Vacation rentals in Jacksonville

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.

Britt Bungalow in the Heart of Jacksonville

The Britt Bungalow is an Award Winning boutique style stay, created and designed by the owner and host. This is a private 2 bed/2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, fireplaced open living room with an abundance of natural light throughout. You will want for nothing during your stay. It is in the historical heart of Jacksonville Oregon just 2 blocks from the trolly, all the best restaurants, boutiques, Britt Gardens, and much more

B.F. Dowell House

Originally constructed in 1861, the historic B.F. Dowell house has been beautifully revived. Situated within walking distance of downtown, the home provides guests with easy access to the towns charming cultural fixtures as well as a variety of quaint stores. The market across the street may help guests utilize the homes large, well-equipped kitchen. Full baths adjoin each bedroom, an additional bathroom adjoins a laundry room. The homes porch opens to a patio that accompanies a spacious lawn.

Private & Cozy Treetop Cabin in Historic J-vile

Welcome to your private cabin up in the trees, just 3 miles from sought after Historic Jacksonville, Oregon-where award winning restaurants, wineries, and adventures await! Stay for a few days or a couple months and we will take care of you just the same! Set among mature Madrones and Pines with views of the evergreen mountains, you will be using all your senses to discover what Oregon is all about. Lots of fun wildlife! A well behaved pet is welcome with approval. DM for dates not listed.

The Birdhouse Retreat| Views & Hot Tub

Take it easy at this unique and tranquil getaway. Immerse yourself with the sound of the forest gazing at the Applegate valley and lavender farms below. Walk around in over 10 acres of forest and enjoy a forest bath and sounds of the river below. Minutes from renowned Applegate Valley wineries and Applegate lake. Snow capped mountains in view most of the year. This space has a private bedroom and bathroom with a separate entrance. For the chilly nights, enjoy a cozy fireplace and a movie.

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Cottage on River Farm -Applegate Wine Trail

Classical cottage on a 5-acre micro-farm, on the Applegate River near vineyards. This cozy cottage on "Red Barn Farm" is 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.

Romantic Retreat w/ Hot Tub & Starlit Massage Room

The Applegate Spa is a top-rated romantic retreat in Southern Oregon’s stunning Applegate Valley. Perfect for couples, it features a private hot tub, cozy fireplace, and a dreamy massage room beneath a glowing starlight ceiling. Surrounded by vineyards, rivers, and charming wineries, this peaceful escape blends rustic charm with comfort and relaxation. Just minutes from historic Jacksonville and scenic trails, it’s the ideal place to unwind, explore, and reconnect.

Plymale Cottage Bed & Biscotti - 2BR, Kitchen, AC

4 Guests, 2 Bed Rm, Sitting Rm & Kitchen, the "Hobbit Rm" with toys, teddy bears and a playhouse. Pet Friendly - One (1) small dog (30lbs or under) house trained. My small back yard is not available for a pet. Our upstairs cottage rate is $135/night. Rates do include city taxes, service & c;eaning fees. Guest entrance has stairs and balcony. Kitchenette and small living. TV available in King room. Air Conditioning