Jacksonville Holiday Rentals from €590: Search Short-Term Rentals

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Holiday Rentals in Jacksonville

"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "

"We stayed three nights here. Just the two of us. I felt the pictures were misleading. Much smaller than expected. Since it was just the two of us it was perfect. "

"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...

"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...

"This was possibly one of the best VRBO experiences for me. Flawless in all respects"

"The home was beautiful and we enjoyed our stay! The only thing about the location, it’s very remote. We had an event in North Adams and had a nearly impossible time getting a ride share service or taxi to come pick us up. Other than that, a wonderful stay!"

includes taxes & fees

2 Dec - 3 Dec

"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."

"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"

"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"

"Amazing place. Offered everything we needed and more. Very warm and comfortable. Well appointed too. We will be back for a longer stay in 2025. "

9 bedrooms, desk, iron/ironing board, free WiFi

"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...

"We enjoyed our stay at the tiny home!"

"The cabin was the perfect weekend getaway. We had issues with connecting the projector to the internet and finally gave up on trying to connect but other then that the overall experience was great. Will be staying here again in the future. "

"We had a nice stay at this lovely place. It's tucked away at the end of a dirt road. We never saw another human only some wild turkeys. It was great to sit in the hot tub and look at the seasonal stream and the beautiful trees surrounding the property. "

"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "

"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"

"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"

"Beautiful cabin! Right in the middle of nature with plenty of things to do nearby. Host was exceptional!"

1 bedroom, iron/ironing board, WiFi, bed sheets

"My stay with a friend at this location was extremely pleasant overall; the home was well furnished, stocked, and the surroundings of rural Vermont were beyond gorgeous. The interior was very well cleaned when I arrived, though my friend and I very quickly noticed that there was a distinct septic-like odor in the house's central hallway area and the home's exterior (walking up to the entryway, etc). This smell persisted throughout the duration of the stay, but was most noticeable on days where...

"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "

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Other types of properties in Jacksonville you may be interested in

"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "

Hypo-allergenic bedding, laptop workspace, blackout curtains

"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "

includes taxes & fees

2 Dec - 3 Dec

"The staff are nice "

includes taxes & fees

1 Dec - 2 Dec

Find out more about Jacksonville

Everything you need to know about Jacksonville holiday rentals

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

Jacksonville holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jacksonville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jacksonville holiday rentals we have selected for you start as low as €590 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jacksonville rentals

At Expedia, we put the best Jacksonville holiday 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 holiday.

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.

Recent reviews of Jacksonville properties

5/5 Excellent

Look no further, way better than the Hampton Inn

"This is the best value stay in Bennington. As a parent of a Bennington College student, we have stayed at several properties in the area, including this one before it was renovated. The rooms are bright and clean. The bed and linens were comfortable. The furniture is new. The TV is smart and you can get Netflix or other streaming services. The bathroom was a shower only, but it was brand new and the water pressure was great. The temperature in the room was comfortable, I think the heating cooling system is new. Coffee bar in the lobby a little lacking, kuerig, with hazelnut coffee mate, a plain choice would be great. Staff was amazingly kind and adequate. They are not on the property 100% of the time, but that is okay. "

A verified traveller stayed at The Hotel Vervana at Bennington

Posted 2 days ago

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

5/5 Excellent

"Sat outside for a few minutes at a table and chairs at the fire was awesome. The person at check in was extremely welcoming, cookies in the lobby. People relaxing. Inside looks pretty and clean. Beds are pretty comfy, room is spacious. They accommodated my requests. The little store downstairs is perfect, have snacks, frozen meals, earrings and.. post cards!!!! Only a couple things is that the showers maybe need to be recocked? They look they arent as nice as everything else.Will definitely stay here again. Excited for breakfast. "

A verified traveller stayed at Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

Posted 3 days ago

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?

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included: This holiday home rental outside of Jacksonville is located on a lake, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals are there in Jacksonville?

With 6 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?

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

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Holiday Rentals in Jacksonville

Check Jacksonville holiday rental availability

Holiday Rentals in Jacksonville

Jacksonville Cabin w/ Wraparound Deck & Views

Bright three-level home with water views, jetted tub, firepit, and pool table

Walk to Mount Snow, Cozy, Clean and Comfortable!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Seasons On Mount Snow - Ski-in/Ski-out

Bear Creek Cabin

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi

Mount Snow's Best View - Sleeps 8-10

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Perfect for Leaf Peeping w/Bar Room, Hot Tub

Wilmington Vacation Rental Near Hiking and Skiing!

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Other types of properties in Jacksonville you may be interested in

Jacksonville Cabin w/ Wraparound Deck & Views

Hotel Downstreet

Colonial Motel And Spa

Find out more about Jacksonville

Recent reviews of Jacksonville properties

The Hotel Vervana at Bennington

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

Comfort Inn & Suites Brattleboro I-91

The Covered Bridge Inn

Chalet 239

Mount Snow Grand Summit Resort

Hampton Inn Brattleboro

The Putney Inn

Latchis Hotel

Frequently asked questions