Guesthouse vacation rentals in Ashland

The spacious studio features large windows, allowing natural light and showcasing views of mountains. A queen size bed is complemented by sitting areas with a television and coffee table. A dining bistro table neatly fits in the corner, enhancing the open layout.

4.96 out of 5 average rating, 187 reviews

Modern Airy Retreat - Views, Walk to Everything

Enjoy the perfect mix of walkable Ashland and your private, airy, urban hideaway. Set in the historic Railroad District with fabulous cafes, restaurants and shops in the same block and nearby, this modern studio over a detached garage has views of trees or mountains from every window. It's only a 5 minute walk to Downtown and a 10 minute walk to Lithia Park and the Oregon Shakespeare Festival. Should you wish, you could park your car in your dedicated space and not use it again during your stay.

The exterior of The Ashland Cottage is shown, featuring a welcoming sign amidst lush greenery. The cottage’s blue siding and distinctive architectural details are highlighted, while a paved walkway leads to the front entrance, framed by natural foliage.

4.98 out of 5 average rating, 523 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

An airy living space is highlighted by large windows that provide abundant natural light and views of the surrounding landscape. A wooden ladder leads to a loft area, while minimal furnishings, including a cozy sofa and a wooden table, create a serene atmosphere.

4.93 out of 5 average rating, 418 reviews

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

4.98 out of 5 average rating, 722 reviews

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 charming exterior of a vintage guest cottage is highlighted, featuring warm wooden siding and green-framed windows. Soft lighting from hanging bulbs creates a welcoming ambiance, while potted plants and rustic barrels add natural elements to the entrance.

4.92 out of 5 average rating, 168 reviews

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

A spacious bed is neatly made with decorative pillows and a patterned throw. A colorful wall art featuring a whale is displayed above the bed. Light enters the room through glass patio doors, revealing a small outdoor seating area with chairs.

4.95 out of 5 average rating, 109 reviews

Delightful suite in a peaceful neighborhood!

Private entrance! Fully equipped kitchenette and full private bath. Pet friendly with a one time $25 pet fee! This lovely unit has a washer/dryer, Roku TV, Air-conditioned/heated, back patio nook, and sited on a quiet dead end street not far from Rogue River access, shopping & restaurants. Minutes from hiking trails, tennis courts, historic downtown Grants Pass, and a day trip away from several local lakes, Crater Lake National Monument, The California Redwoods, and the Oregon Coast!

Guesthouse in Lithia Park

The entrance to the cottage is framed by a rustic trellis and surrounded by lush greenery. A wooden deck leads up to a white door, providing a welcoming access point. Sunshine filters through the leaves, adding a natural brightness to the scene.

5 out of 5 average rating, 210 reviews

Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. Charging is available for your electric cars in the upper parking area.

The studio features an open layout with a king bed and a cozy seating area. A flat screen TV is positioned near the fireplace. Natural light streams through multiple windows, illuminating the kitchenette and dining area, which are adjacent to a private outdoor space.

5 out of 5 average rating, 154 reviews

C Street Station Cottage

Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

Guesthouse in Jacksonville

An inviting outdoor patio area is surrounded by greenery, featuring a round table with a floral tablecloth and two green chairs. A large red umbrella provides shade. The cottage's door is framed by a vibrant window box filled with flowers, contributing to a charming ambiance.

4.93 out of 5 average rating, 1,111 reviews

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

The exterior of a guest house is shown, featuring a light yellow facade and large windows. A deck with white chairs and a table is visible, surrounded by green grass and landscaping stones. A flowering tree provides shade, complementing the serene outdoor space.

4.86 out of 5 average rating, 116 reviews

Mindy’s Ashland Hideaway

Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

Guesthouse in Lithia Park

A spacious living room is presented with stylish furnishings, including a gray sofa and a patterned area rug. Natural light filters through the large windows. A spiral staircase leads to the loft above, while double doors open to the outdoor space.

4.99 out of 5 average rating, 626 reviews

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 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.

A charming entrance features a bold red door and two red metal chairs situated at a small table, surrounded by gravel and greenery. A modern light fixture is mounted beside the door, adding a welcoming touch to the exterior.

4.98 out of 5 average rating, 199 reviews

Manzanita Cottage

Enjoy staying in this newly-constructed cottage in the heart of Ashland's historic railroad district. Park your car and enjoy all that Ashland has to offer by foot. Easy walking distance to downtown shops and restaurants, OSF, Lithia Park and the Ashland Food Coop. Outdoor enthusiasts can start their mountain biking, running or hiking adventures right from their door. Your hosts can help to point you in the right direction. (Permit #: PA-2018-00531)

Popular amenities for Ashland guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A cozy cabin interior features warm wooden walls and high ceilings. A spacious bed is positioned near a window, providing natural light. A colorful sofa and a small table with flowers enhance the inviting setting. A decorative rug adds texture to the wooden floor.

4.87 out of 5 average rating, 291 reviews

The Peaceful Log Room: 1 Bedroom Guesthouse

4.75 out of 5 average rating, 65 reviews

A living room is presented with a large down-filled sectional sofa and a glass coffee table. A flat-screen TV is positioned on a wooden stand, complemented by a decorative lamp. Sliding glass doors open to a view of the garden, allowing natural light to fill the space.

Guesthouse in Gold Hill

Dream Cottage on the Rogue River

A covered patio is framed by vibrant greenery and features a round table with two chairs, along with a lounge chair. Blue doors lead into the cottage, while stone walls provide texture. The area is brightened by natural light streaming under a partially cloudy sky.

4.81 out of 5 average rating, 460 reviews

Carter Lane Cottage

The kitchenette features vibrant blue cabinetry and a wooden countertop. Equipped with a two-burner gas stove, refrigerator, and various cooking utensils, it offers a functional cooking space. Open shelving displays decorative items and kitchenware, enhancing the practicality of the area.

4.98 out of 5 average rating, 51 reviews

Close to Downtown Grants Pass Everything you Need!

A charming building features warm wooden siding accented with unique artwork, including tools and crafts, mounted on the exterior. Large windows and a distinct triangular roof shape enhance its rustic appeal. A gravel pathway leads to the entrance, surrounded by landscaped greenery.

4.98 out of 5 average rating, 427 reviews

Laurel Farm's Guesthouse

4.92 out of 5 average rating, 73 reviews

Chic & cozy 1 bedroom Guest-house

4.92 out of 5 average rating, 13 reviews

The Nest at Highcrest

5 out of 5 average rating, 34 reviews

Adorable guest house with hot tub.

Guest house rentals with a patio

5 out of 5 average rating, 14 reviews

A serene sunroom is presented, featuring two woven seating arrangements with floral cushions. Natural light floods the space through multiple windows adorned with blinds, framing views of the surrounding greenery. A potted flower arrangement adds a touch of color to the warm wood flooring.

Guesthouse in Talent

1910 Orchard Guest House

A cozy bedroom is showcased, featuring a spacious bed with neutral linens and decorative pillows. A small bench with a basket holding folded towels is positioned near the entryway. A hanging rod with garments can be seen in the closet area, along with a plant adding a touch of greenery.

5 out of 5 average rating, 59 reviews

The Peach Pit Inn! A sunny retreat w self check-in

A cozy sitting area features a bay window with natural light flooding in. A plush blue chair is paired with a green cushioned bench and a glass coffee table. A bouquet of flowers adds a pop of color, complemented by a mounted television displaying serene landscapes.

5 out of 5 average rating, 25 reviews

Hanna's House by WanderLodges |1 block to downtown

Guesthouse in Jacksonville

The outdoor deck area features a private hot tub surrounded by greenery. A colorful tiled table offers seating, and elegant lighting hangs from the red-beamed roof. The space is complemented by a striking black and white patterned rug, creating an inviting atmosphere for relaxation.

4.95 out of 5 average rating, 131 reviews

La Petite Maison + Hot Tub

A serene riverbank is framed by tall trees, with sunlight filtering through the leaves. A neatly maintained lawn extends toward the water's edge, where smooth stones line the bank. The reflective surface of the river complements the lush greenery, enhancing the natural beauty of the environment.

4.96 out of 5 average rating, 80 reviews

Spectacular Rogue River views & charm!

5 out of 5 average rating, 14 reviews

The Sunflower Cabin features a red exterior adorned with green vines, nestled among trees. A gravel pathway leads to the entrance, surrounded by natural landscaping. The cabin's roof is metal, adding to its rustic charm while harmonizing with the serene, wooded environment.

Guesthouse in Talent

Sunflower

5 out of 5 average rating, 14 reviews

Peaceful Countryside Stay with Scenic Views

The serene riverbank is lined with lush greenery and tall trees, gently swaying in the breeze. Sunlight filters through the leaves, reflecting softly on the tranquil surface of the Rogue River. A small lawn area invites relaxation, with scenic views of the surrounding nature.

4.96 out of 5 average rating, 74 reviews

New Modern Cottage on the Rogue

Guest house rentals with a washer and dryer

Superhost

A spacious living room area is highlighted by a brown leather sectional sofa accompanied by two decorative pillows. A light wood coffee table sits in the center, situated on a warm-toned wooden floor. Open doorways lead to other rooms, enhancing the airy feel.

4.94 out of 5 average rating, 612 reviews

The Hygge Stay in the Heart of Southern Oregon

A cozy living area features a blue sofa adorned with colorful pillows, situated next to a wooden coffee table. A wood stove provides warmth, complemented by large windows draped in floral curtains, allowing natural light to fill the space. A staircase spirals elegantly in the background.

4.98 out of 5 average rating, 255 reviews

Sand Creek Cottage

A cozy living area features a plush beige sofa adorned with decorative pillows. A small round table is centered on a patterned rug. A TV is positioned on an ornate stand near a window, which allows natural light to brighten the space. A work desk and additional decor complete the room.

4.95 out of 5 average rating, 122 reviews

JJ's Loft | Downtown | Large Deck | Kitchenette

A light-filled living space features a comfortable gray sofa adorned with decorative pillows and a wooden coffee table. A stylish chair is positioned nearby, and a dining area with a round table is visible in the background. A staircase leads to the upper loft.

4.92 out of 5 average rating, 167 reviews

Modern Guest House w/ Hot Tub, Loft & Fenced Yard

A cozy bedroom features a queen size bed, topped with a white duvet and decorative pillows. Two bedside tables with lamps are situated on either side. Natural light filters in through the window, enhancing the serene ambiance of the space.

4.99 out of 5 average rating, 115 reviews

1 BDRM Cottage-Keyless self check in-Quiet Lane

An entryway is visible, featuring an open door leading to the outside and a black garment rack with clothes hangers. Two wooden stools are positioned at a small table, alongside dining ware. A bathroom is partially shown through a doorway, and a glimpse of green grass and a fence is visible outside.

4.95 out of 5 average rating, 426 reviews

Modern, pet-friendly, private - EV charger level 2

Superhost

A cozy living room is presented, featuring a dark grey sofa, a small round black table, and a textured pouf. A woven rug with warm tones adds a decorative element. Natural light filters through large windows adorned with simple white blinds, highlighting a plant and wall decor.

4.78 out of 5 average rating, 130 reviews

East Main Downtown Bungalow "C"

A cozy cottage features a welcoming front porch with two colorful chairs. The vibrant yellow exterior is complemented by large windows, allowing natural light to enhance the cheerful atmosphere. A small, decorative sun emblem is positioned above the door, inviting guests into the space.