Vacation rentals in Ashland

A covered cedar gazebo provides shaded seating, featuring a table and chairs set on a concrete patio. A gas grill is partially visible, and a playset is located in the grassy area nearby. The space is enclosed by a wooden fence.

4.94 out of 5 average rating, 425 reviews

🌟 🥂 Medford’s BEST 📣 🌟 💕Clean, Modern, Private💕

Simple and clean, with a hidden, private driveway in a safe and secure area of North East Medford. This home is only a few minutes from Rogue Valley International- Medford Airport, plenty of shopping, grocery stores, city transit & local hospitals. Take a short drive to explore Crater Lake, Oregon’s only National Park or head over to Ashland & experience the Oregon Shakespeare Festival. Mountains, lakes & rivers nearby & the Oregon Coast is only 2 hours away. There’s something for everyone here!

Guesthouse in Central Point

A modern kitchen and dining area is highlighted by a wooden table, set with a simple vase of flowers. Ample natural light enters through large windows, while sliding glass doors lead to an outdoor space. Stylish pendant lights provide functional illumination.

4.95 out of 5 average rating, 576 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!

4.98 out of 5 average rating, 492 reviews

A bright living area features a comfortable white sofa and a small round table. Large sliding glass doors lead to an outdoor deck surrounded by trees. Natural light fills the space, highlighting the warm wood tones of the flooring and ceiling.

Guesthouse in Ashland

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

4.98 out of 5 average rating, 674 reviews

A gravel pathway leads to a cozy seating area featuring a wooden bench and surrounding greenery. A beige wall and wooden fence create a sense of privacy, while potted plants add a touch of natural beauty to the outdoor space.

Guesthouse in Medford

Orchard Home Cottage * ~ Private, Cozy, Peaceful *

*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

The exterior of a two-story green house is displayed, featuring a central entrance door framed by white trim. Colorful red foliage from nearby trees enhances the welcoming atmosphere. A clear blue sky provides a bright backdrop to the well-maintained landscaping.

4.81 out of 5 average rating, 119 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.

4.99 out of 5 average rating, 582 reviews

Double wooden doors welcome guests to the entrance, surrounded by potted plants. Light fixtures are mounted on either side, illuminating the entryway. A patterned mat lies in front of the steps, which lead up to the door.

Guesthouse in Ashland

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

5 out of 5 average rating, 165 reviews

A mountain-side home is softly illuminated by warm outdoor lights, creating a serene atmosphere at dusk. The structure features a wooden deck with a staircase leading to the entrance, surrounded by lush trees that enhance the peaceful setting.

Home in Gold Hill

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. Whether you're looking for a getaway, family event, road stop, or retreat - you're welcome here. Pets require PRE-APPROVAL.

The living area features a sleek black entertainment unit with a flat-screen television displaying a serene landscape. A potted plant adds a touch of greenery, while light hardwood flooring complements the bright white walls. An adjacent doorway leads to another space in the home.

4.88 out of 5 average rating, 322 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.

4.87 out of 5 average rating, 101 reviews

Tiny home in Medford

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

An outdoor patio area features a built-in gas grill and a wraparound sectional seating arrangement. A circular fire pit is positioned nearby, with string lights hanging above the space. The surrounding wooden fence provides privacy, enhancing the cozy atmosphere.

4.95 out of 5 average rating, 108 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.

4.99 out of 5 average rating, 177 reviews

An outdoor dining area features a square table with a polished wooden top surrounded by four metal chairs. A decorative lantern sits at the center of the table. Lush greenery and colorful flowering plants are positioned nearby against a slatted privacy fence.

Guesthouse in Ashland

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!

4.91 out of 5 average rating, 237 reviews

A view from under a covered area features two 'Guest Parking' signs flanking a clear sight of the tranquil river surrounded by lush greenery. The manicured grounds include light landscaping with gravel and plants, creating a welcoming entry point to the property.

Home in Gold Hill

Big Foot River Lodge

Come and experience the Pacific Northwest at the fully updated Fantastic River Lodge! This property boasts brand new appliances, furniture, electronics, fishing poles, landscaping, and even a fire table. You won't have to share the property with any other guests - it's all yours to enjoy!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Ashland vacation rentals

Self check-in

Monthly stays

Pet friendly

Laptop-friendly workspace

Air conditioning

Stay near Ashland's top sights

Oregon Shakespeare Festival267 locals recommend

Lithia Park198 locals recommend

Ashland Food Co-op91 locals recommend

Brickroom76 locals recommend

Varsity Theatre56 locals recommend

Standing Stone Brewing Company54 locals recommend

House rentals in Ashland

A covered deck features wooden flooring and three black wire chairs arranged for seating. A glass door provides access to the interior, complemented by two wall-mounted lanterns and large windows that offer views of the surrounding neighborhood.

4.91 out of 5 average rating, 107 reviews

Hillcrest Estates

4.99 out of 5 average rating, 292 reviews

A bright living room features large windows that allow abundant natural light, complemented by a comfortable brown sofa and a cozy armchair. Lush green plants add a touch of nature, while a simple coffee table rests atop a textured area rug.

Home in Jacksonville

Britt Bungalow in the Heart of Jacksonville

A comfortable living area features a gray couch adorned with decorative pillows and a cozy blue chair. A simple white console table is positioned beneath a mounted television, with artwork displayed on the wall. Natural light streams through the window, highlighting the wood-like flooring.

4.84 out of 5 average rating, 242 reviews

Trailer parking, king bed, great for guests/pets!

A neutral-toned living area features a comfortable sofa adorned with decorative pillows, with a coffee table positioned in front. A framed cityscape artwork is displayed on the wall. The open kitchen area includes wooden cabinetry and a dining table with seating for four.

4.89 out of 5 average rating, 223 reviews

Cheerful new 2 bedroom home in cul de sac Netflix

4.91 out of 5 average rating, 136 reviews

A cozy living area features a sectional sofa and a leather recliner positioned around a circular coffee table. Natural light floods through the large window, adorned with sheer curtains. A geometric area rug lays over original hardwood floors, enhancing the inviting ambiance.

Home in Central Point

Lovely Central Point Home w/EV Charger

A spacious living area features a comfortable sectional sofa and a stylish armchair, complemented by a wooden coffee table. Natural light filters through sheer curtains, brightening the space. A woven rug adds texture, while a pendant light provides a warm glow, enhancing the inviting environment.

5 out of 5 average rating, 13 reviews

Fun and Spunky two bedroom home!

4.98 out of 5 average rating, 127 reviews

Secluded mountain retreat, Ashland 10 m., by PCT

4.94 out of 5 average rating, 242 reviews

The entrance features a sleek, modern front door flanked by two small windows. A large potted plant adds a touch of greenery, while the concrete steps lead to a welcoming entryway. The exterior showcases a blend of wood and metal materials, creating a stylish façade.

Home in Grants Pass

777 House

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Dog friendly vacation rentals in Ashland

4.99 out of 5 average rating, 111 reviews

A cozy corner of the cabin features a calm dog resting on a soft bed. A small table holds a welcome sign and a plant, while colorful food and water bowls sit nearby. The floor is covered with natural stone tiles, enhancing the rustic ambiance.

Cabin in Jacksonville

Private & Cozy Treetop Cabin in Historic J-vile

A welcoming nook is created with a decorative corner shelf holding framed art and photographs. A wicker basket contains dog supplies, and a plush dog bed lies beneath a sign reading 'RESERVED FOR THE DOG.' Natural light fills the space from a nearby window.

4.96 out of 5 average rating, 138 reviews

Clean, comfy, pet friendly & fully stocked

A serene view of a rustic barn house set amidst tall evergreens. The two structures are distinguished by contrasting colors: one an earthy red and the other a muted green. A gravel path leads to the buildings, providing a sense of private tranquility.

4.96 out of 5 average rating, 180 reviews

Gorgeous Lakeside HOUSE + Indoor SAUNA!

4.86 out of 5 average rating, 107 reviews

A rustic cabin with a green metal roof sits surrounded by tall trees and lush grass. A stone fire pit is positioned nearby, accompanied by log seating, offering a peaceful outdoor space for gathering.

Cabin in Medford

Woodland Cottage near Jacksonville Dog Friendly

4.95 out of 5 average rating, 389 reviews

A small studio cottage is presented with a light green exterior and a sloped roof. Two red chairs are positioned on a concrete deck, surrounded by planters with greenery. Tall evergreen trees frame the background against a bright blue sky with scattered clouds.

Cabin in Ashland

Studio Cottage near downtown Ashland - Queen Bed!

4.93 out of 5 average rating, 163 reviews

The exterior of the home is presented with a well-kept lawn and landscaped garden beds. A large driveway leads to a two-car garage. A vibrant tree provides a splash of color against the neutral siding of the house, while sunlight filters through the leaves.

Home in Central Point

Ideal & quiet location, 3BR+office, perfectly cozy

4.98 out of 5 average rating, 126 reviews

The cozy cabin is surrounded by vibrant autumn foliage, with a wooden porch that offers seating. A blend of trees provides privacy, and a garden pathway leads toward the entrance, showcasing natural beauty with seasonal colors.

Guesthouse in Medford

Creekside Cabin

Guesthouse in Jacksonville

The cottage exterior is seen from the pathway, featuring a fenced yard for privacy. A covered porch is visible, as well as a concrete walkway leading to the entrance. Lush greenery surrounds the home, enhancing the rural setting.

4.98 out of 5 average rating, 178 reviews

Starthistle Cottage in Applegate wine country

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Dog friendly homes in Ashland

A comfortably arranged living area is highlighted by a brown leather sofa and a round coffee table atop a plush area rug. Natural light filters through sheer curtains, illuminating the space and a decorative fireplace contributes to the serene environment.

4.98 out of 5 average rating, 105 reviews

Charming One

A backyard playground features a wooden structure with a slide and climbing area, surrounded by greenery. A swing set with multiple swings stands alongside. Children can be seen playing, while a dog watches nearby. The space is bathed in natural sunlight, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 60 reviews

Pet Friendly w/ hot tub by town!

4.99 out of 5 average rating, 105 reviews

Chic 4 bed/2 bath house with large yard

4.95 out of 5 average rating, 124 reviews

1930s Queen Anne Historic Downtown Retreat

A patio area is visible, featuring a comfortable seating arrangement with outdoor cushions. Green vines climb the posts of a pergola, while a propane grill is seen in the background. A well-maintained lawn and a storage shed complete the outdoor space.

4.92 out of 5 average rating, 201 reviews

🌟30 DAY-25%🌟PET FRIENDLY🌟PRIVATE🌟FENCED YARD🌟W/D🌟

The entrance features a welcoming front porch adorned with a decorative door surrounded by colorful plants and flowers. A stone pathway leads to the door, flanked by neatly trimmed greenery. A bench offers a cozy spot to enjoy the outdoor scenery.

4.83 out of 5 average rating, 24 reviews

Luxury Home in East Medford

4.85 out of 5 average rating, 13 reviews

A peaceful backyard is enclosed by greenery and wooden fencing, providing privacy. Lush grass covers the ground, complemented by flower beds along the perimeter. Sunlight filters through the trees, creating a serene outdoor space ideal for relaxation or play.

Home in Grants Pass

Sweet Valley Home with fully fenced backyard

A charming craftsman-style home is framed by lush green landscaping and white flowering bushes. The inviting front porch features a wide staircase leading to the entrance, with a combination of windows and gables adorning the roofline. Natural light bathes the exterior in a warm glow.