Book Holiday Homes in Jacksonville

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Featured Holiday Homes in Jacksonville

FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain MA
Stay at this family-friendly holiday home in Colrain. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Arthur A. Smith Covered ...
Opens in a new windowFaLL Western Mass Getaway-Airhockey-Firepit
Amazing lake views & access,HotTub & sauna, quality game Rm.  190-5 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington VT
Stay at this family-friendly holiday home in Wilmington. Enjoy free Wi-Fi, a sauna and a garden. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowAmazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA

2 out of 5
Goshen MA
Stay at this holiday home in Goshen. Popular attractions Three Sisters Sanctuary and Swift River are located nearby.
Opens in a new windowExperience Three Sisters Sanctuary in Goshen, MA
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 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
Stay at this ski holiday home in West Dover. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mount Snow and Heavy Metal Ski Lift are located ...
Opens in a new window 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT
Stay at this family-friendly holiday home in Wilmington. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowBeautiful Custom Built Timber Frame Home, Sleeps 11
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

West Dover Vermont VT
Stay at this family-friendly holiday home in West Dover. Enjoy free Wi-Fi, a sauna and laundry facilities. Popular attractions Mount Snow and Discovery Shuttle ...
Opens in a new windowLuxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont MA
The price is NZ$731 per night from 23 Dec to 24 Dec
NZ$731
23 Dec - 24 Dec
includes taxes & fees
Stay at this holiday home in Charlemont. Enjoy laundry facilities and air conditioning. Popular attractions Charlemont Historical Society and Museum and Thunderbolt ...
Opens in a new windowRiverbend Berkshire East Basecamp - 3 bedrooms available
Spacious Riverfront Home 7 Minutes to Stratton!

Spacious Riverfront Home 7 Minutes to Stratton!

Jamaica VT
Stay at this family-friendly holiday home in Jamaica. Enjoy laundry facilities, cable/satellite TV service and an in-room coffee maker. Popular attractions Stratton ...
Opens in a new windowSpacious Riverfront Home 7 Minutes to Stratton!
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2 out of 5
Shelburne Falls MA
Stay at this holiday home in Shelburne Falls. Enjoy a garden, laundry facilities and cable/satellite TV service. Popular attractions Bald Mountain Pottery and ...
Opens in a new windowStylish new 2 bedroom property in enchanting Shelburne Falls Village.
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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
405 Holiday Homes
Lowest Price
NZ$243
Highest Price
NZ$731
Popular accommodation
FaLL Western Mass Getaway-Airhockey-Firepit, Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews, Experience Three Sisters Sanctuary in Goshen, MA, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base, Beautiful Custom Built Timber Frame Home, Sleeps 11, Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!, Riverbend Berkshire East Basecamp - 3 bedrooms available, Spacious Riverfront Home 7 Minutes to Stratton!, Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Top trending hotels in Jacksonville

The Engel House

The Engel House

3 out of 5
204 VT-112 Jacksonville VT
Stay at this B&B in Jacksonville. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Jacksonville Pond and Honora Winery are located ...
Opens in a new windowThe Engel House
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is NZ$243 per night from 20 Jan to 21 Jan
NZ$243
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
The price is NZ$637 per night from 23 Dec to 24 Dec
NZ$637
23 Dec - 24 Dec
includes taxes & fees
Stay at this spa resort in West Dover. Enjoy free Wi-Fi, free parking and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located ...
Opens in a new windowMount Snow Grand Summit Resort
Save an average of 15% on thousands of hotels when you're signed in
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
231 River Street North Adams MA
Fully refundableReserve now, pay when you stay
The price is NZ$318 per night from 20 Jan to 21 Jan
NZ$318
20 Jan - 21 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowThe Porches Inn at Mass MoCA
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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.