Places to stay near Oregon Shakespeare Festival

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Top-rated holiday rentals near Oregon Shakespeare Festival

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Top guest favourite

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.

Guest house in Ashland

Charming cottage, walk to town.

Our guests arrive at The Ashland Cottage and their first words are almost always the same: "It's gorgeous!" That's because the cottage delivers what Ashland visitors want- comfort, charm and a walkable location just 10 minutes from downtown and OSF theaters. Though newly built, the cottage echoes the Craftsman character of our 1920s main residence. As a fully separate house with its own private entrance, it offers spacious living with high ceilings, abundant natural light and inspiring views.

LocationValueLong stay

4.98 out of 5 average rating, 566 reviews

Top guest favourite

A spacious bedroom features a large bed adorned with neutral-toned bedding and decorative pillows. A stylish seating area with a daybed rests opposite a window, providing natural light. Soft wood flooring complements the modern design, while minimalistic artwork and a plant add subtle touches.

Flat in Ashland

Ashland Zen Den

Brand new remodeled and designed downstairs basement apartment on Main St. in Ashland. This space is modern, clean and peaceful. Each bedroom is equipped with high end mattresses, linens, TV, and bath robes. There are plenty of books to read and board games to entertain. Enjoy a short walk to downtown where you will find Lithia park, restaurants, cafes, and shopping! 25 min. drive to mt Ashland and world class MTB. Walking distance to Shakespeare festival. Plenty of beautiful wineries near by!

LocationFamilyQuiet

4.94 out of 5 average rating, 148 reviews

Top guest favourite

The inviting living area showcases a stone fireplace as a focal point, complemented by a wooden mantel. Sunlight filters through large windows, illuminating a seating area with a comfortable chaise lounge and a wooden table. A rich area rug adds warmth to the hardwood floor.

Cottage in Ashland

Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

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4.97 out of 5 average rating, 519 reviews

Top guest favourite

The exterior of a classic two-story home is framed by green foliage, with a welcoming front porch featuring two chairs. A neatly maintained pathway leads to the entrance, showcasing subtle architectural details and original fixtures.

Home in Ashland

Ashland Haus Retreat - 1 block from downtown!

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom. PA # PA-2017-01160

FamilyLocationView

4.91 out of 5 average rating, 278 reviews

Top guest favourite

A charming bedroom features a spacious bed covered with soft linens in shades of blue and cream. An inviting chandelier hangs from the angled ceiling, while a window and skylight provide natural light. A cozy seating area and decorative accents add warmth to the space.

Flat in Ashland

Affordable Luxury- One block to Downtown

Welcome to The Matriarch, a historic heritage property in downtown Ashland. This self check-in style accommodations for our Suite 2, means you have the place all to yourself. Stroll to dinner at one of Ashland's finest restaurants or cozy up in the private outdoor living room. Expect thoughtful local touches and attention to every last detail. Soak in the beauty of bold design as you decompress in the large king bed. The Matriarch is our newest addition to the Swank House family.(#18-243)

LocationValueCheck-in

4.94 out of 5 average rating, 235 reviews

Guest favourite

A spacious outdoor area features a crystal-clear swimming pool adjacent to a stone hot tub. Surrounding greenery and colorful flowers enhance the serene setting. Seating options are available nearby, with steps leading elegantly from the house to the poolside.

Home in Ashland

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

ValueLocationCondition

4.95 out of 5 average rating, 170 reviews

Top guest favourite

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.

Guest house in Ashland

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. NEW: a high speed (240 volt) charger for EVs. You need an adapter.

ValueLocationAir conditioning

5.0 out of 5 average rating, 312 reviews

Top guest favourite

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.

Guest house 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 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.

FamilyLocationGetting around

4.98 out of 5 average rating, 698 reviews

Top guest favourite

Guest suite in Ashland

RedTail Inn - Red McCall Suite | w/ Tesla Station

Oregon Shakespeare Festival Lodging Partner! Book with us for a 20% discount on select seats throughout the season. - Fully restored 1890 farmhouse - Short walk to Oregon Shakespeare Festival theaters - Stroll past coffeehouses, shopping, and restaurants - Sleeps up to 6 guests - 1 Queen room - 1 King room - Fold-out Queen sofa bed - Rainfall tile shower - Full kitchen - Private deck - Has Hot tub - Off-street parking - Tesla charging station (for a fee of $25)

LocationValueQuiet

4.97 out of 5 average rating, 132 reviews

Top guest favourite

A cozy living area features a blue sectional sofa and an accent chair, with a flat-screen television mounted on the wall. A sliding barn door leads to the kitchen area, which showcases modern appliances. Natural light filters through the window, enhancing the spaciousness.

Cottage in Ashland

Sweet Breeze Bungalow

Charming Alley bungalow in the historic railroad district. Walk score of 93. Immerse yourself in the heart of Ashland. 5 min. walk to downtown, an easy 8 min. walk to Shakespeare & Cabaret Theaters. Walk to pubs, restaurants, coffee shops, spa's, markets, movie theater, Lithia Park, Japanese garden and trailheads all within 5-12 mins. Nice bike ride to wineries 15 min away, or a 30 min. drive to Mt. Ashland for skiing, hiking, biking and more adventures.

ValueLocationCleanliness

4.98 out of 5 average rating, 156 reviews

Superhost

The exterior of the Serendipity House features a light-colored facade with a welcoming porch shaded by trees. Garden areas with stone pathways are present, enhancing the home's approachable charm. Large windows allow natural light to illuminate the inviting entrance.

Home in Ashland

Charming house two blocks from downtown Ashland

The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our home has all the comforts you will need. Cozy beds, a full kitchen with a complimentary coffee bar, and all the privacy of having the entire property to yourselves. Please note that a gardener visits once a week to maintain the yard. Restaurants, shopping, and theater begin two blocks away. This is the perfect house for your unforgettable Ashland experience.

LocationFamilyWalkability

4.88 out of 5 average rating, 188 reviews

Top guest favourite

A cozy studio room features a king-size bed with decorative pillows against a deep red accent wall. A small dining table with three stools sits nearby, facing an electric fireplace beneath a wall-mounted television. Light hardwood flooring adds warmth to the space.

Guest house in Ashland

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage was named one of the Top Ten Traveler's Accommodations in Ashland by The Oregonian. Located just blocks away from the OSF theaters downtown, it is the perfect place to land on your next visit to Ashland, park your car and live like a local. You’ll feel right at home minutes from Ashland's main attractions. Please read all of the house rules and particulars regarding parking. Thanks!

ValueFamilyIndoor spaces

4.98 out of 5 average rating, 285 reviews