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Vacation rentals in Ashland

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Quick stats about vacation rentals in Ashland

  • Total vacation rentals

    Explore 320 vacation rentals in Ashland

  • Nightly prices starting at

    Ashland vacation rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 26,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    320 of Ashland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Ashland rentals

  • 4.9 Average rating

    Ashland stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Ashland

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

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Top guest favorite
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, 144 reviews
Top guest favorite
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, 566 reviews
Top guest favorite
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

Explore downtown Ashland in a private carriage house! This home was built in 1884 and is on the property of an historic Victorian. Full kitchen with stove, dishwasher and refrigerator. Pellet stove in the living room as well as wall vented heating. Enclosed yard. Separate bedroom and en suite with a tub/shower combo and washer and dryer. Off street parking. HBO and Netflix included. 10 minute walk to downtown Please note the only bathroom is through the bedroom. Dog friendly - no cats please

4.98 out of 5 average rating, 132 reviews
Top guest favorite
Hotel room in Ashland

Swank Suites | King with Lux Tub

Swank Boutique Suites | King Suite with Soaking Tub | Downtown Ashland Experience detailed hospitality and plush amenities while exploring Ashland. STEPS TO ALL ASHLAND HAS TO OFFER. STAY AND PLAY AT SWANK BOUTIQUE SUITES. 🔹 1 block to grocery store 🔹 2 blocks to Ashland Escape Room 🔹 3 blocks to start exploring all the downtown restaurants 🔹 4 blocks to Growler Guys 🔹 6 blocks to Ashland's Plaza Center 🔹 7 minute walk to Chozu Bath & Tea Gardens 🔹 BIKE & HIKE (ride from your front doo

4.97 out of 5 average rating, 103 reviews
Top guest favorite
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, 517 reviews
Top guest favorite
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, 169 reviews
Guest favorite
Home in Ashland

Beautiful and peaceful cottage close to downtown

Come retreat in our oasis during your stay in Ashland! Charming 1 bedroom, two bathroom home, tucked away from the busy boulevard, with a lovely outdoor space to relax in. Our cottage has a full kitchen, comfortable living space, and a pullout couch that converts to a full size, flexsteel mattress. Upstairs is a beautiful queen size bed with high quality linens, a sitting area, fireplace, and an office space. Each story is 500sf and filled with light from the abundance of windows.

4.9 out of 5 average rating, 175 reviews
Top guest favorite
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, 197 reviews
Top guest favorite
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, 307 reviews
Top guest favorite
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

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

4.97 out of 5 average rating, 325 reviews
Top guest favorite
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.

4.98 out of 5 average rating, 694 reviews
Top guest favorite
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)

4.97 out of 5 average rating, 131 reviews

Popular amenities for Ashland vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Ashland's top sights

Oregon Shakespeare Festival

355 locals recommend

Oregon Cabaret Theatre

78 locals recommend

Varsity Theatre

57 locals recommend

Science Works Hands - On Museum

39 locals recommend

Southern Oregon University

34 locals recommend

Louie's of Ashland

29 locals recommend

Pet-friendly vacation rentals in Ashland

Guest favorite
Guesthouse in Ashland

Neil Creek Cottage

4.93 out of 5 average rating, 161 reviews
Guest favorite
A cozy living area features a leather sofa and a patterned armchair, complemented by a wooden coffee table. A flat-screen TV is mounted on the wall, while large windows allow natural light to fill the space, highlighting the warm wood paneling.
Cottage in Ashland

Charming very well appointed cottage !

4.94 out of 5 average rating, 502 reviews
Guest favorite
Guesthouse in Ashland

The Cedar Cottage - creekside studio

4.93 out of 5 average rating, 214 reviews
Top guest favorite
A wooden deck extends along the riverbank, framed by lush green trees. Two chairs provide seating for relaxation, while flower pots add a touch of color. The tranquil water reflects the surrounding nature, creating a serene atmosphere ideal for enjoying the outdoors.
Home in Gold Hill

Rogue River Retreat

4.97 out of 5 average rating, 300 reviews
Top guest favorite
A spacious bedroom features a comfortable bed with soft linens, accented by orange and neutral pillows. Large windows with decorative curtains allow natural light to flood the room. A wooden table and folding chairs provide additional seating, and a ceiling fan offers air circulation.
Apartment in Ashland

Clean, Stylish Apt w/kitchen. block from Downtown

4.89 out of 5 average rating, 895 reviews
Top guest favorite
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, 144 reviews
Top guest favorite
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!

4.95 out of 5 average rating, 624 reviews
Top guest favorite
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.
Guesthouse in Ashland

Mindy’s Ashland Hideaway

4.9 out of 5 average rating, 202 reviews

Ashland house rentals

Guest favorite
The exterior of a light blue building features multiple stories with large windows and a welcoming entrance. Trees line the front, providing greenery, while flowering plants add color to the scene. The surrounding area shows a well-maintained sidewalk and street.
Home in Ashland

Helman Street Penthouse with a View

4.95 out of 5 average rating, 120 reviews
Top guest favorite
A spacious living area features a light-colored couch paired with a glass coffee table adorned with a floral arrangement. Natural light enters through large windows with sheer curtains, illuminating vintage furnishings and a chandelier hanging from the ceiling.
Home in Jacksonville

Unwind at a Luxury Cottage in Jacksonville's Historic Core

5.0 out of 5 average rating, 257 reviews
Guest favorite
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.
Home in Ashland

Street Level Flat in great Downtown Location "A"

4.82 out of 5 average rating, 143 reviews
Top guest favorite
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, 163 reviews
Guest favorite
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, 156 reviews
Top guest favorite
A historic home with a welcoming front porch is surrounded by lush greenery. White flowers bloom in the garden, adding a natural touch to the setting. The sturdy stone base supports the structure, while a dark roof contrasts with the light-colored exterior.
Home in Jacksonville

Historic 1875 Kitchen House

4.99 out of 5 average rating, 128 reviews
Top guest favorite
Home in Jacksonville

Spa Like Stay at the Britt Bungalow in J’Ville

4.99 out of 5 average rating, 349 reviews
Top guest favorite
A two-story house features a light gray exterior and large windows that provide natural light. A covered entryway leads to the front door, while a garage is visible to the right. Surrounding landscaping includes gravel and minimal greenery, and hills can be seen in the background.
Home in Ashland

The Madrone House, mountain views.

4.92 out of 5 average rating, 141 reviews

Pet-friendly house rentals Ashland

Guest favorite
A bright bedroom features a spacious bed adorned with neutral bedding. A wooden desk and lamp are positioned nearby, with framed photographs decorating the walls. Natural light filters through a window draped with sheer curtains, while a small potted plant adds a touch of greenery.
Home in Medford

Clean, comfy, pet friendly & fully stocked

4.95 out of 5 average rating, 259 reviews
Guest favorite
Home in Medford

Holly House: a Pet-friendly Garden Eco-Cottage

4.9 out of 5 average rating, 124 reviews
Top guest favorite
A warm living area features a brown leather sofa positioned beside a round coffee table with a woven design. Three framed botanical prints adorn the wall above, and sunlight filters through the sheer curtains by the window, illuminating the space.
Home in Medford

Charming Two

4.98 out of 5 average rating, 172 reviews
Top guest favorite
Home in Medford

Luxury Guest House in Charming Old East Medford

5.0 out of 5 average rating, 110 reviews
Guest favorite
A bright living area features a light-colored sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by a cozy armchair. Soft natural light filters through sheer curtains, illuminating the space, while a modern mirror and decorative accents enhance the ambiance.
Home in Medford

Clean, pet friendly, 2-Bedroom Cottage with yard.

4.92 out of 5 average rating, 507 reviews
Top guest favorite
Home in Grants Pass

Mid Century Modern

4.96 out of 5 average rating, 393 reviews
Superhost
A cozy home theater showcases black reclining chairs positioned for optimal viewing. A large projection screen is flanked by plush blackout curtains. A bookshelf filled with movies adds to the entertainment options, while soft carpeting enhances comfort.
Home in Medford

6 king bed real movie theater!! 5star BIG Hot tub!

4.79 out of 5 average rating, 308 reviews
Guest favorite
A spacious dining area features a large wooden table surrounded by six chairs. Natural light fills the room through two large glass doors that open to a deck with forest views. A bowl sits at the center of the table, adding a welcoming touch.
Home in Gold Hill

Hygge Hideaway. A home for rest and adventure

4.98 out of 5 average rating, 239 reviews

When is the best time to visit Ashland?

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Avg. price€125€130€132€141€153€166€155€148€148€147€137€129
Avg. temp5°C7°C9°C12°C16°C19°C24°C24°C20°C13°C7°C4°C

Frequently Asked Questions

  • What are the best places to stay in Ashland?

    Many travelers stay in Ashland’s historic downtown for nearby shops, theaters, and dining. Accommodations around Lithia Park are frequently suggested for those seeking a quieter, nature-filled setting.

  • What are the best things to do in Ashland with kids?

    Families can explore the natural playgrounds and duck ponds in Lithia Park, visit ScienceWorks Hands-On Museum, or attend interactive performances during Ashland’s seasonal festivals. Outdoor trails and ice cream shops are also popular with children.

  • What are some of the best things to do in Ashland?

    Attend a play at the Oregon Shakespeare Festival, wander the gardens and woods in Lithia Park, or explore local art galleries. The city is also known for its wine tasting, artisanal shops, and outdoor activities in the Siskiyou foothills.

  • How is the weather in Ashland?

    Ashland has cool, rainy winters, with temperatures around 33–48°F (0–9°C), and warm, dry summers that reach 59–92°F (15–33°C). Spring and fall bring milder days, making layers and a light rain jacket useful for changing conditions.

  • When is the best time to visit Ashland?

    Late spring through early fall is often recommended for warmer temperatures, outdoor performances, and lively events. The city is known for its festival season, but quieter weeks in spring and autumn draw visitors for milder weather and colorful scenery.

  • What are the best places to visit in Ashland?

    Lithia Park draws visitors with its gardens, streams, and recreational spaces, while the Oregon Shakespeare Festival campus is a center for live arts. The Schneider Museum of Art and local galleries showcase the region’s creative energy.

  • What are some hiking trails in Ashland?

    Explore Lithia Park’s gentle riverside paths, or discover hilly forest routes around the Siskiyou Mountains. Locals also mention Grizzly Peak Trail for its views and seasonal wildflowers.

  • What are some family activities we can do in Ashland?

    Families often explore Lithia Park for picnics and nature walks, engage with interactive exhibits at ScienceWorks Hands-On Museum, or share snacks at downtown cafes and sweet shops. Outdoor performances are frequently suggested in Ashland, especially during warmer months.

  • What are some of the best day trip ideas from Ashland?

    Popular day trips include exploring Crater Lake National Park’s volcanic landscape, sampling wine at Rogue Valley vineyards, or hiking in the Cascade-Siskiyou National Monument. Nearby small towns also have art studios and farmers markets.

  • Are there any pet friendly accommodations available in Ashland?

    Many vacation rentals around Ashland welcome pets, especially those near parks and green spaces. Some hosts provide fenced yards or easy access to walking paths for travelers with dogs.

  • What are some local tips for visiting Ashland?

    Ashland’s downtown is walkable, with many shops, galleries, and dining spots clustered near the plaza. Theaters fill up early for performances, so booking ahead is frequently suggested, and comfortable shoes help with exploring the town’s parks and trails.

  • What is Ashland known for?

    Ashland is known for its vibrant theater scene, especially the longstanding Oregon Shakespeare Festival, and its lively arts community. The city also has scenic parks, historic architecture, and access to trails in the surrounding foothills.

  • What are the best hidden gems to explore in Ashland?

    The Japanese Garden inside Lithia Park is a peaceful retreat, and lesser-known galleries showcase local artists’ work throughout downtown. Quiet forest trails in the foothills around Ashland are also appreciated by those seeking solitude.

  • What are the best foods to try in Ashland?

    Ashland has a mix of locally sourced flavors—expect seasonal dishes highlighting Rogue Valley produce, regional cheeses, and Oregon wines. Bakeries and cafes often feature marionberry desserts and artisanal breads.

  • What should I bring for a trip to Ashland?

    Pack comfortable shoes for exploring parks and downtown streets, along with layers for shifting temperatures. A rain jacket is helpful in wetter months, and many visitors bring a reusable water bottle for outdoor activities.

  • What is the nightlife in Ashland like?

    Ashland’s nightlife is centered around intimate theaters, cozy wine bars, and relaxed music venues. The town has options for live performances, open-mic nights, and local craft beverages in welcoming spaces.

  • What are the most popular events or festivals in Ashland?

    The Oregon Shakespeare Festival runs much of the year and attracts theater fans from many places. The Ashland Independent Film Festival and local seasonal celebrations are also popular, especially in spring and late summer.

  • Are there family friendly vacation rentals in Ashland?

    Ashland has a range of family-friendly vacation rentals, including options with extra bedrooms, kitchens, and outdoor spaces. Many are located near parks or in quiet, residential areas, making them convenient for groups with children.

Destinations to explore