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Jacksonville Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Jacksonville holiday rentals

A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

1. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.8 out of 10, Excellent, (6 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is AU$911
includes taxes & fees
12 Oct - 13 Oct
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A wooden interior with a kitchen, bar area, and dining space.

2. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (6 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is AU$387
includes taxes & fees
25 Oct - 26 Oct
The Studio with a View. Bring your dog, too!
An aerial view of a house surrounded by a forest with autumn foliage.

3. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is AU$776
includes taxes & fees
9 Nov - 10 Nov
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

4. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AU$229
includes taxes & fees
15 Oct - 16 Oct
The Eagles Wing at The CHM - Private Apartment
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

5. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AU$452
includes taxes & fees
27 Oct - 28 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A calm lake with a wooden boat on the shore.

6. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is AU$439
includes taxes & fees
1 Nov - 2 Nov
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A two-story blue house with a porch, surrounded by a garden with orange flowers.

7. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (36 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
The price is AU$222
includes taxes & fees
14 Oct - 15 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

8. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (9 reviews)
"A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing."
United States
Nicole H.
The price is AU$1,111
includes taxes & fees
14 Oct - 15 Oct
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

9. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is AU$501
includes taxes & fees
12 Oct - 13 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

10. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AU$810
includes taxes & fees
14 Oct - 15 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.

11. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is AU$648
includes taxes & fees
19 Oct - 20 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

12. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AU$929
includes taxes & fees
9 Nov - 10 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

13. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is AU$702
includes taxes & fees
8 Nov - 9 Nov
Stunning Glass House nestled in the Vermont wilderness!
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

14. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AU$152
includes taxes & fees
31 Oct - 1 Nov
Cozy Vermont Tiny Home Get Away
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

15. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is AU$1,120
includes taxes & fees
14 Oct - 15 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

16. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is AU$413
includes taxes & fees
3 Nov - 4 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

17. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is AU$274
includes taxes & fees
4 Nov - 5 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A rustic cabin with a covered porch, a small shed, and outdoor seating.

18. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AU$228
includes taxes & fees
25 Oct - 26 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A blue house with a porch, a wooden bench, and a door.

19. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is AU$348
includes taxes & fees
25 Oct - 26 Oct
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A spacious living area with a red sofa, wooden staircase, and a kitchen with a bar.

20. Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA

Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
Dover
10.0 out of 10, Exceptional, (1 review)
"Incredible views, immaculate, spacious, fully sticked kitchen, great pool and amenities. Easy access with great communication from the host. 10/10 recommend"
United States
Danielle F.
The price is AU$493
includes taxes & fees
12 Oct - 13 Oct
Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
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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Top Jacksonville Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"The room was very spacious and clean. Staff was helpful, parking was easy. I would definitely stay here again."
Gloria 3-night trip
Posted 8 hours ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Jacksonville

Everything you need to know about Jacksonville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jacksonville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jacksonville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jacksonville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jacksonville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jacksonville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jacksonville holiday rentals we have selected for you start as low as AU$387 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jacksonville rentals

At Expedia, we put the best Jacksonville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jacksonville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jacksonville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jacksonville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Jacksonville?

Yes, there are holiday rentals close to the most popular sights in Jacksonville, or you can select a more secluded option if you're looking for a relaxing stay. Jacksonville is known for its wineries and parks.

What are some of the best holiday rentals that Jacksonville has to offer?

Bright three-level home with water views, jetted tub, firepit, and pool table: This highly rated holiday home rental in Jacksonville is located in the mountains, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of billiards or a pool table in this rental home to help you unwind.

How many holiday rentals are there in Jacksonville?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Jacksonville stay.

What’s there to see and do in Jacksonville?

Jacksonville Pond and Stickney Hill are a couple of lovely local spots to get outside and enjoy nature. H.O. Cook State Forest and Molly Stark State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Jacksonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jacksonville. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.