119 properties available

Located in Ashland, New York, United States. Downtown Ashland private cottage with garden patio The Silver Frog Guesthouse, complete with a queen bed, fold-out twin couch, kitchen and shower-only bathroom, is set back from the main house and overlooks its own private garden patio. It is located in a quiet neighborhood within a 5-minute walk to downtown Ashland shopping, dining and theatre.After a day of outdoor adventure, recreation or theatre-going, guests may dine indoors or alfresco, plus relax with streaming entertainment, board games or drift back through history with a local novel.

Located in Ashland, New York, United States. Courtside Cottage - WalkScore 93 - Dog Friendly Located just blocks away from the OSF theaters downtown, Courtside Cottage is the perfect place to land on your next visit to Ashland. Park your car and live like a local in the heart of town. You’ll feel right at home with just a two-minute walk to restaurants and boutique shops. The cottage is accessible from an alley on a very quiet residential street and has been fully remodeled with a cozy but modern aesthetic.

Located in Ashland, New York, United States. Luxury condo with king bedroom, two bathrooms, full kitchen. Plaza North is a luxury vacation destination located in the heart of downtown Ashland, just steps to the culinary delights, boutique shops and a short walk to Oregon Shakespeare Festival. The Plaza North Suites set a new standard of architectural and design excellence. The Sonoma Suite features 1 bedroom with a king bed, a spacious full bath and fully appointed modern kitchen, state-o-the-art fireplace and large window with view. Covered parking steps from secured foyer and elevator.

Located in Ashland, New York, United States. 2-story, 3 bedroom modern home with king and queen beds, living room and kitchen. About this spaceOne block from OSF. Enjoy a relaxing getaway at the Pioneer House. originally built in 1904. Up to six guests. Easy access to dining, wine tasting, and shopping. Off street parking is also availableThis spacious two bedroom historic home is fully renovated. Both bedrooms have a king size bed. There is a queen-size sectional sofa in the living room as well. The bathroom includes a clawfoot tub and shower. Large kitchennette, a smart TV with DVR, washer/dryer, and lovely views from the mini-deck

Located in Ashland, New York, United States. 230-Downstairs-Duplex-Private Bathroom-Mountain View Great three bedroom - two bath accommodation in historic, downtown locationWelcome to “The Garden" at the 4Th Street InnThe Garden is located just three blocks from the center of Ashland, including the Oregon Shakespeare Festival Theaters, shops, restaurants and art galleries. Minutes from Emigrant Lake, Golfing, and of course wine tasting.It is one of two separate flats at the 4th Street Inn. It is on a residential street in the historic Railroad District. Guest will be welcome to a spacious 3-bedroom 2 bath with a great view of the Mountains.The Garden:-3 bedrooms, 2 full bathrooms, sleeps up to 6 people-living room, dining area-fully-equipped kitchen-patio w/BBQ-in-unit washer and dryerThe Garden has all the amenities: spacious rooms, hardwood floors, finely appointed furnishings, TV/DVD player, free Wi-Fi, and central air conditioning.The Garden has its own private entrance, deck table and chairs for outdoor dining - as well as

Located in Ashland, New York, United States. New Downtown 3 Bedroom Upstairs Flat with views This is a beautiful new upstairs 3 bedroom flat with oak hardwoods floors, granite counters, and new appliances. There is a shared laundry room with a washer and dryer. We offer a cozy living room to relax after your busy day with a sleeper sofa, flat screen TV, and air conditioning for those warm days. There is a fully equipped kitchen with stainless appliances, microwave and dishwasher. If you are here on business there is wireless internet and a desk. This wonderful new top level condo style apartment has a quaint open floor plan with sliding doors that lead out onto your own balcony for outside dining overlooking the North Hills of Ashland. The master bedroom has a King bed, attached bathroom and smart TV. Second room has a queen bed with smart tv. The third room has a twin trundle bed and smart tv. This home is located in a prime location just a 5 minute walk to the popular Shakespeare Festival. With tons of boutiques, both local

Located in Ashland, New York, United States. 2BR Ashland Retreat: Steps to Shakespeare Summary:**Welcome to The Matriarch Heritage House** Located in the HEART of Ashland. Park your car and walk to all you're looking for in your Ashland getaway. Relax in our 2 giant king bedrooms and sprawl out on the regal leather sofa in our generously large living room. Couples, grab your besties and make the most of your Ashland holiday. Everything you need is steps out the front door. Tastefully designed where Victorian get a modern facelift. Your vacation starts here.The Space:This historical home features 2 beds (kings) each with their own en suite private bathrooms. Both bedrooms/bathrooms are upstairs on the second floor. The kitchen, living room, dining room and 1/2 bathroom are located on the 1st floor. This private home shares the property with two other separate units and the large outdoor grounds are considered shared. The other units on property however, do have their own outdoor spaces so interaction with other guests are limited.

Located in Ashland, New York, United States. Available again in September! Spacious Historic House one block to Town! Please see reviews of our other place: vrbo.com/181670 as we don't have any for this place yet. This is a monthly rental. VERY LARGE (1,190 sq ft) historic home in downtown location in fun neighborhood, two blocks from Festival! Open floor plan, ONE level! Furnished. Wood floors. Very large bedroom with bay window, QUEEN antique bed. Dining room with lovely lighting. Claw-foot bathtub with overhead shower. Office, game table, utility porch, shared laundry room (once a week). Includes all utilities, Wi-Fi, OFF STREET PARKING! Funished in antiques, very comfortable! One block to town in fun neighborhood. Smart television. New heating system and A/C. No pets or smoking. This is a private home, yet it is attached to an antique store that we don’t open and above that is a short term rental. You have a private entrance. There are no shared spaces except the table in the front yard.

Located in Ashland, New York, United States. The Peerless Hotel | Junior Suite #2 | Jetted Tub | Historic District Junior Suite #2 is a cozy, unique, one-of-a-kind space with a queen bed, a private bathroom, and a jacuzzi tub. Relax in the jacuzzi and enjoy the wonderful assortment of exotic furnishings and rich accents. This room is on the first floor of the historic Peerless Hotel, and perfectly located for exploring our town on foot. You will be close to the OSF theaters/shows, Lithia Park, and the plaza. Recharge your inspiration in this eclectic space after a day of exploring all Ashland has to offer!POLICY REMINDERS:- Cancellations: 5+ days before arrival, a full refund minus a $25 cancellation fee will be issued (non-fundable rates excluded). After that, only the cleaning fee will be refunded.- Occupancy Limits: Guests agree to not exceed maximum occupancy stated in the listing. Failure to do so may result in additional per person fees if applicable ($20 per person per night) or up to/including reservation termination.- Pa

Located in Ashland, New York, United States. Downtown Ashland Pet-Friendly Haven Step in from the quiet, tree-lined street to this century-old house updated with all modern amenities. A few short blocks to Ashland Plaza, Helman House boasts two large bedrooms, a king-size bed downstairs and two queens upstairs, two full baths, and a basic kitchen for light & simple meal preparation. Enjoy the bright kitchen nook for your sunny morning coffee or a long soak in the cast iron clawfoot tub that will spoil you with the charm of Old Ashland.Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival, boutique shops, award-winning wineries, and restaurants Ashland is famous for, Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer.Two studio cottages are available separately behind the house off the brick terrace parking, making Helman House perfect for a multi-party getaway.This home has a central heat and AC. There is more than one unit at this propert

Located in Ashland, New York, United States. East Main Ease! Newly remodeled townhome is private, but just a short walk to downtown Ashland. Coffee shop, restaurants, bike trails are all 1/4 away. This unit is updated to offer comfortable beds with fine linens, a beautiful spacious walk-in shower, a fully equipped kitchen for any cook, and an inviting living room with large screen T.V. above a usable wood-burning fireplace. Enjoy a glass of wine or coffee on the private back patio. It's a perfect home away from home. Full washer/dryer on second floor. 1 off-street parking spot is dedicated to this unit. Monthly rental available.

Located in Ashland, New York, United States. Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland Second Spring PropertyWe are excited to announce that our property was given The Ashland Historic Preservation Award in 2014.This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3 bedroom 2 bath home or split into two connecting one bedroom apartments with kitchens, dining areas and living rooms. You can stay at home and entertain or walk a block to the heart of Ashland's shopping and theatre district to dine in its finest restaurants, bars and cafes, enjoy the best of the arts or take a walk in beautiful Lithia Park. TITANIAThis beautiful 900 sq. ft. apartment offers a full state of the art kitchen with stainless steel appliances, granite counter tops, cork floors, an espresso machine, juicer, full eating and cooking utensils, 6 burner stove top and oven, dishwasher and dining area with a table t

Located in Ashland, New York, United States. COZY cottage near Park and Town!! Pine Street Cottage:This is a monthly rental, 30 days or more. This comfortable separate ONE BEDROOM cottage is located on the best street in Ashland! It is a lovely 4 minute STROLL to Lithia Park, town and another 2 minutes to the Shakespeare Festival. It has OFF STREET parking. The cottage is decorated in rustic elegance with crisp cotton sheets in summer and flannel sheets in winter. Snuggle under the down comforter and sleep with the soothing colors and quiet upstairs atmosphere with a view of our GARDENS. Kitchen includes everything you’ll need for cooking, including FILTERED water, ORGANIC COFFEE and TEAS and a view of Grizzly Peak. Living room features a comfortable couch and chair, great VIEWS and LIGHT, and Wi-Fi internet access. There are locally hand-made SOAPS in the bathroom with a SHOWER and BATHTUB. There are always fresh FLOWERS on the table where you will enjoy eating and gazing out the bay window. The town of Ashland, known for the

Located in Ashland, New York, United States. The Peerless Hotel | Junior Suite #5 | Jetted Tub | Historic District Step into a world of elegance and romance in this French-inspired guest room on the second floor. You’ll feel pampered by the luxurious drapes, cozy fabrics, and spacious queen bed. Enjoy the natural light from the windows and the skylight, or dim the lights and relax in the two-person jetted tub. This room is perfect for couples or solo travelers who want to indulge themselves in a charming and comfortable setting. Plus, you’ll be close to all the attractions, restaurants, and Oregon Shakespeare Festival shows that Ashland has to offer! Don’t miss this opportunity to book your dream stay in this beautiful guest room! 🌹POLICY REMINDERS:- Cancellations: 5+ days before arrival, a full refund minus a $39 cancellation fee will be issued (non-fundable rates excluded). After that, only the cleaning fee will be refunded.- Occupancy Limits: Guests agree to not exceed maximum occupancy stated in the listing. Failure to do so

Located in Ashland, New York, United States. Shakespeare Sanctuary: Walk to Downtown Ashland Helman House and Cottages ~ Old Ashland Charm, Short Walk to the PlazaJust a few short blocks to Ashland Plaza on a quiet, tree-lined street you’ll findold-Ashland charm in the Helman House and Cottages. Convenient to themany theaters—including the world-renowned Oregon ShakespeareFestival—boutique shops, award winning wineries, and restaurants Ashland isfamous for, Helman House is a home away from home for visitors eager toexperience all Southern Oregon has to offer.Your reservation will include the Helman House and two cottages (sleeps 10). Updated with all modern amenities, Helman House boasts two large bedrooms, a king-size bed downstairs and two queens upstairs, two full baths, and a basic kitchen for light and simple meal preparation. Enjoy the bright kitchen nook for your sunny morning coffee or a long soak in the cast iron clawfoot tub. Located directly behind the house, each of the two studio cottages feature a king-size bed, sit

Located in Ashland, New York, United States. Nancy's Garden Cottage -1. 5 Blocks to Downtown We are located in the heart of Ashland. Only 1 block from Downtown. Enjoy the open Garden and Great location to all Restaurants, Shops, Theaters and Local Sporting Events. We are 3 blocks from University of Southern Oregon. Full Kitchen,1 Bedroom/Real Queen Bed, dining room, full bathroom with Tub, 2 Large TV's.Outdoor shower. Area to for herbal plants.Bike rental from City of Ashland, New Safeway supermarket and Starbucks on same blockMake sure to enjoy the Fenced in Yard with the Fire Pit to roast marshmellows with family & friends.Smaller cottage available for Rent at $1650 furnished. 31 Day Minimum Rental

Located in Ashland, New York, United States. Pioneer Mega 3 vacation homes offering 8 Bedrooms, 5 bathrooms, laundry, TV, and kitchens. About this spaceThis two-story, modern home has three bedrooms. The primary bedroom has a king-sized bed and the guest rooms each have queen-sized beds. A spacious living room includes a comfortable sofa bed that sleeps two, making this home the perfect location for up to 8 guests. Has a modern, fully appointed kitchen as well as an upper balcony and lower patio. The home has two full bathrooms with shower stall downstairs and jetted tub upstairs. Also includes a smart TV with DVR and washer/dryer.

Located in Ashland, New York, United States. #3 President Hayes @ The Mccall House Boutique Hotel This richly elegant room has handsome bay windows and beautiful views of both downtown Ashland and the Cascade mountain range. Named in honor of President and Lucy Hayes. The Hayes visited Ashland in 1889 and this guest room features a portrait and keepsake memorabilia from their visit. This is one of our larger rooms on the front of the house and has two queen beds with updated bedding in addition to a sunny seating area. Located on the second floor. Nestled in Downtown Ashland and the OSF theaters, this Italianate mansion, built in 1883, offers a bespoke experience with personalized accommodations for each guest suite. Expect private entrances and bathrooms with every suite to ensure maximum privacy and comfort.Expect to indulge in a culinary treat curated by our in-house chef, who serves a delectable brunch every day in the dining room at 8:30 & 9:30, complemented by freshly brewed organic coffee. Check out the breakfast menu our

Located in Ashland, New York, United States. #4 Chaucer @ The McCall House Boutique Hotel This romantic room is named in honor of Geoffrey Chaucer whose portrait adorns an intricate antique stained-glass window separating the bath from the main room. Marble topped furnishings and oversized antiques are at home in this large room with a queen bed with updated bedding, a comfortable seating area. The suite features a private bathroom with both a bathtub and shower.Located on the second floor. Nestled in Downtown Ashland and the OSF theaters, this Italianate mansion, built in 1883, offers a bespoke experience with personalized accommodations for each guest suite. Expect private entrances and bathrooms with every suite to ensure maximum privacy and comfort.Expect to indulge in a culinary treat curated by our in-house chef, who serves a delectable brunch every day in the dining room at 8:30 & 9:30, complemented by freshly brewed organic coffee. Check out the breakfast menu our Chef has prepared for your visit. You can opt for The Che

Located in Ashland, New York, United States. Custom Ashland Home with Fantastic Mountain Views Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.5 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island, custom Italian appliances. One bedroom has a california king with attached master bathroom, the other bedroom has a queen bed with a separate bathroom. Perfect for a couples getaway and great for those visiting Ashland for the Oregon Shakespeare Festival. Wireless internet and Satellite TV.

Located in Ashland, New York, United States. Charming home, w/hot tub, close to downtown Pet-Friendly! Great location, just a short walk to all the amenities downtown Ashland has to offer. This historic home (Built 1905) has all of the charm, it includes: hot tub, outdoor shower, barbecue, outdoor deck with patio furniture, large fenced in yard with play structure, fast wifi, office space with printer and copy machine, a hawaiian themed tiki bar and family room, stereo system with record player. This open 1,500 square ft, 3 bedroom 2 bathroom house sleeps 8 comfortably, all recently upgraded, this property is perfect for family retreats, remote working, or to escape the hustle of life. Featuring one king, one queen, two twin beds, Queen convertible sofa, and two full baths. There is a laundry space with a washer and a dryer, three large screen TV’s, original wood floors, pantry, and all kitchen appliances necessary to cook or bake. Have a family game night, listen to your favorite tunes on a vintage Marantz stereo system, while

Located in Ashland, New York, United States. 1 bedroom, 1 bathroom cottage with sleeper sofa & full kitchen. About this spaceThe Anne Hathaway House has seven bedrooms and seven and a half bathrooms, a huge commercial kitchen, dining room with seating for 12, a living room with a library, washer and dryer, front porch and ample outdoor seating surrounded by garden. Downstairs there are three king bedrooms, and one queen bedroom, each with its own bathroom. There is a sitting room as well! Upstairs there are three more queen bedrooms each with its own bathroom!

Located in Ashland, New York, United States. The Florence Room at Chateau Herbe Relax in the window seat while taking in breathtaking views of classical gardens and mountains beyond. This private room has a private en suite bathroom and a queen sized bed. It is located on the third floor of the chateau.The Property:Welcome to the Florence Room at Château Herbe! A state-of-the art contemporary castle with stunning grounds. The property is located minutes from I-5 and downtown Ashland.Guest access:You will have access to the communal chateau sunroom, library, coffee bar, and patio. Explore the vineyard, gardens, orchards, pond pergola, and classical fountain.During your stay:Please reach out to your host via messenger or phone if you have any questions or concerns.There are other guests and tenants that stay on the property.

Located in Ashland, New York, United States. Luxuriously comfortable & peaceful getaway downtown Ashland, with views. Considering the central location of this little gem, it is amazingly peaceful. There is a long driveway that takes you up to the cottage, nestled in trees, with a lovely view across the valley from the balcony, the deck, or the little fenced yard. Being in downtown Ashland, it is across the street from the Cabaret Theater and a block from Lithia Park, three Oregon Shakespeare Theaters & the Green Show, the downtown movie theater, shops, restaurants, and a comprehensive hike & bike trail system. Southern Oregon University is also just a few blocks away with more art venues to enjoy. Ashland is nestled between 3 mountain ranges also, so there is plenty to explore, including the fruit orchards, lavender farms, and wineries in the valley. After skiing on Mt. Ashland, it is a great place to come back to relax with the fireplace and soaking tub. Besides being clean & safe, I like the few extra luxuries that mak