Jacksonville Holiday Rentals

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Holiday Rentals in Jacksonville

Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, 23 reviews
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Bright three-level home with water views, jetted tub, firepit, and pool table
8.4 out of 10, Very good, 20 reviews
"This is a beautiful log cabin! Setting is quiet and picturesque and easy to find. The house is well maintained and has everything you need. We cooked in all nights and enjoyed the firepit in the cool spring weather. On arrival house was immaculate, beds made and towels set out. They provide a book of brochures on what to do in the area. Not to miss- the North River bakery right down the street! They have a great selection and even have prepared family meals to go. We will be staying again!"
Bright three-level home with water views, jetted tub, firepit, and pool table
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, 47 reviews
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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Bear Creek Cabin
10.0 out of 10, Exceptional, 14 reviews
"Very well thought out rental home. Everything you could possibly need for cooking and all thought out to reduce your time cleaning and more time on the river. No issues and we had a great time. Thanks again,"
The price is NZ$978
per night
6 Jun - 7 Jun
Bear Creek Cabin
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 34 reviews
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, 117 reviews
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, 16 reviews
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, 28 reviews
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
8.8 out of 10, Excellent, 38 reviews
"The home location, layout were awesome. Pics must be older as there was maintenance needed on the basketball/tennis court, pool, and shuffleboard room. Our bachelor party had a good time, once some updates are done, could be a 5 start spot."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 25 reviews
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, 14 reviews
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, 4 reviews
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, 93 reviews
"Cute house at the base of Mount Greylock. Very clock to hiking chairs and several dining options. Awesome sitting area in the backyard which was fenced in. Perfecy for a quick getaway with our three children and two dogs."
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, 194 reviews
"Great all around, would book again"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, 8 reviews
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
The price is NZ$1,793
per night
11 Jun - 12 Jun
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Wilmington Vacation Rental Near Hiking and Skiing!
10.0 out of 10, Exceptional, 9 reviews
"Beatiful weekend get away."
Wilmington Vacation Rental Near Hiking and Skiing!
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
10.0 out of 10, Exceptional, 25 reviews
"Great home, truly beautiful surroundings and easy drive to lots of stuff. We tackled Mass MoCA, kayaking in Brattleboro and mountain adventures at Bromley. Plus all the small towns and pit stops along the way. Very family friendly house with basement for older kids and well child-proofed for any youngsters."
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
6.0 out of 10, 8 reviews
"We loved staying in the Newfane home! I was a bit worried at 1st from reading the reviews but it was great. The house was nice and cozy. The sauna and steam tub were AMAZING. We really enjoyed the quiet and we were so close to such great restaurants. We would love to come back!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Rustic Retreat: Cozy Log Cabin
9.6 out of 10, Exceptional, 4 reviews
"The cabin is very nice. It is in good shape. It is well decorated. It is very comfy, and it has everything you could possibly need. It is very close to the town of Wilmington, hiking trails, fishing, pond, lakes, and rivers. Sarah, the owner, was very responsive to any questions or needs. There’s a very nice eclectic restaurant in Wilmington that we really enjoyed called Jezebel. There is a high likelihood we would be coming back at some point in the future."
Rustic Retreat: Cozy Log Cabin
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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.

Other types of properties in Jacksonville you may be interested in

Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, 23 reviews
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, 1,001 reviews
"Very comfortable and relaxed "
The price is NZ$157
per night
9 Jun - 10 Jun
Colonial Motel And Spa
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, 1,009 reviews
"Fireplace was very nice. Room was adequate."
The price is NZ$127
per night
12 Jun - 13 Jun
The Covered Bridge Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jacksonville holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jacksonville. 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 Jacksonville. 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 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 holiday 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 Jacksonville short-term rentals, that won’t be hard to do.

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?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This holiday home rental outside of Jacksonville is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Jacksonville?

With 5 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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