Vacation rentals in Applegate

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Top-rated vacation rentals in Applegate

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Top guest favorite

A spacious living area features a light-colored couch paired with a glass coffee table adorned with a floral arrangement. Natural light enters through large windows with sheer curtains, illuminating vintage furnishings and a chandelier hanging from the ceiling.

Home in Jacksonville

5 out of 5 average rating, 242 reviews

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.

Top guest favorite

The exterior of the modern two-story cottage features a large outdoor deck with steps leading to a landscaped yard. A circular fire pit surrounded by wooden chairs offers a cozy gathering space, while the fenced yard provides privacy and a serene environment.

Farm stay in Jacksonville

4.98 out of 5 average rating, 117 reviews

Cozy Family Ranch Cottage! Near Vineyards & Lake!

Welcome to Guches Ranch! Nestled on a picturesque ranch established in 1964 by the Guches family, a vast expanse of lush farmland. Our Airbnb listing is the ultimate retreat for those seeking solace and serenity away from the hustle & bustle of city life. We are located centrally to local popular Vineyards in the serene Applegate Valley, just 12 miles outside the historic Jacksonville Oregon. Our brand new modern-style single cottage is a stand alone unit & is a private cozy, yet spacious haven.

Top guest favorite

A welcoming cottage exterior is framed by greenery, featuring a charming front porch with seating and flower pots. A gravel pathway leads to the entrance, which has a bright front door and decorative elements enhancing the inviting entrance.

Cottage in Grants Pass

4.96 out of 5 average rating, 268 reviews

Applegate cottage at boutique winery!

Located right in the middle of Southern Oregon wine country. You will be staying in a cottage on a vineyard with our own winery and tasting room onsite. Tasting room open Saturday & Sunday. (April-December) With 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport, Troon, Schultz, Schmidt, Blossom Barn, Rosellas & Solaro just to name a few. Downtown Grants Pass & Jacksonville are 30 minutes away. Highway 5 is 30 min away.

Guest favorite

A cozy studio is nestled among tall pine trees, illuminated softly by warm outdoor lights. The clear night sky is filled with stars, adding a serene backdrop to the natural surroundings. A pathway leads to the entrance, inviting exploration of the tranquil setting.

Treehouse in Jacksonville

4.97 out of 5 average rating, 283 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.

Top guest favorite

The kitchen area features stainless steel appliances including an oven, microwave, and refrigerator. Wooden cabinets and open shelves provide storage and decor. A stone floor adds texture, while light fixtures and potted plants contribute to the bright, welcoming ambiance of the space.

Cabin in Jacksonville

4.99 out of 5 average rating, 139 reviews

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.

Guest favorite

The classic cottage is framed by green foliage, showcasing a welcoming entryway with a black door and a symmetrical window. A bench is positioned on the porch, complemented by flower pots on either side. The gravel path leads to the entrance, surrounded by trees.

Cottage in Jacksonville

4.92 out of 5 average rating, 219 reviews

Cottage on River Farm -Applegate Wine Trail

Classic one-room cottage on a 5-acre micro-farm, on the Applegate River near vineyards. This cozy cottage is a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit (when not in wildfire season) 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.

Superhost

A hot tub filled with clear water is positioned on a private deck, offering panoramic views of surrounding mountains and lush forest. Sunlight reflects off the water's surface, enhancing the tranquil setting, with a glimpse of a river in the distance.

Guest suite in Jacksonville

4.87 out of 5 average rating, 178 reviews

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.

Guest favorite

The outdoor deck area features a private hot tub surrounded by greenery. A colorful tiled table offers seating, and elegant lighting hangs from the red-beamed roof. The space is complemented by a striking black and white patterned rug, creating an inviting atmosphere for relaxation.

Guesthouse in Jacksonville

4.95 out of 5 average rating, 130 reviews

La Petite Maison + Spa

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.

Guest favorite

Four orange Adirondack chairs are arranged on a grassy area, facing a wide, open view of a distant mountain landscape. A clear blue sky scattered with white clouds creates a serene backdrop, while leafy branches frame the scene.

Guest suite in Jacksonville

4.85 out of 5 average rating, 253 reviews

Scenic and relaxing roadtrip stop-over!

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!

Top guest favorite

An outdoor seating area is framed by wooden beams and surrounded by a fenced space. Comfortable chairs and a sleek fire pit create a cozy gathering spot, while tall trees and mountains provide a serene backdrop.

Camper/RV in Jacksonville

5 out of 5 average rating, 112 reviews

Lux roadtrip stop over and stay-cation getaway

Experience your own personal oasis at this beautifully private spot! Rurally located, this nostalgic Airstream will invite you to relax and rejuvenate. Our space is intentionally designed for you to sleep well, eat well and enjoy the surrounding views. The glorious outdoor space has a luxurious outdoor grotto shower with endless HOT water, large covered pergola with propane fire pit, covered dining, and BBQ w/prep space. Privacy surrounds you as you relish in the Applegate Valley!

Top guest favorite

An inviting outdoor patio area is surrounded by greenery, featuring a round table with a floral tablecloth and two green chairs. A large red umbrella provides shade. The cottage's door is framed by a vibrant window box filled with flowers, contributing to a charming ambiance.

Guesthouse in Jacksonville

4.93 out of 5 average rating, 1,108 reviews

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.

Superhost

An outdoor hot tub is illuminated under warm string lights, set within a wooden gazebo. The surrounding area features wooden fencing and lush greenery, creating a serene environment. A soft blue glow from the water contrasts with the warm evening sky, enhancing the tranquil ambiance.

Cottage in Jacksonville

4.94 out of 5 average rating, 431 reviews

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.