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Places to stay near Oregon Shakespeare Festival

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Top-rated holiday rentals near Oregon Shakespeare Festival

Guests agree: these stays are highly rated for location, cleanliness and more.

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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.
Guesthouse 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.

4.98 out of 5 average rating, 564 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.
Apartment 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!

4.94 out of 5 average rating, 141 reviews
Top Guest favourite
A cozy living area features a gray sofa with a yellow accent chair and decorative pillows on a blue and white rug. A wooden dining table is set for four, and a mirror reflects the space. Bright flowers add a touch of color.
Apartment in Ashland

Downtown 3 Bedroom Upstairs Flat with views "B"

Enjoy a stylish experience at this centrally-located flat. This is a beautiful new 3 bedroom upstairs flat with oak hardwoods floors, granite counters, and new appliances. We offer a cozy living room with a sleeper sofa, flat screen TV, and air conditioning. There is a fully equipped kitchen with stainless appliances, microwave and dishwasher. The dinning room leads out to your own balcony. There are 3 bedrooms with a King, Queen and twin trundle bed. All with smart tv’s and attached bathroom.

4.91 out of 5 average rating, 100 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.

4.97 out of 5 average rating, 514 reviews
Top Guest favourite
A spacious king bed is centered under a unique chandelier, with deep teal walls creating a calm ambiance. A cozy kitchenette area is visible, featuring wooden cabinetry and essential appliances. Light flows through a nearby window, complemented by light curtains.
Apartment in Ashland

Moody Ashland Escape: Luxe Suite, Copper Tub

Welcome to the Premier Suite @ The Matriarch, a historic heritage property in downtown Ashland. This self check-in style accommodations 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 our generous copper tub. The Matriarch is our newest addition to the Swank House family.

4.97 out of 5 average rating, 271 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!

4.95 out of 5 average rating, 164 reviews
Top Guest favourite
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.
Guesthouse in Ashland

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.

4.99 out of 5 average rating, 190 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.
Guesthouse 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.

5.0 out of 5 average rating, 300 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.
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 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.

4.99 out of 5 average rating, 688 reviews
Top Guest favourite
Guest suite in Ashland

RedTail Inn - Red McCall Suite | Sleeps up to 6

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)

4.97 out of 5 average rating, 127 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.

4.98 out of 5 average rating, 144 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.

4.88 out of 5 average rating, 179 reviews

Popular amenities for holiday rentals near Oregon Shakespeare Festival

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Oregon Shakespeare Festival

Oregon Shakespeare Festival

354 locals recommend

Oregon Cabaret Theatre

78 locals recommend

Varsity Theatre

57 locals recommend

Louie's of Ashland

29 locals recommend

Paddington Station

28 locals recommend

The Black Sheep Pub & Restaurant

22 locals recommend

Condo rentals with Wi-Fi

Guest favourite
A spacious living area is furnished with plush leather couches and a coffee table. Natural light enters through large windows, framing views of the mountains. A decorative plant and a photograph on the wall add subtle touches to the inviting space.
Condo in Rogue River

The Executive Suite

4.91 out of 5 average rating, 208 reviews
Top Guest favourite
The open living area features a mix of contemporary furniture, including a light-colored sofa and two armchairs. Large windows allow natural light to fill the space, complemented by greenery from potted plants. A dining area is visible in the background, enhancing the welcoming atmosphere.
Condo in Ashland

Plaza North Penthouse

5.0 out of 5 average rating, 34 reviews
Top Guest favourite
Condo in Jacksonville

Creekside Studio • Walk to Downtown & Britt

4.99 out of 5 average rating, 79 reviews
Guest favourite
A bright and spacious lobby area features soft seating with patterned cushions, complemented by a small side table and a decorative plant. An elevator is present for convenience, and large windows allow natural light to fill the space, enhancing the welcoming atmosphere.
Condo in Ashland

Spacious Modern Condo Walk To Downtown & OSF

4.92 out of 5 average rating, 64 reviews
Top Guest favourite
A spacious living area is furnished with a gray sectional sofa and two light armchairs, arranged around a round coffee table. Large windows provide natural light, highlighting the neutral decor and textured rug. A dining area with a wooden table and upholstered chairs is visible in the background.
Condo in Ashland

Plaza North Suite 201 Alexander

5.0 out of 5 average rating, 75 reviews
Guest favourite
A spacious living area is showcased, featuring a comfortable sofa and armchair arrangement. A large screen is mounted on the wall, displaying a serene forest scene. Soft light filters through large windows, and a modern fireplace adds a touch of warmth to the space.
Condo in Ashland

Plaza North Suite 203 Windsor

4.97 out of 5 average rating, 63 reviews
Guest favourite
The entryway is marked by the number '202' on the door, welcoming guests into a bright living space. A comfortable sofa is positioned beside a small side table, accompanied by decorative vases. Natural light fills the room through large windows, enhancing the inviting atmosphere.
Condo in Ashland

Plaza North Suite 202 Sonoma

4.93 out of 5 average rating, 46 reviews
Guest favourite
Condo in Rogue River

Black Pearl

4.89 out of 5 average rating, 98 reviews

Family-friendly house rentals

Top Guest favourite
A spacious living area is filled with natural light, featuring a large sectional sofa and a plush grey couch. A circular glass coffee table is centered on an orange area rug. The kitchen is visible in the background, enhancing the open layout.
Home in Ashland

Creekside Retreat Close to Town

4.97 out of 5 average rating, 260 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!

4.91 out of 5 average rating, 274 reviews
Guest favourite
Home in Ashland

Beautiful and peaceful cottage close to downtown

4.91 out of 5 average rating, 169 reviews
Top Guest favourite
A cozy log house features a red metal roof and is surrounded by tall trees and lush greenery. The structure showcases a covered porch area and a spacious, welcoming outdoor space. Sunlight filters through the trees, enhancing the serene forest setting.
Home in Ashland

Secluded mountain retreat, 10m. to Ashland, by PCT

4.97 out of 5 average rating, 320 reviews
Top Guest favourite
A comfortable living room is furnished with two sofas and an armchair, arranged around a wooden coffee table. Soft pillows complement the seating. A lamp stands beside a wall, providing light, while artwork adorns the walls, adding a serene touch to the space.
Home in Phoenix

Phoenix Rising

4.96 out of 5 average rating, 182 reviews
Top Guest favourite
The exterior of a chic home is displayed, featuring white siding and a welcoming porch supported by wooden pillars. A neatly landscaped yard is visible, bordered by shrubs and rocks, with a garage on one side. Daylight enhances the inviting appearance of the property.
Home in Medford

Designer Home w/ Chef’s Kitchen

4.99 out of 5 average rating, 162 reviews
Guest favourite
A charming two-story home is framed by lush green grass and mature trees. The exterior features a classic design with a combination of large windows, a welcoming porch, and a tasteful blend of light and dark siding. The sky is bright with scattered clouds.
Home in Central Point

Beautiful Country Home next to Jacksonville!

4.96 out of 5 average rating, 151 reviews
Top Guest favourite
A charming cottage exterior is framed by lush greenery and features a light-colored façade with a teal metal roof. A small porch chair and potted plants are positioned near the entrance, while a white picket fence adds a quaint touch to the front yard.
Home in Ashland

High Street Cottage, Artist's Garden Cottage

4.96 out of 5 average rating, 154 reviews

Apartment rentals with air conditioning

Top Guest favourite
A serene pond surrounded by vibrant autumn foliage reflects hues of red, yellow, and green. The trees frame the water's edge, creating a peaceful natural setting highlighted by scattered leaves floating on the surface.
Apartment in Ashland

The Carriage House, Winner 2025 Best of Ashland!

4.89 out of 5 average rating, 297 reviews
Top Guest favourite
A comfortable seating area is showcased with a vibrant red sofa, accompanied by a white chair. Colorful woven textiles adorn the walls and floor, adding cultural richness. Soft lighting highlights the warm tones of the decor, creating an inviting space for relaxation.
Apartment in Ashland

Mexico Apartment at Wood Hamlet, by Downtown

4.94 out of 5 average rating, 283 reviews
Top Guest favourite
A bright studio suite features a comfortable sleeping area with a neatly made bed. Two patterned chairs are placed in a cozy seating nook, near a small kitchenette area. Light wood flooring complements the warm tones of the walls and furnishings.
Apartment in Medford

Suite Comice EV Charging

4.96 out of 5 average rating, 498 reviews
Top Guest favourite
A comfortable living area features a grey sofa with orange accent pillows and a light purple armchair. A decorative area rug in rich colors anchors the space. Large windows allow for natural light, complemented by vibrant orange curtains and a wall-mounted TV.
Apartment in Phoenix

5 Star Luxury Southern Oregon Suite

4.95 out of 5 average rating, 216 reviews
Top Guest favourite
A cozy living area features a comfortable dark sofa facing a large television mounted on the wall. Two light-colored armchairs are positioned nearby, accented by a small table holding a vase with flowers. Natural light filters in through the window, complemented by a patterned area rug.
Apartment in Medford

Madrona Suite

4.99 out of 5 average rating, 271 reviews
Top Guest favourite
An open studio layout is captured, featuring a kitchen with stainless steel appliances and a dining area with a round table. A spacious bed is positioned near a television mounted on the wall, with a laundry area visible at the back. Fresh flowers are arranged on the table.
Apartment in Medford

"Panorama Place"

4.96 out of 5 average rating, 190 reviews
Guest favourite
A modern living space features a cozy gray sofa and a wooden TV stand. A smart TV is positioned for viewing, with natural light entering through nearby windows. The entry door is white, complemented by a lamp on a side table, creating a welcoming atmosphere.
Apartment in Medford

Peach Street Super Suite

4.89 out of 5 average rating, 184 reviews
Superhost
The studio features a spacious bed covered with a textured white quilt, positioned beside a bedside lamp. A wall-mounted television is visible, displaying a scenic landscape. Artwork adorns the walls, complemented by natural light entering through the door and window.
Apartment in Medford

South Medford Studio Apartment

4.86 out of 5 average rating, 108 reviews

Other great holiday rentals near Oregon Shakespeare Festival

Top Guest favourite
A warm welcome is extended by the cottage's sign, displaying 'Alice Berry Cottage,' positioned beside a red door. A wreath is subtly adorned on the door, enhancing the inviting entrance to this charming residence.
Guesthouse in Ashland

Alice Berry Cottage

5.0 out of 5 average rating, 102 reviews
Guest favourite
A charming yellow cottage is surrounded by lush greenery, featuring a welcoming entrance with a wooden door and a small outdoor seating area. The well-maintained garden highlights the tranquil setting, with a pathway leading to the entrance under the shade of trees.
Cottage in Ashland

ABBOTT'S COTTAGES- Lark

4.93 out of 5 average rating, 160 reviews
Top Guest favourite
A cozy living area features a brown leather sofa paired with a green armchair, arranged around a decorative rug. A flat-screen television is positioned against the wall, complemented by a large window allowing natural light. A potted plant adds a touch of greenery.
Guesthouse in Ashland

Historic carriage house close to downtown Ashland

4.98 out of 5 average rating, 125 reviews
Top Guest favourite
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.
Guesthouse in Ashland

Modern Airy Retreat - Views, Walk to Everything

4.96 out of 5 average rating, 214 reviews
Superhost
The cozy sleeping area features a twin bed adorned with a colorful blanket and decorative pillows. Brightly painted walls in warm hues reflect a sunset, while an air conditioning unit and a small window provide ventilation and natural light.
Tiny home in Ashland

Walk to town! Cozy Forest Teeny House

4.79 out of 5 average rating, 198 reviews
Top Guest favourite
The exterior of the two-story building is framed by mature trees and colorful autumn foliage. A covered porch with railing extends over the entrance, providing a sheltered area with seating. An outdoor parking space is visible, accommodating vehicles.
Bungalow in Ashland

Penthouse Suite, easy walk to downtown.

4.99 out of 5 average rating, 141 reviews
Guest favourite
A historic two-story home with yellow siding is framed by a white picket fence. The front porch is supported by columns, and large windows provide natural light. A manicured lawn is visible, complemented by neatly trimmed bushes.
Home in Ashland

Pioneer Vacation Rentals - Pioneer South

4.92 out of 5 average rating, 62 reviews
Guest favourite
The open living space features large windows allowing natural light to illuminate the area. A cozy blue sectional couch sits on a patterned rug, complemented by a brown armchair and a small side table. A dining area is visible in the background, with a wooden table and chairs.
Home in Ashland

Grandview of Ashland | Hot tub | Sauna | Firepit

4.98 out of 5 average rating, 41 reviews