Jacksonville Vacation Rentals

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Jacksonville vacation rentals

Living area

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
8.8 out of 10, Excellent, (3 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.
$533 nightly
The price is $597
May 31 - Jun 1
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
9.8 out of 10, Exceptional, (14 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
$145 nightly
The price is $157
May 31 - Jun 1
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
10.0 out of 10, Exceptional, (2 reviews)
"Cozy and clean yurt in the woods surrounded by sounds of hooting owls and a super friendly and help host made for the perfect family weekend. Can’t wait to plan another stay. Made roughing it not rough at all. "
United States
Allisha C.
$133 nightly
The price is $144
Jun 1 - Jun 2
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"Beautifully appointed and comfortable. "
United States
Emily Kate G.
$175 nightly
The price is $195
May 31 - Jun 1
Total with taxes and fees
Lovely 2nd Floor Apartment
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (17 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
$383 nightly
The price is $426
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-Site: Cozy Falls Brook Cabin
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
$167 nightly
The price is $187
May 31 - Jun 1
Total with taxes and fees
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
$211 nightly
The price is $236
Jun 7 - Jun 8
Total with taxes and fees
Brookside cottage near the mountains and outdoor recreation
Outdoor pool, a heated pool

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.
$280 nightly
The price is $317
May 31 - Jun 1
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior detail

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
$251 nightly
The price is $280
May 31 - Jun 1
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (32 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
$128 nightly
The price is $143
May 31 - Jun 1
Total with taxes and fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
$182 nightly
The price is $206
May 31 - Jun 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
$376 nightly
The price is $410
Jun 15 - Jun 16
Total with taxes and fees
Hiking Trails On-site: Cozy Falls Brook Cabin
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$336 nightly
The price is $380
May 31 - Jun 1
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
$173 nightly
The price is $193
Jun 1 - Jun 2
Total with taxes and fees
Rose room Victorian home queen bed private bath
Private kitchen

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, (2 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.
$247 nightly
The price is $277
Jun 3 - Jun 4
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
$189 nightly
The price is $211
Jun 1 - Jun 2
Total with taxes and fees
Private bed with En-suite bathroom Marigold Room
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
$378 nightly
The price is $423
Jun 3 - Jun 4
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Outdoor dining

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
$278 nightly
The price is $312
Jun 2 - Jun 3
Total with taxes and fees
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Smart TV, fireplace, Netflix, streaming services

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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$382 nightly
The price is $432
Jun 1 - Jun 2
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.6 out of 10, Exceptional, (5 reviews)
"Nice place"
United States
Tom
$245 nightly
The price is $274
Jun 22 - Jun 23
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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

Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"This place is amazing! Very clean, well maintained, super accommodating, and they take continental Breakfast to a whole new level. it looks like a portrait cuz of the care and effort put into it. Great way to start your day Coffee, juice, milk, fruit, and I mean fruit, every fruit you can think of, nuts, variety of assorted bagels, bread, muffins, yogurt. But most of all the, energy, happy, positive, and helpful."
Stephanie 1-night trip
Posted 5 hours ago
Willows Motel Williamstown

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 $143 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.

Explore a world of travel with Expedia

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?

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included: This vacation home rental near 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 a hot tub.

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.