Jacksonville Holiday Rentals

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Holiday Rentals in Jacksonville

Jacksonville Cabin w/ Wraparound Deck & Views
Fridge, microwave, stovetop, dishwasher
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
Fridge, microwave, oven, stovetop
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
Interior
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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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
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
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 24 reviews
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Bear Creek Cabin
Exterior
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 HK$3,127
HK$4,724 total
includes taxes & fees
3 Jun - 4 Jun
Bear Creek Cabin
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Golf
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, 92 reviews
"Wonderful property for family and dog!"
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 33 reviews
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi
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
Dog-friendly chalet cabin with valley view, deck, and private hot tub
TV
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 Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
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!
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, 37 reviews
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Property grounds
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
Interior
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, 7 reviews
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
The price is HK$4,690
HK$8,658 total
includes taxes & fees
4 Jun - 5 Jun
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books
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
Exterior
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!
Property grounds
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
Fridge, microwave, oven, stovetop
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
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
Interior
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
8.4 out of 10, Very good, 12 reviews
"Property was great. We were there to ski at Mt Snow and the location did not disappoint. We were not ski-on ski-off but were so close it didn’t matter. Overall the house was clean and the owner was super responsive. Have it saved to stay again next season."
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Fridge, microwave, oven, stovetop
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very good, 19 reviews
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
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See all available properties in Jacksonville
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
Fridge, microwave, stovetop, dishwasher
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
Exterior
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, 1,004 reviews
"I got the 1 bedroom suite there. It was very spacious and comfortable. The perfect place if you want to sleep well. The bedding was ultra comfortable and I had everything I needed."
The price is HK$766
HK$843 total
includes taxes & fees
2 Jun - 3 Jun
Colonial Motel And Spa
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, 925 reviews
"We had a warm welcome when we got to the hotel. Any questions we had, they had the right information. Everything thing was clean and up to date. I love the fact that though out the lobby and the rooms they had local artists and students artwork. "
The price is HK$1,119
HK$1,250 total
includes taxes & fees
16 Jun - 17 Jun
Hotel Downstreet
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.

Search for holiday rentals in Jacksonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Jacksonville using one of the methods below:

  • View our selection of featured holiday rentals in Jacksonville
  • Use the map to find apartments and other holiday homes in the Jacksonville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jacksonville while they last

Look no further and take a look at our great range of rental properties in Jacksonville!

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.

Recent reviews of Jacksonville properties
Expedia verified reviews

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

5/5 Excellent
Nice stay! Good value!
"We were pleasantly surprised at this Comfort Inn. Our room was very clean and spacious. Mattress, sheets and pillows were very comfortable. Hot water flowed almost instantly. The accessible unit had a great walk in shower and a shower bench! Breakfast buffet was fresh and plentiful. Will definitely recommend this for a reliable place to stay in Brattleboro."
A verified traveller stayed at Comfort Inn & Suites Brattleboro I-91
Posted 1 day ago
Comfort Inn & Suites Brattleboro I-91