Holiday rentals in Jackson County

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Top-rated holiday rentals in Jackson County

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

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Guest favourite

Guest house in Central Point

4.95 out of 5 average rating, 580 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!

Top guest favourite

Farm stay in Days Creek

4.92 out of 5 average rating, 119 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 favourite

Guest house 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

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.

Superhost

Home in Gold Hill

4.8 out of 5 average rating, 87 reviews

New - Down By The Rogue River - With Fire Pit

The house offers breathtaking views from almost every room. Enjoy the river view from the dining table as you wake up, sipping your coffee. When you're ready to start your adventure you can head out the back door down to the private river access to take a chance at catching some fish. Then end your day on the deck, barbecuing with family and friends. Located between Grants Pass and Ashland it is minutes away from shopping, dining, theater, rafting, hiking, jet boats, and wine tours.

Guest favourite

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 favourite

Home in Medford

4.88 out of 5 average rating, 328 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

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

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 favourite

Campervan/Motorhome 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 favourite

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 favourite

Guest house in Ashland

4.99 out of 5 average rating, 181 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!