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Jacksonville Vacation Rentals

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Our top choices for Jacksonville vacation rentals

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, (7 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 CA $519
CA $834 total
includes taxes & fees
Nov 16 - Nov 17
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

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

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (9 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 CA $163
CA $322 total
includes taxes & fees
Nov 18 - Nov 19
The Studio with a View. Bring your dog, too!

3. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (16 reviews)
"Very peaceful backyard!! Great back deck!!"
United States
Jacqueline M.
The price is CA $284
CA $658 total
includes taxes & fees
Nov 18 - Nov 19
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

4. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (7 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $143
CA $181 total
includes taxes & fees
Nov 18 - Nov 19
The Eagles Wing at The CHM - Private Apartment

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 CA $101
CA $444 total
includes taxes & fees
Nov 18 - Nov 19
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

6. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
The price is CA $125
CA $543 total
includes taxes & fees
Nov 16 - Nov 17
Chalet Mount Snow/Stratton Skiing/hiking

7. 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 CA $143
CA $421 total
includes taxes & fees
Nov 30 - Dec 1
Cozy 3 bedroom condo 2.5 miles to Mount Snow

8. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (3 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is CA $103
CA $135 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Vermont Tiny Home Get Away

9. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
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 CA $168
CA $519 total
includes taxes & fees
Nov 16 - Nov 17
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $246
CA $798 total
includes taxes & fees
Nov 16 - Nov 17
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

11. 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 CA $638
CA $1,022 total
includes taxes & fees
Nov 18 - Nov 19
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

12. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is CA $248
CA $888 total
includes taxes & fees
Nov 22 - Nov 23
Cozy Cedar Cabin 8 Min to Mount Snow

13. 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 CA $131
CA $245 total
includes taxes & fees
Nov 16 - Nov 17
2 Twin beds on 1st floor with En-suite bathroom.

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, (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 CA $280
CA $736 total
includes taxes & fees
Nov 16 - Nov 17
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is CA $458
CA $1,070 total
includes taxes & fees
Nov 17 - Nov 18
Walk To Town, Hottub, Firepit, Games, Mt Snow

16. 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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is CA $128
CA $212 total
includes taxes & fees
Nov 17 - Nov 18
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

17. 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 CA $245
CA $706 total
includes taxes & fees
Nov 30 - Dec 1
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

18. 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 CA $243
CA $409 total
includes taxes & fees
Nov 23 - Nov 24
Wellness Getaway with a Personal Sauna, and Private River Beach!

19. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is CA $415
CA $909 total
includes taxes & fees
Nov 16 - Nov 17
Modern Mount Snow Gnarvana - Steps to Carinthia

20. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $164
CA $282 total
includes taxes & fees
Nov 16 - Nov 17
Private room with En-suite bathroom Marigold Room
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

Find out more about Jacksonville

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Jacksonville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.