Vacation rentals in Jackson County

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Top-rated vacation rentals in Jackson County

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

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Guest favorite

A modern kitchen and dining area is highlighted by a wooden table, set with a simple vase of flowers. Ample natural light enters through large windows, while sliding glass doors lead to an outdoor space. Stylish pendant lights provide functional illumination.

Guesthouse in Central Point

4.95 out of 5 average rating, 576 reviews

The Hygge Stay in the Heart of Southern Oregon

Pet friendly**Close to the I-5 interstate. Within walking distance to park! This guest house, is filled with natural light making it bright and inviting. Thoughtfully designed with guests in mind, you will have no trouble feeling comfortable with all the amenities you’ll need. *Fun fact**, the night stands in the main bedroom were made in the shop downstairs and designed by husband and I! *Airbnb is above working cabinet shop* Message me if you have any questions, I’ll respond within an hour!

Guest favorite

An elevated view displays the spacious great room featuring rustic wooden beams and a cozy seating area with leather sofas. Large windows invite natural light, while the open layout connects to a modern kitchen with wooden cabinetry. A sliding door leads to an outdoor deck.

Farm stay in Days Creek

4.92 out of 5 average rating, 117 reviews

Family Retreat- Barn Complimentary Farm Breakfast

Private House 2 kitchens, fully stocked, 2 Full bathrooms , 4 Private bedrooms,Bonus Kids Loft with 2 Twins 2 kids futons There is a memory foam sofa bed in the family room on one side. This Duplex joins together via a Sliding Barn Door into over 3000 Sq Feet Of Grand Rustic Décor. A great room with 20’ ceilings for gathering after a long day of play. We are dog friendly with plenty room to roam. Enjoy 2 private creek side Decks with views of the farm. We are dog friendly but Do Not allow CATS

Top guest favorite

A bright living area features a comfortable white sofa and a small round table. Large sliding glass doors lead to an outdoor deck surrounded by trees. Natural light fills the space, highlighting the warm wood tones of the flooring and ceiling.

Guesthouse in Ashland

4.98 out of 5 average rating, 492 reviews

Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

Superhost

The exterior of a two-story green house is displayed, featuring a central entrance door framed by white trim. Colorful red foliage from nearby trees enhances the welcoming atmosphere. A clear blue sky provides a bright backdrop to the well-maintained landscaping.

Home in Ashland

4.81 out of 5 average rating, 120 reviews

Street Level Flat in great Downtown Location "A"

This is a beautiful new 3 bedroom flat with oak hardwoods floors, granite counters, and new appliances. There is a laundry room with a washer and dryer. We offer a cozy living room to relax after your busy day with a sleeper sofa, flat screen TV, and air conditioning for those warm days. There is a fully equipped kitchen with stainless appliances, microwave and dishwasher. This flat is located in a prime location, a 5 minute walk to the popular Shakespeare Festival, restaurants and shops.

Guest favorite

An outdoor porch features wooden flooring and a variety of seating options, including a wooden table with four chairs. A plush white dog is seen walking along the porch. Nearby, a cozy throw is draped over a chair, complementing the rustic wooden structure.

Cabin in Ashland

5 out of 5 average rating, 16 reviews

Whispering Pines Cabin near Hyatt Lake

This cozy mountain cabin is located at 5200 feet elevation in the Cascade-Siskiyou National Monument, just 21 miles off the I-5. It is walking distance to Hyatt Lake, the Pacific Crest Trail and 2.8 miles from the Table Mountain Snow Park. This area is perfect for a large variety of outdoor activities such as fishing, paddle boarding, kayaking, hiking, mountain biking, E-biking, dirt biking, ATVs, snow mobiling, snow shoeing, back country skiing, sledding and hunting. NO OUTDOOR FIRES

Guest favorite

The exterior of a spacious cottage is showcased, surrounded by lush greenery and rolling hills. A wrap-around porch frames the building, offering panoramic views of the natural landscape. The property is nestled within expansive land, emphasizing its secluded position atop the mountaintop.

Home in Medford

4.92 out of 5 average rating, 38 reviews

Valley Top Private Oasis

Nestled atop a private mountaintop property, this charming cottage offers solitude and breathtaking views. It has: -one bedroom -well equipped kitchen -cozy living room providing comfort and relaxation. A convenient desk space is also available. Positioned at one of the city's highest points, the cottage overlooks the stunning Rogue Valley, creating an intimate connection with nature's beauty. Escape the bustling world below and find tranquility in this idyllic mountaintop retreat.

Guest favorite

The living area features a sleek black entertainment unit with a flat-screen television displaying a serene landscape. A potted plant adds a touch of greenery, while light hardwood flooring complements the bright white walls. An adjacent doorway leads to another space in the home.

Home in Medford

4.88 out of 5 average rating, 325 reviews

Southern Oregon Gem (EV Charger)

Welcome to our charming little home in Medford, Oregon. a delightful haven designed for comfort, cleanliness, and efficiency. Nestled near the city center, this inviting space offers a perfect blend of coziness and functionality for a memorable stay. The thoughtful layout maximizes every inch of space, creating a welcoming atmosphere for solo travelers, couples, or small groups. The color palette is soothing, creating a serene ambiance that promotes relaxation.

Superhost

A spacious outdoor deck is viewed, featuring a large wooden table and benches. A fire pit made from a tree stump is centrally located, with a grill positioned nearby. Surrounded by tall pine trees, the area is well-lit by natural sunlight.

Cabin in Ashland

4.69 out of 5 average rating, 32 reviews

Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44

This quiet comfy cabin is located at 5200 feet elevation in the Cascade Mountain Range, just 21 miles off the I-5. This cabin is walking distance to Hyatt Lake, the Pacific Crest Trail and 2.8 miles from the Table Mountain Snow Park. This area is perfect for a large variety of outdoor activities. The cabin has a wide variety of amenities including 2 TVs, DVD player, Satellite TV, and WiFi, BBQ and hot tub. The loft ceiling stands at 56" tall.

Superhost

An aerial view of a tiny home interior is displayed, featuring an open kitchen with wooden countertops and a black stove. A cozy seating area is seen with green and white patterned cushions, complemented by steps leading to an upper level. Natural light illuminates the space.

Tiny home in Medford

4.87 out of 5 average rating, 101 reviews

Broken Chair Ranch Bungalow

Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our tiny home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit near the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

Guest favorite

A modern kitchen area features sleek cabinetry, stainless steel appliances, and a streamlined island with a sink. A gas stove is positioned next to a microwave, while a large television is mounted on the wall. Natural light illuminates the space from nearby windows.

Camper/RV in Medford

5 out of 5 average rating, 17 reviews

New Pretty 44' 5th wheel Close!

Right cross from Saddleridge, Medford premier Romantic retreat with stunning views of rolling hills and mountains. Enjoy a pretty kitchen, big TV, and peaceful koi pond—especially lovely in spring. Near Prescott Park for Roxy Ann hikes, just 12 mins from the airport. Across from Medford’s Saddleridge neighborhood and a short drive to Ashland. We occasionally rent a second RV on the property too. We also rent another rv on property so

Guest favorite

An outdoor patio area features a built-in gas grill and a wraparound sectional seating arrangement. A circular fire pit is positioned nearby, with string lights hanging above the space. The surrounding wooden fence provides privacy, enhancing the cozy atmosphere.

Home in Medford

4.95 out of 5 average rating, 109 reviews

Voted Guest Favorite/Fast Wi-Fi/Hiking/Shopping.

Modern millennial dream! Stunning , bright & modern home. If you’re looking for that Instagram worthy spot, look no further! The living area boasts a floor to ceiling hand-painted mural for that perfect family photo backdrop. Each room caters to every age from young to seasoned. The open concept living room boasts a floor to ceiling mural of the mountains and comes complete with a gas fireplace.

Top guest favorite

An outdoor dining area features a square table with a polished wooden top surrounded by four metal chairs. A decorative lantern sits at the center of the table. Lush greenery and colorful flowering plants are positioned nearby against a slatted privacy fence.

Guesthouse in Ashland

4.99 out of 5 average rating, 179 reviews

Courtside Cottage - WalkScore 93 - Dog Friendly

The same cottage you've known and loved. Now we manage it ourselves. A sampling of previous reviews are in the photos. Named one of the Top Ten Traveler's Accommodations in Ashland by The Oregonian. Dogs always welcome. Please read all of the house rules and particulars regarding parking. Thanks!