Vacation rentals in Jacksonville

Unwind at a Luxury Cottage in Jacksonville's Historic Core

Enjoy your stay at "The Laundry" a lovely historic home. Remodeled and professionally decorated in French Country Chic style with luxury Italian Frette sheets, Turkish towels, robes, slippers, enchanting landscaping with two private fountains and outdoor eating! Ample onsite parking with complete privacy! Two flat screen SMART WIFI TV's with Cable and WIFI/Internet provided, desk/work area along with fun games. A washer/dryer with soap supplies is provided for your convenience. A fully stocked kitchen with stainless steel appliances and gas range. Cuisinart coffee pot with Starbucks coffee and tea provided. You will have access to the entire home. Approximately 1250 sq. ft. with high ceilings. For your comfort the bedroom has a large king size BeautyRest Black mattress with feather-bed topper, Italian linens and Hungarian down pillows. The living room has a large deep couch with feather stuffing. Couch is also a Queen size sofa sleeper that can comfortably accommodate 2 adults. We offer self check-in but I live only 5 minutes away from the cottage. We're happy to help answer questions :) This property is in the core of historic Jacksonville, very conveniently located close to quaint shops and restaurants. Explore hiking trails, try wine tasting, and take an easy day trip to Crater Lake National Forest for a nature fix.

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, living room with a fireplace and an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, & the Britt Pavilion.

Creekside Studio • Walk to Downtown & Britt

Quiet, private studio designed for easy, relaxing stay. Self check-in, dedicated off-street parking, private entrance, queen memory foam bed plus pull-out sofa. Complimentary coffee bar with freshly ground local coffee and curated snack basket. Perfect for couples, solo travelers, remote workers, girls' trip. Kitchenette is ideal for light meals. Includes window workspace, Smart TV, fast Wi-Fi, books, and games. Shops, restaurants, hikes, wine tasting, and groceries within a short walk.

Historic 1875 Kitchen House

Easy walking distance to Britt concert venue, trails, and downtown. The base rate is for the entire first floor and includes one bedroom with en suite bathroom with a large clawfoot tub. Upstairs attic space can also be rented for an additional fee, which includes 3 beds and a full bathroom. Declare 3 guests if 2 people need their own suites. If you are checking in with 4 or 5 people, please indicate the true number of guests, which adds an extra fee per person to cover cleaning costs.

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.

La Petite Maison + Hot Tub

Welcome to La Petite Maison! Come take it easy at our unique and tranquil home away from home. Located in the heart of the Applegate with nearby wineries and exquisite views of the mountains. Our guest house is equipped with 1 master bedroom, full kitchen/bath, dining and living room with and private SPA on your very own deck! Only a 10 minute drive from the historic town of Jacksonville. At La Petite Maison you will have the peace and quiet of the country, and all that you may need.

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.

B.F. Dowell House | Walk to Britt & Downtown

Experience one of Jacksonville’s most iconic historic homes. The beautifully restored 1861 B.F. Dowell House blends original stained glass, marble fireplaces, soaring ceilings, and exposed brick with modern comfort. Located on a large corner lot across from the market and steps from downtown, Britt Festival, restaurants, and tasting rooms. Features private baths for every bedroom, an adjustable Tempur-Pedic bed, clawfoot tub, full kitchen, porch, patio, garden, and lawn.

Charming 2BR Carriage House Outside Jacksonville

Nestled on the historic Bybee Estate, this charming carriage house offers a peaceful retreat just minutes from Jacksonville, OR. It features two elegant bedrooms with ensuite baths, one with a classic clawfoot tub. The gourmet kitchen, spacious dining area, and cozy family room provide comfort and charm. Step outside to a serene backyard perfect for relaxing. Close to wineries, shops, and dining, this is the ideal getaway for history lovers and wine enthusiasts alike

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.

Cottage A in Jacksonville is a great getaway

The C Street Cottages are located in historic Jacksonville. These cottages are in the center of town where walking the streets is a step back in time. The area is also known for great wineries & outdoor activities. Each cottage has a king bed w/ upgraded linens, couch, coffee bar, mini fridge, full bath, TV & wifi, & a private patio space for enjoying that morning cup of coffee or afternoon glass of wine. Your own private oasis!

The Monarch - Luxury Studio W/On-Site Parking

Stay in the heart of historic Jacksonville—just 1/2 block from shops, dining, and wine tasting. This fully renovated single-level studio features vaulted ceilings, a luxurious king bed, kitchenette, dining space, and stackable washer/dryer. Indulge in the spa-like bathroom with a walk-in shower and soaking tub. Enjoy on-site parking and high-end finishes, all steps from the charm of this preserved Gold Rush town.