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Jacksonville Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
8.4 out of 10, Very good, (5 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.
$541 nightly
The price is $606
Oct 3 - Oct 4
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

2. 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.
$662 nightly
The price is $742
Sep 30 - Oct 1
Total with taxes and fees
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
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
$454 nightly
The price is $508
Sep 29 - Sep 30
Total with taxes and fees
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (63 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
$636 nightly
The price is $718
Sep 29 - Sep 30
Total with taxes and fees
Walk To Town, Hottub, Firepit, Games, Mt Snow
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

5. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$366 nightly
The price is $403
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden interior with a kitchen, bar area, and dining space.

6. 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, (5 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.
$224 nightly
The price is $251
Sep 30 - Oct 1
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

7. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
$667 nightly
The price is $754
Oct 9 - Oct 10
Total with taxes and fees
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

8. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Once we got to know the fireplace, it was a wonderful addition to a very cozy cabin. The house felt loved and each different room had different touches of character and magic. We absolutely loved our stay. "
United States
Sarah K.
$354 nightly
The price is $400
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

9. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
$981 nightly
The price is $1,108
Sep 29 - Sep 30
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

10. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
$560 nightly
The price is $626
Sep 29 - Sep 30
Total with taxes and fees
5BR Berkshire Home Mins To The Mountain
A spacious kitchen with wooden cabinets, a central island with stools, and a fireplace.

11. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
$452 nightly
The price is $511
Sep 29 - Sep 30
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

12. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
$547 nightly
The price is $611
Sep 29 - Sep 30
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

13. 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.
$254 nightly
The price is $287
Sep 30 - Oct 1
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

14. 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, (20 reviews)
"Great place!"
United States
Jack & Heather G.
$508 nightly
The price is $538
Oct 6 - Oct 7
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A log cabin with a balcony, surrounded by trees.

15. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
$506 nightly
The price is $565
Oct 5 - Oct 6
Total with taxes and fees
Bear Creek Cabin
A wooden house with a porch lit by string lights, surrounded by snow.

16. 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.
$338 nightly
The price is $382
Sep 29 - Sep 30
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A pathway through a forest with autumn leaves and a wooden bridge.

17. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
10.0 out of 10, Exceptional, (46 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
$570 nightly
The price is $644
Sep 29 - Sep 30
Total with taxes and fees
Experience Vermont’s Fall Magic at here at the Lemondrop
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

18. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
$710 nightly
The price is $781
Sep 29 - Sep 30
Total with taxes and fees
Spacious Vermont Farmhouse 3 Mi to Mount Snow
A dining area with a long table and chairs, large windows with a view of trees, and a barbecue grill outside.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$627 nightly
The price is $653
Oct 6 - Oct 7
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A wooden deck leading to a dark-colored house with a white door and windows.

20. A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
$572 nightly
The price is $625
Sep 30 - Oct 1
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The hotel was clean and it was quiet in my room. Staff were nice. It was conveniently located"
Lauren 2-night trip
Posted 5 hours ago
Hampton Inn Brattleboro

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 $292 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.