Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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Guest favourite

Guesthouse in Ashland

4.98 out of 5 average rating, 483 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

4.8 out of 5 average rating, 117 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, 368 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

Cabin in Ashland

4.67 out of 5 average rating, 27 reviews

HOT TUB! Quiet Comfy Cabin at Hyatt Lake Cabin 44

This peaceful 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 Grants Pass

4.96 out of 5 average rating, 208 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!

Guest favourite

Cabin in Ashland

5 out of 5 average rating, 13 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

Apartment 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, 295 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

Home in Medford

4.95 out of 5 average rating, 98 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.

Guest favourite

Tiny homes in Grants Pass

4.96 out of 5 average rating, 105 reviews

River Rapids Home, stargazing from the hot tub!

This stand alone one bedroom tiny home provides all of the amenities of a home, a one bedroom & 1 full bath on the Applegate River only 10 minutes from historic downtown Grants Pass and 5 minutes from the Applegate wine trail. It is about a 5-7 min walk downhill with a stairwell to a secluded private beach oasis. About a 10 minute walk back up to the home. The oasis is amazing… see photos

Guest favourite

Camper/RV in Medford

5 out of 5 average rating, 15 reviews

New Pretty 44' 5th wheel Close!

Enjoy the lovely setting of this romantic spot with beautiful views, pretty kitchen and big TV! Right near Prescott park to hike Roxy ann. Close enough to be about 12 minutes from airport. Water Lily Koi pond on property also. Right cross from Saddleridge, Medford premier neighborhood and a quick drive to Ashland. We also rent another rv on property sometimes.

Guest favourite

Guesthouse in Ashland

4.99 out of 5 average rating, 163 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!