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Jacksonville Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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
8.4 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.
The price is HK$2,855
HK$4,779 total
includes taxes & fees
3 Oct - 4 Oct
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.
The price is HK$3,509
HK$5,819 total
includes taxes & fees
30 Sept - 1 Oct
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
The price is HK$1,686
HK$3,892 total
includes taxes & fees
29 Sept - 30 Sept
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.
The price is HK$2,390
HK$5,661 total
includes taxes & fees
28 Sept - 29 Sept
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
The price is HK$1,145
HK$3,160 total
includes taxes & fees
5 Oct - 6 Oct
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.
The price is HK$974
HK$1,970 total
includes taxes & fees
30 Sept - 1 Oct
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.
The price is HK$3,130
HK$5,699 total
includes taxes & fees
9 Oct - 10 Oct
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.
The price is HK$831
HK$3,111 total
includes taxes & fees
5 Oct - 6 Oct
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.
The price is HK$3,636
HK$8,735 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$2,157
HK$4,907 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$1,530
HK$3,989 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$2,252
HK$4,785 total
includes taxes & fees
29 Sept - 30 Sept
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.
The price is HK$396
HK$2,265 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$1,537
HK$4,222 total
includes taxes & fees
6 Oct - 7 Oct
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.
The price is HK$3,138
HK$4,434 total
includes taxes & fees
1 Oct - 2 Oct
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.
The price is HK$689
HK$2,966 total
includes taxes & fees
28 Sept - 29 Sept
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.
The price is HK$2,676
HK$5,035 total
includes taxes & fees
28 Sept - 29 Sept
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
The price is HK$2,981
HK$6,129 total
includes taxes & fees
28 Sept - 29 Sept
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
The price is HK$1,759
HK$4,991 total
includes taxes & fees
30 Sept - 1 Oct
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.
The price is HK$2,079
HK$5,057 total
includes taxes & fees
25 Oct - 26 Oct
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

The White House Inn

The White House Inn

8/10 Good
"Old property with a lot of history."
William P 2-night trip
Posted 2 days ago
The White House Inn

Find out more about Jacksonville

Search for holiday rentals in Jacksonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Jacksonville using one of the methods below:

  • View our selection of featured holiday rentals in Jacksonville
  • Use the map to find apartments and other holiday homes in the Jacksonville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jacksonville while they last

Look no further and take a look at our great range of rental properties in Jacksonville!

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.