The bard in you will find a home in Ashland, where Oregon Shakespeare Festival runs annually from February to October. The city of Ashland in Jackson County, Oregon is also a top contender in “The 100 Best Small Art Towns in America.” It’s a city where you can indulge in back-to-back offerings of Shakespeare and non-Shakespearean plays. It’s also a place for culinary delights, road trips, mountain biking, and skiing. There is no shortage of inspiration and adventure in a cultural hotspot such as Ashland. Bring the family or make it your clique’s next fun stop. Lithia Park is a 100-ac (40.47-ha) paradise of gardens, trails, hardcourts, and water features. Will you drink from one of the mineral-rich public water fountains? Think about it while reading about the best vacation rentals in Ashland, Oregon.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 11, 2024.
1. Pet-friendly cottage with a private patio (from USD 298)
A modern cottage awaits four guests who are willing to share a single bedroom and sleeper sofa in this studio rental. This renovated Vrbo has a spacious bathroom and an al fresco dining area. Look forward to using contemporary furniture and kitchen implements. It’s a pet-friendly accommodation, so ask about additional fees and house rules when booking.
This is the perfect getaway for theater fans who also like to visit the taphouse after a splendid show. There’s parking space on an alley behind the cottage, so you can walk to Oregon Shakespeare Festival venues.
Top guest reviews
Amenities & Room:
furnishings are modern and stylish and the bed is exceptionally comfortableit is about the size of a large hotel room but makes very efficient use of spaceHost:
and we really appreciated that it was pet friendlyRead more reviewsLocation:
the cottage is located in a great location and walking distance to parks and downtownthe location is ideal - walk to all restaurants the food market and shakespeare festivalthe location was great due to cafes shops restaurants and a grocery store all within walking distanceour dogs enjoyed walking around the city
2. Updated home in historic downtown (from USD 369)
This century-old house is outfitted with a modern kitchen and elegant dining set while restoring and retaining the original flooring. The formal atmosphere of the living room is softened by quirky throw pillows and floral slipcovers. Other gorgeous decorative elements will also catch your eye. The house has three bedrooms, laundry facilities, and a spacious furnished deck.
Go halfway down the block every morning to a cafe for breakfast if you don’t feel like cooking. There are two parking spaces allotted to guests.
Top guest reviews
Amenities & Room:
good wifi signal we were happy not to have a tvthe house was very charming and comfortable for the 5 of usi'd say it's a better 4-6 person house given the one shower and the small spacessecond bathroom is more like a half bath so shared the shower in first bathroomCleanliness:
the house is clean and well equippedthe house itself was clean and had comfortable furnishings and the host was easy to communicate withHost:
the owner alla was responsive pleasant and helpfulRead more reviewsLocation:
great location for suremy family enjoyed being close to main street and walking distance to the theatereasy walk to restaurants shops & lithia parkloved the location - perfect for walking to plays and into towngreat stay lovely house in a perfect location
3. Craftsman-style rental with a garden (from USD 275)
This luxury Vrbo is elegantly and comfortably designed. Every detail in the interior fits the aesthetic, and no expense has been spared to ensure the comfort and satisfaction of guests. The en-suite bedroom boasts luxury hotel-grade amenities, from the bed itself to the toiletries in a bathroom fitted with a rainwater shower system.
This is a Craftsman-style abode with a covered porch. You’ll find the upscale kitchen lacking for nothing, with its granite countertops, espresso machine, juicer, stovetop and oven, and dishwasher. The living room is a cozy spot with a state-of-the-art entertainment system and expansive views of the surroundings. This terrific house with a lovely garden was given The Ashland Historic Preservation Award in 2014.
Top guest reviews
Cleanliness:
the house is clean beautifully remodeled and tastefully decoratedit is carefully maintained clean roomy and tastefully decoratedvery comfortable and nicely decorated extremely cleanthe decor is lovely and the place is spotlessHost:
our host is helpful and easily reachedhope to return soon especially appreciated the kindness and local advice of owner mrthe owners were very accommodating and the home was clean and well-equippedRead more reviewsLocation:
the location is perfect- right in the heart of town an easy 3 block walk to osfspacious great location for restaurants and the osf welcomingappreciated all the wonderful touches in this beautiful accommodation so close to downtown ashlandclose to the osf theaters and all our favorite restaurantsotherwise the house was amazing great walking to everything
4. Charming retreat with beautiful views (from USD 170)
Perhaps a shaded deck where you can sip morning coffee and evening wine is all you need for a memorable stay in Ashland. This updated cottage sleeps four guests in gorgeously lit interiors. The high ceilings and Craftsman features enliven the space, and the views from the living room are no less enthralling than the views from the deck.
This striking cottage has a full kitchen, two beds, two bathrooms, and bucketloads of charm. You’ll be happy to know this rental is only 10 minutes from downtown.
Top guest reviews
Amenities & Room:
views from the loft bed are lovelybeautiful comfortable cottage in good areait was a beautiful cozy and warm cottageCleanliness:
nice clean cottage with private accessit was clean cozy and comfortableas advertised and beyond a comfortable cottage clean quiet and well equippedthe place was spotlessly clean and well-equipped with toiletries beverages and fresh flowersHost:
margaret was really nice and helpful with any questions we hadmargaret and mark such gracious host made us feel welcome from the minute we arrivedgreat location lovely lay out and wonderful hostmachala was a great host just enough communication that was needed for directions and welcomingmargaret was friendly and prompt with communicationRead more reviewsLocation:
the location is absolutely perfectthe studio was inviting and comfortable in a pretty neighborhood close to osflovely cottage conveniently located close to town the osf and grocery storesa charming cottage in a great location
5. Artistic house in central location (from USD 220)
This Ashland artisan house features splendid detail, from the shelf and wall decoration to the bathroom tiling. Rooms are decorated in different colors, and some rooms feature multicolored walls. The front porch features blue accents, with hanging chimes and a small birdhouse.
This appealing Vrbo is immaculate and is provisioned with high-quality cookware, a washer and dryer, and reliable Wi-Fi. This is an established property that has been refurbished and furnished with a dining area, a full kitchen, and a charming front garden. The owner’s artistic lighting pieces are showcased in this Vrbo listing’s interiors.
Top guest reviews
Cleanliness:
and despite its many intriguing tchtochkes the place is very clean and dust-freehouse was well appointed and very cleanHost:
the hosts were wonderful to work withmori and john are terrific hosts eager to be of help when askedthis is a lean and charming home and john is very nice and communicativeRead more reviewsLocation:
great location and lovely placespeaking of downtown the location of this property is super on point and we were close to everythingthis is a great location with so many restaurants stores and activities in easy walking distancelocation is perfect for all things ashlandgreat location surroundings and a beautiful space
6. Elegant downtown cottage with a hammock (from USD 148)
If you’re looking for a home in Ashland with modern dining and kitchen appliances, antique furniture, and a sizable hammock in the backyard, this rental is just for you. This cottage can be your ideal retreat in the midst of downtown.
This two-story Vrbo lets in light through many windows. It has two full bathrooms and three cozy beds to sleep on. The classic elegance of the living room and the workspace will speak to you. Enjoy the peace and quiet this rental offers with your family and friends, as it can accommodate up to five guests.
Top guest reviews
Amenities & Room:
as others note the yard is lovely and the living room is light-filled and comfortablethe moment we entered the cottage we all felt relaxed and comfortableour dogs were welcomed and we enjoyed the nice yard kitchen and entire placeCleanliness:
the furniture was very comfortable everything was quite clean and there were beautiful plants throughoutHost:
arnica was a very gracious hostthe owner is truly charming: present in the background but unobtrusiveeveryone was very helpful and friendly with advice of places to visit in the ashland areai would definitely recommend this place for pet ownersarnica was very welcoming and communicativeRead more reviewsLocation:
walking distance to town was nicesweet cottage with great locationeasy walk to a park for our dogwe were attending the oregon shakespeare festival and this was a great locationthe landscaping and quiet location provided a true oasis outside
7. The Heritage Suite at Second Street Cottages (from USD 420)
This delightful Vrbo is as close to restaurants and shops as you can get. The house is a turn-of-the-century structure with hardwood floors, elegantly furnished rooms, and an expansive outdoor space. A discerning modern traveler with a soft heart for Shakespeare’s sonnets and plays will enjoy this home.
This vacation home has four bedrooms and three bathrooms. Fine furnishings regale the living and dining rooms. The home cook will find contentment in a state-of-the-art kitchen, while the rest of the party takes it easy on the patio and al fresco area on the front porch.
Top guest reviews
Amenities & Room:
wonderful location & well appointed cottage—everything we needed for a pleasant & comfortable weekCleanliness:
was spotless well equipped and very very charmingvery clean very convenient fit our needsthe home was clean and had everything we needed for our stayRead more reviewsLocation:
location was excellent an easy walk to all attractionswe had a great time here close walking distance to downtown stores restaurants ectnice not to have to figure out where to park all around theater and restaurants are walkable
8. Historic home with a covered porch (from USD 368)
The house was built in 1904 and has been spruced up to become a praiseworthy vacation home. This downtown property stands proud on a well-maintained lawn. Guests will appreciate the renovations made to ensure their comfort.
Everything in the house is updated, including kitchenette appliances, laundry facilities, and three spacious beds. The covered porch is cooled by the breeze, accessible through the French doors. Ask the Vrbo host which wine tasting venue they recommend, and let them know if you need a personal orientation about the local theater scene.
Top guest reviews
Amenities & Room:
the exterior is grand and the interior is updated modern and very comfortableRead more reviewsCleanliness:
everything was so clean and convenientvery clean newly remodeled great for our group of 5 adultswe loved the modern look and the cleanliness of the homethe home is clean very well-maintained and adjacent to my favorite restaurant rubysplease property was clean tastefully decorated and very convenient to the downtown and theatre area
9. Well-furnished cottage with a private courtyard (from USD 250)
Have a great holiday in a Vrbo with two bedrooms, a fully equipped kitchen, a stocked bathroom, and all the towels and linen you require for an extended stay. Watch Netflix while finalizing your Ashland itinerary. Don’t fret about sweat and dirt from your outdoor excursions, because the house also has a washing machine and clothes dryer.
The private courtyard has garden furniture, a barbecue grill, and a fire pit. Park your car through the back entrance. If you’re driving an electric vehicle, a free EV charging station is only a block away. The owner lives upstairs and is within reach if you want to ask for recommendations.
Top guest reviews
Amenities & Room:
pleasant quiet place full kitchen air conditioning and nice water fountain outside the bedroom windowwe cooked several meals in the well-equipped kitchen and slept soundly in the comfortable bedsthe cottage was clean and comfortable with a spacious dual-sink bathroom and conveniently equipped kitchenstacy’s cottage was just perfect for a visit to ashland comfortable and great outdoor space walking distance to theatreswe really enjoyed staying in the cottage it was quiet very comfortable and convienant for all activites in ashlandCleanliness:
everything was clean and cozyit was clean well-equipped comfortable and very convenientwe really enjoyed our four days at this spotless and charming home in ashland over the holidaysher place was clean quite and comfortable (despite the heat wave we hit (appreciated the a/c)Host:
the owner was helpful and very accommodatingshe was very friendly and helpfulstacy was very responsive to questions before and during our visitRead more reviewsLocation:
fantastic location very short walking distance to everything in ashlandreally good location within short walking distance of downtown ashland shopping restaurants and oregon shakespeare festivalsuper cute place and so close to everything we walked to the plays every eveningoh did i mention the location is amazinggreat location lovely home perfect courtyard
10. Beautiful oasis with a koi pond (from USD 183)
This two-bedroom cottage from the 1930s is a standout accommodation in Ashland. This cozy, artsy sanctuary in Historic Downtown District is all yours when you book the property, including the house, patio, decks, and verdant yard. As soon as you arrive, check out the salad mix and fresh herbs in the kitchen. You’ll feel energized immediately. The house also boasts hand-crafted and customized pottery and furnishings.
There’s a fabulous surprise waiting for you in the backyard - an oasis with a koi pond and raised plant beds. The generous host will be happy to recommend the best biking trails in town.
Top guest reviews
Amenities & Room:
high street cottage was immaculate and comfortableit is very peaceful and relaxing with comfortable beds and beautiful views out each windowfantastic areas to grill and do laundrythis was a comfortable cottage quiet and with excellent cooling in this august monthCleanliness:
very clean and brightit was very clean and had all of the things we needed for our 3 night staythe house was light and airy and very cleanthe cottage is immaculately clean charming and in a great location-quiet and private but near everythingHost:
all our hosts have been friendly and helpfulthe owners take great care in presenting this very comfortable cottagethe owners mark and elizabeth were very friendly and easy to work withgreat hosts and a perfect locationelizabeth and mark are gracious fun hostsRead more reviewsLocation:
charming little cottage located in a great locationit is a great location for the shakespeare festivalwalking distance to oregon shakespeare festival and lithia park we'll be backquiet and beautiful neighborhood for walking
See Ashland through a poet's eyes
Seize all the activities and events this city has to offer and stay in a stylish and comfortable home during your visit. Whether you love Shakespeare or not, you can count on Ashland’s Vrbo community to exceed your expectations.
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