Holiday rentals in Ashland

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Top-rated holiday rentals in Ashland

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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

Top guest favourite

Home in Grants Pass

4.97 out of 5 average rating, 112 reviews

Applegate Stargazer, HotTub, 5acres gated.

(Lookup NEW River Rapids Airbnb across street!) https://abnb.me/s0orTJBkdFb Private hilltop retreat. Electric vehicle Level 2 charging station.. Not shared! HotTub, Views of The Valley are enjoyed from the home & gazebo, fire pit table & grilling area. Gaze at the starry display from this home, 10min. to Grants Pass, 5min. to the Applegate Valley Wine Trail.25min. to Jacksonville.1.5 hours to Coast. This is a new 1 bed 1 bath getaway. Owner not on site. No neighbors, Real heat pump, and A/C.

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.

Guest favourite

Home in Grants Pass

4.96 out of 5 average rating, 375 reviews

Charming Cottage, Walk To Downtown!

Newly remodeled 1910 cottage a few short blocks away from historic downtown! 1 bedroom and 1 loft both featuring brand new queen beds.The cottage is only two miles off of I-5 and within walking distance to some of the best restaurants, bars, and shops downtown has to offer. The living room features a 60in HDTV. The kitchen is equipped with dishes, glassware, pots and pans, a keurig and many other commodities . The Outdoor area includes a grill, picnic table as well as a fire pit. No pets.

Guest favourite

Home in Grants Pass

4.96 out of 5 average rating, 213 reviews

Country home on 2 acres just minutes to town

Gorgeous Rustic Home with Electric Car Charger! Beautifully situated on a spacious and treed 1.98-acre lot near desirable amenities, this 3BR/1BA, 1,440sqft property features tranquil mountain views, a classic cedar exterior, an open floorplan, wood ceilings, and an upgraded kitchen with stainless-steel appliances, gas range, and a breakfast bar. All bedrooms are generously sized. Other features: laundry room, BBQ, huge deck, modern oversized shower, a garden, a hot tub, and much more!

Superhost

Flat in Grants Pass

4.89 out of 5 average rating, 288 reviews

West Park Unit A

Located in the prime spot of the Riverside Park area, this 2-bedroom, 2-bathroom is newly built and designed to impress. The upscale and luxurious atmosphere will leave you feeling right at home. Only a 5-minute walk away from Riverside Park, Fairgrounds, Walking Bridge, and the Downtown Historical District, this location couldn't be any better. Despite its proximity to all these popular attractions, this spot remains quiet and private, making for a truly relaxing stay.

Guest favourite

Home in Medford

4.88 out of 5 average rating, 327 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, 180 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!