and pool table
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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.