Holiday rentals in Jacksonville

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Top-rated holiday rentals in Jacksonville

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

Guest favourite

Guest suite in Jacksonville

4.84 out of 5 average rating, 267 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!

22–29 May

$107 SGD per night
Guest favourite

Guest suite in Jacksonville

4.97 out of 5 average rating, 355 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.

28 May – 4 Jun

$180 SGD per night
Guest favourite

Home in Jacksonville

4.99 out of 5 average rating, 248 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

22–29 Jan

$377 SGD per night

Popular amenities for Jacksonville holiday rentals

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 holiday rentals in Jacksonville

Guest favourite

Guest suite in Jacksonville

4.91 out of 5 average rating, 189 reviews

2-bedroom suite, only 1 mile to Jacksonville

21–28 May

$200 SGD per night
Guest favourite

Guest house in Central Point

4.94 out of 5 average rating, 698 reviews

BEE WELL Organic Spa Garden Studio

7–14 Aug

$114 SGD per night
Guest favourite

Guest house in Medford

4.96 out of 5 average rating, 228 reviews

Mel-Ohana: your favorite country retreat!

12–19 Jun

$149 SGD per night
Guest favourite

Guest house in Gold Hill

4.91 out of 5 average rating, 164 reviews

Octagon Studio / Beautiful Rogue River property

22–29 Oct

$195 SGD per night
Guest favourite

Tiny home in Shady Cove

4.95 out of 5 average rating, 194 reviews

Modern Tiny House w/ Hot Tub

29 Aug – 5 Sep

$187 SGD per night
Guest favourite

Home in Jacksonville

5.0 out of 5 average rating, 207 reviews

Unwind at a Luxury Cottage in Jacksonville's Historic Core

9–16 Nov

$273 SGD per night
Guest favourite

Guest house in Central Point

4.92 out of 5 average rating, 128 reviews

Southern Comfort - Hot tub - Modern - Relaxing

7–14 Sep

$218 SGD per night
Guest favourite

Flat in Medford

4.99 out of 5 average rating, 235 reviews

Suite Madrona

3–10 Dec

$127 SGD per night
Guest favourite

Guest house in Medford

4.92 out of 5 average rating, 343 reviews

The Greenwood Villa

8–15 Apr

$204 SGD per night
Guest favourite

Farm stay in Jacksonville

5.0 out of 5 average rating, 25 reviews

Cozy Family Ranch Cottage! Near Vineyards & Lake!

13–20 Sep

$152 SGD per night
Guest favourite

Cabin in Jacksonville

5.0 out of 5 average rating, 60 reviews

Private & Cozy Treetop Cabin in Historic J-vile

7–14 Jul

$159 SGD per night
Guest favourite

Cottage in Jacksonville

4.97 out of 5 average rating, 32 reviews

Tigers Den/#1 Best Location/Romantic & Luxurious

6–13 Jan

$227 SGD per night

Quick stats about holiday 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

2.8K reviews

Nightly prices starting at

$54 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Jacksonville