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
Stay at this vacation home in Brattleboro. Enjoy free WiFi, a garden, and patios. Popular attractions Sweet Pond State Park and Leyden State Forest are located ...
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
Stay at this vacation home in Shelburne Falls. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Bald Mountain Pottery and Salmon Falls ...
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
Stay at this vacation home in Jamaica. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Hot Glass Works and Ball Mountain State ...
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
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Mount Snow and Heavy Metal Ski ...
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cozy retreat near slopes

Cozy retreat near slopes

Dover
Stay at this vacation home in West Dover. Enjoy a sauna and an indoor pool. Popular attractions Mount Snow and Discovery Shuttle Ski Lift are located ...
Cozy retreat near slopes
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Book a stay at this family-friendly vacation home in Jacksonville. Enjoy a fitness center, a pool table, and cable/satellite TV service. Popular attractions ...
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
Stay at this vacation home in Wardsboro. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Stratton Mountain Resort and Margie's Muse Handweaving ...
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
Stay at this vacation home in Wilmington. Enjoy tennis courts, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Mount Snow and The ...
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
Book a stay at this family-friendly vacation home in West Dover. Enjoy a pool table, patios, and cable/satellite TV service. Our guests praise the property condition ...
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
Book a stay at this family-friendly vacation home in Jacksonville. Enjoy a fitness center, a pool table, and cable/satellite TV service. Popular attractions ...
GAMERS HAVEN, River Wine Inn!
Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville
Book a stay at this family-friendly cabin in Jacksonville. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Honora Winery and Jacksonville ...
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
Stay at this cabin in Jacksonville. Enjoy free WiFi, 2 outdoor pickleball courts, and a garden. Popular attractions H.O. Cook State Forest and West Branch Wildlife ...
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
Stay at this vacation home in Jacksonville. Enjoy a garden, a pool table, and patios. Popular attractions Jacksonville Pond and Honora Winery are located ...
Bright three-level home with water views, jetted tub, firepit, and pool table
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See all available properties in Jacksonville
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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.