Jacksonville Vacation Rentals from $157: Search Short-Term 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

Whitingham

Ben B.

$535 nightly

Aug 15 - Aug 16

Total with taxes and fees

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

Whitingham

Jacklyn D.

$469 nightly

Aug 31 - Sep 1

Total with taxes and fees

Coffee/tea maker, fridge, microwave, stovetop

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

Whitingham

Nicole H.

$705 nightly

Aug 19 - Aug 20

Total with taxes and fees

Smart TV, fireplace, video games, DVD player

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

Wilmington

Nicholas G.

$732 nightly

Aug 17 - Aug 18

Total with taxes and fees

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

Brattleboro

s p.

$221 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

West Dover

Dan G.

$623 nightly

Aug 15 - Aug 16

Total with taxes and fees

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

Wilmington

Jack & Heather G.

$592 nightly

Sep 9 - Sep 10

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

8. Spacious 5BR w/ Hot Tub & Games

Colrain

Maureen A.

$623 nightly

Aug 16 - Aug 17

Total with taxes and fees

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Top Jacksonville Hotel Reviews

Hampton Inn Brattleboro

10/10 Excellent

"Too tired to think about it. Sorry."

Knotty Pine

8/10 Good

"Staff was very nice and helpful. Rooms were nice but dated. Really not a bad place to stay. The only complaints were that the washing machines were broken so we couldn't do laundry (we're hiking the AT/Long Trail and very dirty clothes) and the breakfast was disappointing (looking forward to a hot breakfast but they only offer a granola bar, fruit cup and juice in a brown bag) but it was ok for us. Another plus is a Wal-mart, Price Chopper, Starbucks, and restaurants very close for resupply and chow time."

Windmill Motel Restaurant

10/10 Excellent

"I love the outdoor seating area with the tent and outdoor couches and I love the colors and textures used for the room I stayed in. When I checked in, I was hot from being at SoulFest and the owners gave me a cloth hand fan for free! When I came home that night, I was hungry and there were chips and chocolates in my room! That was wonderful and thoughtful. They also sell food in the office, if you need something more substantial. The mattress and pillows were so comfortable that I had trouble getting myself up the next morning! Slept like a rock. 10/10 for the Windmill! Can't wait to see what the restaurant will be like when it opens! I will definitely come back next year, if there is availability!"

Latchis Hotel

8/10 Good

"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."

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 $157 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?

While exploring the area, visit family-friendly sights like Brattleboro Bowl, or get outside and enjoy nature at Jacksonville Pond. 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.

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Check prices for these dates

Our top choices for Jacksonville vacation rentals

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

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

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

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

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

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

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

8. Spacious 5BR w/ Hot Tub & Games

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

10. 5BR Berkshire Home Mins To The Mountain

11. 3 Mi to Mount Snow: Spacious West Dover Home

12. Bear Creek Cabin

13. The Greylock Cabin

14. Lovely 2nd Floor Apartment

15. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

16. Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

17. Riverbend Berkshire East Basecamp - 3 bedrooms available

18. 3 Mi to Mount Snow: Spacious West Dover Home

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

20. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Find vacation rentals that suit your style

Top Jacksonville Hotel Reviews

Hampton Inn Brattleboro

Hideaway Inn Mt. Snow

New Englander Inn Bennington

Hotel Downstreet, an Ascend Collection Hotel

The Porches Inn at Mass MoCA

Vikings Villages Resort

Knotty Pine

Windmill Motel Restaurant

Latchis Hotel

Find out more about Jacksonville

Frequently asked questions

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