Holiday rentals in Ashland

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Top-rated holiday rentals in Ashland

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

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Top guest favourite

Guest house in Ashland

4.98 out of 5 average rating, 489 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, 106 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, 118 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

4.97 out of 5 average rating, 372 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.

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.

Superhost

Home in Medford

4.8 out of 5 average rating, 117 reviews

Stunning 3 bedroom, hot tub, 3 kings 75"4k stv

This ad is for a full 3 bedroom house. We simply make it smaller by locking the downstairs. You will have full access to the main floor, 3 bedroom 2 bath full kitchen living area, bathrooms. We do Not rent downstairs during your stay, 100% private. Gorgeous tuscan decor, executive kitchen. Balconies, hot tub, views. Stunning 4k Samsung Qled tvs in master, both guest rooms, and Living room. Please inquire on pets, Fee is $30 per night per pet paid after booking

Guest favourite

Home in Medford

4.88 out of 5 average rating, 304 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.

Guest favourite

Guest house in Central Point

4.95 out of 5 average rating, 571 reviews

Stylish & Cozy guesthouse |Hygge vibes in R.V

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! Message me if you have any questions, I’ll respond within an hour!

Superhost

Cabin in Ashland

4.7 out of 5 average rating, 30 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.

Guest favourite

Home in Medford

4.95 out of 5 average rating, 105 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, 170 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!

Guest favourite

Villa in Ashland

5 out of 5 average rating, 8 reviews

Ashland French Country Villa w/ Spectacular Views

Large single level French Country style Villa overlooking Ashland with spectacular views of the Rogue Valley, from Grizzly Peak all the way toTable Rock. Minutes to all of Ashland's amenities,yet very private on almost three acres. Excellent forest walking trails very close by.