Jacksonville vacation rentals

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Top-rated vacation rentals in Jacksonville

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Jacksonville

4.84 out of 5 average rating, 269 reviews

Claudia's Retreat Sanctuary

Retreat here on my 6 acres of madrone forest with pastoral views, 2 meditation labyrinths- yet only 3 miles to the quaint, historic town of Jacksonville, Oregon, home of Britt Festival, 35 minutes to Ashland and 1.5 hours to Mt. Shasta or Crater Lake. This guest suite in the lower level of my house and has uphill access to the hot tub by the garden. Book a Sacred Sound bath session with Tibetan and crystal bowls & Paiste gongs for $70 during your stay. Massage chair available too. Simply divine!

Dec 5 – 12

$69 per night

Guest favorite

Guest suite in Jacksonville

4.97 out of 5 average rating, 357 reviews

Spring Savings-Private 2-Bedroom Suite in J-ville

Welcome to the Nathe Nest where you’ll enjoy a little piece of heaven in the quaint historic town of Jacksonville. The "Suite" is cozy, convenient, and your "Welcome Baskets" are filled with plush towels and each closet has two robes to make you feel right at home. Owner lives in the main part of the house with an adjoining door to the Sunroom only, it has locks and blinds for privacy. Very rarely do you hear anything from the owners side. EXTRA GUEST FEE over 2 GUESTS $30 PER PERSON/PER NIGHT.

Sep 12 – 19

$116 per night

Guest favorite

Guest suite in Jacksonville

4.91 out of 5 average rating, 189 reviews

2-bedroom suite, only 1 mile to Jacksonville

Family and Senior friendly In Jacksonville, 1 mile to town. Cozy, quiet, scenic, isolated in the hills. Modern home with central A/C and heat, good cell signal, ceiling fans . Master Bedroom, key pad entry, King bed, fine sheets, TV with Amazon Prime, Bathroom, large towels, large jetted tub, double sink. Kitchenette with fridge-freezer, microwave, George Foreman grille, double burner, coffee pot, toaster, and blender. Adjacent bedroom Queen bed and desk with power strip. Private entry door.

Sep 26 – Oct 3

$116 per night

Guest favorite

Home in Jacksonville

4.99 out of 5 average rating, 249 reviews

Britt Bungalow in the Heart of Jacksonville

An elegant single level newly built (2019) private 2 bed/2 bath cottage with 17' ceilings, #1 Dreamcloud mattress in Master, substantial natural light & family friendly fenced in front & PRIVATE backyard. EV Charger. Less than 2-blocks from dining & the lovely Britt Festival Concert venue. Enjoy historic tours on trolly out the front door. FAMILY: Park & walkable to grocery store. FITNESS: Local gym near by and hiking trails. RELAX: Free standing bath tub, bench swing on porch, & fireplace

Nov 16 – 23

$242 per night

Superhost

Cottage in Jacksonville

4.9 out of 5 average rating, 175 reviews

Farm Cottage on River - Applegate Wine Trail

Recently repainted and deep cleaned, cottage on a 5-acre, Applegate River farm near vineyards. This is a cozy cottage on "Red Barn Farm.” Enjoy a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit with complimentary s’mores kit or walk down to the river and breath. We are 15 minutes from the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival. Wine Country Farm Stay dot come.

Aug 25 – Sep 1

$122 per night

Guest favorite

Cottage in Central Point

4.98 out of 5 average rating, 390 reviews

Country Garden Cottage

Newly remodeled Garden Cottage with living area/kitchenette, bedroom, and bathroom. Cottage has high ceilings, ceramic tile floors, quartz countertop, cherry wood cabinets and new mini-split heater/air conditioner. It is bordered on two sides by a garden common area with seating, fountain, and a grape vine covered pergola. New Roku TV installed. Conveniently located: * 5 min to I-5 * 10 min to airport * 3 min to Central Point * 10 min to Medford * 5 min to Jacksonville * 25 min to Ashland

Oct 4 – 11

$85 per night

Guest favorite

Treehouse in Jacksonville

4.98 out of 5 average rating, 186 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

Sep 14 – 21

$185 per night

Guest favorite

Guest suite in Jacksonville

4.84 out of 5 average rating, 217 reviews

My Little Tuscany: vineyard view, deck & hot tub

This is a scenic stop between PDX and SF and its own destination. One guest says " Her home has a magic of its own." Simple, elegant, and a great base for wine-tasters, paraglider, or roadtrippers. If a house surrounded by nature, vineyards, paraglider pilots, creativity and occasional other travelers sounds interesting, you'll love it here. As a local tourism coordinator, I can direct you to the top attractions. Note: this is a self-contained unit but attached to the main house!

Sep 3 – 10

$88 per night

Guest favorite

Guest suite in Medford

4.96 out of 5 average rating, 125 reviews

Vineyard Views from 2 Bdrm Suite on the Farm

The guesthouse on our little farm overlooks the vineyard and the fields beyond. We are in the perfect spot to easily access many of the wonderful things Southern Oregon has to offer. Explore wineries, including our own, hiking trails, the Britt festival, and more! This is a new space with lots of amenities, including an outdoor grill, kitchenette with fridge and hot plate, and full-size sleeper-sofa. Pack & play and other baby/child amenities are available upon request.

May 20 – 27

$128 per night

Guest favorite

Guesthouse in Jacksonville

4.97 out of 5 average rating, 133 reviews

Valhalla Cabin, King Bed, Hiking, close to Britt

Tranquility & hiking. 128 AC of wooded acreage to hike on. The flowers bloom in the spring! Come and see! We are located about 20 min from The Britt in Jacksonville. Check out their venue and list of performers! ***This is a NO SMOKING IN OR OUT of the unit/property, This cabin is NOT suitable for children, No animals allowed EXCEPT for service dogs. When there is snow, 4-wheel vehicles are advised***

Jul 11 – 18

$103 per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 154 reviews

Starthistle Cottage in Applegate wine country

Rural cottage in the beautiful Applegate Valley. Peaceful with beautiful views of the landscape and wildlife. Closest lodging to Woodrat Mountain launch for paragliders & hang gliders. Nestled in the heart of the Applegate Wine Trail and the Southern Oregon Lavender Trail. Close to historical Jacksonville for the Britt Festival. Easy access to Applegate Lake and surrounding hiking trails.

Jul 12 – 19

$123 per night

Guest favorite

Guesthouse in Medford

4.95 out of 5 average rating, 152 reviews

Cottage with jetted tub and fine linens

Nestled in rich farmland just north of historic Jacksonville and Britt Gardens, this cottage is just minutes away from everything the Rogue Valley has to offer. Whether you are visiting to taste award-winning wines, craft-brewed beers, experience outdoor concerts at the Britt - or all of the above - you will find you are right in the middle of the action.

Oct 16 – 23

$92 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Jacksonville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Jacksonville's top sights

Britt Festival Pavilion103 locals recommend

Bella Union Restaurant60 locals recommend

The Schoolhaus Brewhaus23 locals recommend

Back Porch Bar & Grill21 locals recommend

Jacksonville Inn Dinner House17 locals recommend

GoodBean Jacksonville42 locals recommend

Other great vacation rentals in Jacksonville

Guest favorite

Guesthouse in Medford

4.97 out of 5 average rating, 231 reviews

Mel-Ohana: your favorite country retreat!

Aug 13 – 20

$86 per night

Guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 581 reviews

Orchard Home Cottage * ~ Private, Cozy, Peaceful *

Jun 21 – 28

$75 per night

Guest favorite

Home in Jacksonville

5.0 out of 5 average rating, 207 reviews

Unwind at a Luxury Cottage in Jacksonville's Historic Core

Sep 7 – 14

$175 per night

Guest favorite

Guesthouse in Gold Hill

4.92 out of 5 average rating, 165 reviews

Octagon Studio / Beautiful Rogue River property

Jan 2 – 9

$125 per night

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 703 reviews

BEE WELL Organic Spa Garden Studio

Jul 21 – 28

$97 per night

Guest favorite

Guest suite in Medford

4.89 out of 5 average rating, 160 reviews

The Wolf Den: newly renovated studio space!

Jan 15 – 22

$105 per night

Guest favorite

Yurt in Grants Pass

4.97 out of 5 average rating, 653 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

Dec 1 – 8

$88 per night

Guest favorite

Apartment in Medford

4.99 out of 5 average rating, 237 reviews

Suite Madrona

Oct 11 – 18

$80 per night

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Other great vacation rentals in Jacksonville

Guest favorite

Guesthouse in Medford

4.96 out of 5 average rating, 289 reviews

Cabo Cottage, private guest house.

Aug 18 – 25

$87 per night

Guest favorite

Tiny home in Grants Pass

4.97 out of 5 average rating, 200 reviews

Tiny Cabin in the Woods w/ Hot Tub and Firepit

Feb 2 – 9

$116 per night

Guest favorite

Cottage in Grants Pass

4.96 out of 5 average rating, 193 reviews

Applegate Wine Country cottage!

Sep 6 – 13

$126 per night

Guest favorite

Guesthouse in Medford

4.95 out of 5 average rating, 524 reviews

Erin’s Guesthouse w/parking, patio & self check-in

Jul 27 – Aug 3

$86 per night

Guest favorite

Farm stay in Jacksonville

5.0 out of 5 average rating, 30 reviews

Cozy Family Ranch Cottage! Near Vineyards & Lake!

Feb 2 – 9

$98 per night

Guest favorite

Cabin in Jacksonville

5.0 out of 5 average rating, 62 reviews

Private & Cozy Treetop Cabin in Historic J-vile

Aug 27 – Sep 3

$102 per night

Guest favorite

Home in Jacksonville

5.0 out of 5 average rating, 10 reviews

Historic 1875 Kitchen House

Oct 4 – 11

$90 per night

Guest favorite

Cottage in Central Point

4.91 out of 5 average rating, 57 reviews

Idyllic 2bd 1ba Cottage close to town & wineries

Nov 15 – 22

$100 per night

Show all

Quick stats about vacation rentals in Jacksonville

Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
2.5K reviews
Nightly prices starting at
$40 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Jacksonville?
Yes! Work meets play with ease at over 30 vacation rentals in Jacksonville featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Jacksonville?
Four-legged friends are welcome in Jacksonville. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in hotel rentals in Jacksonville?
Experience the best of Jacksonville with our hotel rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Jacksonville?
Jacksonville has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Jacksonville have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Jacksonville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jacksonville have wifi?
Absolutely! We offer over 20 house rentals with wifi in Jacksonville. Enjoy a tailored experience with all the comforts you desire.

Jacksonville vacation rentals

Top-rated vacation rentals in Jacksonville

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Jacksonville vacation rentals

Stay near Jacksonville's top sights

Other great vacation rentals in Jacksonville

Guesthouse in Medford

Guesthouse in Medford

Home in Jacksonville

Guesthouse in Gold Hill

Guesthouse in Central Point

Guest suite in Medford

Yurt in Grants Pass

Apartment in Medford

Other great vacation rentals in Jacksonville

Guesthouse in Medford

Tiny home in Grants Pass

Cottage in Grants Pass

Guesthouse in Medford

Farm stay in Jacksonville

Cabin in Jacksonville

Home in Jacksonville

Cottage in Central Point

Quick stats about vacation rentals in Jacksonville

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Jacksonville?

Are there pet-friendly vacation rentals in Jacksonville?

How much does it cost to stay in hotel rentals in Jacksonville?

Are there family-friendly vacation rentals in Jacksonville?

Do house rentals in Jacksonville have self check-in?

Do house rentals in Jacksonville have wifi?

Destinations to explore