House holiday rentals in Ashland

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 primary, 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.

Luxury Guest House in Charming Old East Medford

Nested on a great oak-canopied street in Old East Medford’s most charming neighborhood, where leisurely walks and turkeys abound, our professionally designed guest home combines authentic Swiss detailing with distinctive features of new and reclaimed materials. A chef’s kitchen and spa-like bath, complete with a soaking tub, towel warmer, and radiant floor heating, create a luxurious retreat. Perfectly situated to explore Southern Oregon, near wineries and trails, we’d be delighted to host you.

Ashland Haus Retreat - 1 block from downtown!

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom. PA # PA-2017-01160

Cozy Ashland Getaway

This bright two-bedroom ranch features a large bedroom with king-sized bed and a smaller bedroom with a queen-sized bed. The living room is furnished with a couch and two comfy chairs. The gourmet style kitchen comes fully equipped. The fenced yard is perfect for your pup. Enjoy a shaded front porch and a back deck ideal for watching sunsets. Interested guests can also inquire about including our 15-foot trailer in their reservation for an extra charge, which accommodates up to two people.

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Beautiful and peaceful cottage close to downtown

Come retreat in our oasis during your stay in Ashland! Charming 1 bedroom, two bathroom home, tucked away from the busy boulevard, with a lovely outdoor space to relax in. Our cottage has a full kitchen, comfortable living space, and a pullout couch that converts to a full size, flexsteel mattress. Upstairs is a beautiful queen size bed with high quality linens, a sitting area, fireplace, and an office space. Each story is 500sf and filled with light from the abundance of windows.

Hygge Hideaway. A home for rest and adventure

In Scandinavia, "hygge" represents contentment & coziness. Settle into this sun-soaked, mountain-side, madrone forest & valley view home for relaxation on the deck, wine by the fire, & mineral baths. This solar powered home has easy access to outdoor adventures. Options include Laundry, Wood Stove (fire logs avail $), fully equipped Kitchen, & EV Charger. Whether you're looking for a getaway, family event, road stop, or retreat - you're welcome here. Pets require PRE-APPROVAL.

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

Charming house two blocks from downtown Ashland

The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comforts you will need. Cozy beds for sleeping late, a full kitchen with a complimentary coffee bar, a living room for socializing with family and friends, and all the privacy of having the entire property to yourselves. Restaurants, shopping, and theater begin two blocks away. This is the perfect house for your unforgettable Ashland experience.

Rogue River Retreat

A nature lovers retreat on the beautiful Rogue River. Watch osprey from the sprawling cedar deck, fish for salmon right on the river bank, or take a soak in the deep tub, this peaceful cabin you won't want to leave. Located half way between Grants pass and Medford with easy access to the 5 freeway, you can enjoy all that Southern Oregon has to offer. The cabin has one deluxe bathroom and one cozy bedroom that has a king size bed with a water view.

Artsy MCM Guesthouse w/ Spa Soaking Tub

2-Bedroom Guest Home - Perfect Stop-Over on Your Oregon Road Trip - Hot Tub - 2 Queen beds - Luxurious soaking tub - Gas fireplace - Walking distance to The Phoodery! - Private & Secluded - Tucked behind the front house for privacy - 1 mile from I-5 access - 7 miles to Ashland - 7 miles to Medford - Come explore the charming small town of Phoenix, Oregon - Nearby wine country for tasting and exploration