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Jacksonville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Jacksonville vacation 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.
$576 nightly
The price is $645
Oct 19 - Oct 20
Total with taxes and fees
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, (7 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.
$232 nightly
The price is $260
Nov 2 - Nov 3
Total with taxes and fees
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
$457 nightly
The price is $512
Nov 2 - Nov 3
Total with taxes and fees
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A window with a view of a forested landscape and a wooden deck.

4. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
$435 nightly
The price is $487
Nov 2 - Nov 3
Total with taxes and fees
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
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.
$273 nightly
The price is $309
Oct 19 - Oct 20
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

6. 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.
$168 nightly
The price is $190
Oct 23 - Oct 24
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
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
$132 nightly
The price is $148
Oct 18 - Oct 19
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
A calm lake with a wooden boat on the shore.

8. 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.
$271 nightly
The price is $306
Nov 1 - Nov 2
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

9. 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.
$705 nightly
The price is $790
Oct 22 - Oct 23
Total with taxes and fees
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$621 nightly
The price is $648
Oct 20 - Oct 21
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A wooden house with a porch lit by string lights, surrounded by snow.

11. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$407 nightly
The price is $460
Nov 4 - Nov 5
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

12. 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.
$319 nightly
The price is $361
Oct 18 - Oct 19
Total with taxes and fees
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.

13. 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
$538 nightly
The price is $572
Oct 19 - Oct 20
Total with taxes and fees
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.

14. 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.
$404 nightly
The price is $457
Oct 21 - Oct 22
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

15. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
$92 nightly
The price is $104
Nov 11 - Nov 12
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

16. 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.
$454 nightly
The price is $509
Nov 8 - Nov 9
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

17. 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.
$683 nightly
The price is $772
Oct 19 - Oct 20
Total with taxes and fees
Walk To Town, Hottub, Firepit, Games, Mt Snow
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

18. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
$165 nightly
The price is $184
Nov 4 - Nov 5
Total with taxes and fees
2 Twin beds on 1st floor with En-suite bathroom.
A cozy cabin interior with two sofas, a fireplace, and a television mounted above it.

19. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
$567 nightly
The price is $641
Oct 26 - Oct 27
Total with taxes and fees
Cozy Cedar Cabin 8 Min to Mount Snow
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

20. 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.
$254 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
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

Colonial Motel

Colonial Motel

10/10 Excellent
"Value for money. Clean and conveniently located. Friendly staff."
Swaraj 2-night trip
Posted 17 hours ago
Colonial Motel

Find out more about Jacksonville

Everything you need to know about Jacksonville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jacksonville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jacksonville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Jacksonville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $260 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jacksonville rentals

At Expedia, we put the best Jacksonville vacation 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 vacation.

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 vacation rental in Jacksonville?

Yes, we give you a choice of vacation rentals near the most popular attractions in Jacksonville, or you can select a more secluded option if you want a relaxing place to stay. Jacksonville is known for its wineries and parks.

What's the top vacation rental that Jacksonville has to offer?

Bright three-level home with water views, jetted tub, firepit, and pool table: This highly rated vacation 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 the pool table in this rental home to help you unwind.

How many vacation rentals are there in Jacksonville?

With 4 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Jacksonville like?

A vacation rental is a private property you can stay in for a long or short time in Jacksonville. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.