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Featured Holiday Homes in Jacksonville

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Wardsboro
Stay at this vacation home in Wardsboro. Enjoy patios, an in-room coffeemaker, and a spa tub. Popular attractions Margie's Muse Handweaving & Gallery and Hot ...
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Primely Located Dover Escape < 1 Mi to Mt Snow!

Primely Located Dover Escape < 1 Mi to Mt Snow!

Dover
Stay at this vacation home in West Dover. Enjoy patios, Netflix, and an in-room coffeemaker. Popular attractions Mount Snow and Discovery Shuttle Ski Lift are ...
Primely Located Dover Escape < 1 Mi to Mt Snow!
Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Dover
Stay at this vacation home in East Dover. Enjoy an in-room coffeemaker. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
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Cozy Cabin Between Stratton Resort & Mount Snow

Cozy Cabin Between Stratton Resort & Mount Snow

Stratton
Stay at this vacation home in West Wardsboro. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Stratton Mountain Resort and Mount Snow ...
Cozy Cabin Between Stratton Resort & Mount Snow
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro
Book a stay at this golf vacation home in Wardsboro. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Stratton Mountain Resort and Margie's ...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Dover
Book a stay at this family-friendly vacation home in West Dover. Enjoy private pools, a sauna, and a garden. Popular attractions Mount Snow and Mount Snow Golf ...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
Stay at this vacation home in Whitingham. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Harriman Reservoir and The Ledge are located ...
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

West Dover Vermont
Stay at this vacation home in West Dover. Enjoy free WiFi, a sauna, and patios. Popular attractions Mount Snow and Discovery Shuttle Ski Lift are located ...
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Beautiful 4 Bedroom Townhome Minutes from Mt Snow

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

West Dover
Stay at this vacation home in West Dover. Enjoy free WiFi, a sauna, and patios. Popular attractions Mount Snow and Nitro Express Ski Lift are located ...
Beautiful 4 Bedroom Townhome Minutes from Mt Snow
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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
389 Holiday Homes
Lowest Price
NZ$191
Highest Price
NZ$336
Popular accommodation
Dog-friendly chalet cabin with valley view, deck, and private hot tub, Primely Located Dover Escape < 1 Mi to Mt Snow!, Fabulous Mountain Top Retreat - 10 minutes from mount snow!, Cozy Cabin Between Stratton Resort & Mount Snow, Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms, SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW! , Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16, Beautiful 4 Bedroom Townhome Minutes from Mt Snow

Top trending hotels in Jacksonville

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
Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$229 per night from 6 Jan to 7 Jan
NZ$229
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Hotel Downstreet
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
The price is NZ$336 per night from 5 Jan to 6 Jan
NZ$336
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Mountaineer Inn
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Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is NZ$191 per night from 1 Jan to 2 Jan
NZ$191
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
Colonial Motel And Spa
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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.