119 properties available

Located in Ashland, New York, United States. 2 units with 6 bedrooms, 6 bathrooms, a kitchen and large dining area. About this spaceThe house has five bedrooms, each with its own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace, flat screen television and plenty of seating. The house has a large patio. The Cottage has a separate entrance and is one bedroom and one bath and has a futon in the living room to accommodate two additional guests. there is a kitchen with a microwave, refrigerator and range. There is a large private parking area that can accommodate up to four cars.

Located in Ashland, New York, United States. Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3 You have arrived and are now adjacent to 93- acre Lithia Park and downtown Ashland. Within a 5-minute walk, you will discover exceptional restaurants, the Oregon Shakespeare Festival, curio stores, bakeries coffee houses, cafes, bookstores, 4-screen art house movie theater & summer Saturday Farmer's Market. Within a 10 minutes walk enjoy the Food Co-Op, nature shops, pet stores, veterinarians, yoga studios, gyms, the Carnegie-Melon library.Private studio includes kitchen, large desk, bathroom, small sitting area. Adjacent to Lithia Park in Ashland Oregon. Self-contained and independent ductless mini-split heating and cooling system in the room. Radiant floor heating. Kitchen has all amenities and utensils; coffee maker, oven, microwave, electric tea kettle, ice maker. Exceptional lighting. Very quiet. All new construction. Shared washer/dryer.

Located in Ashland, New York, United States. Adjacent to downtown Ashland and Lithia Park. Lithia Park Cabin Arrive. Park your car. Exhale & walk for the remainder of your visit. You are now adjacent to 93- acre Lithia Park and downtown Ashland. Within a 5-minute walk, you will discover exceptional restaurants, the Oregon Shakespeare Festival, curio stores, bakeries coffee houses, cafes, bookstores, 4-screen art house movie theater & summer Saturday Farmer's Market. Within a 10 minutes walk enjoy the Food Co-Op, nature shops, pet stores, veterinarians, yoga studios, gyms, the Carnegie-Melon library.Perfect for someone who appreciates the convenience of being downtown & the feeling of living in the woods, or for a couples retreat, writer's get away, thespian devotee refuge, outdoor enthusiast rejuvenation spot. Lithia Park Cabin is adjacent to 93-acre Lithia Park. Arrive and stroll to OSF, curio stores, bakeries coffee houses, cafes, bookstores, 4-screen art house movie theater, Saturday Farmer's Market, Food Co-Op, nature shops,

Located in Ashland, New York, United States. A Farmhouse Retreat 5 bedroom one story house located on this 10 acre country property, 10 minute drive to town. In a neighborhood of many wineries, vineyards, and hay fields. NO DOG Allowed. Owner highly allergic.Rates shown are for up to and including 8 guests ($45 fee per person per night for each person over 8 guests). Main house: Spacious 5 bedroom, 3 full bath, one-story farmhouse, Master has king bed, and is on one end of house off of great room. All other bedrooms are on other side of kitchen down one hallway going towards garage. Two bedrooms have a queen bed, one room has twin beds, and 5th bedroom has two double beds plus twin. Additional information: House sits adjacent to hayfield with views of the town of Ashland, vineyards and the Siskiyou mountains with Mount Ashland Ski Resort. Ten minute drive from theaters, markets, restaurants and Shakespeare theaters. 40 minutes to Mt. Ashland Ski Resort and there are many local hiking trails including Pacific Crest

Located in Ashland, New York, United States. Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek! You will be an easy 10 minute drive from Downtown Ashland and feel like you are out in the country. The home is 1200 square feet, was built in 2012 and remodeled in 2022. There is ample natural light and 15+ foot ceilings in the living space. Emigrant creek is a year round creek that borders the 8 acre property and is a lovely spot to relax.

Located in Ashland, New York, United States. Updated 3BR Escape: Valley Views, Pet-Friendly Summary:Welcome to The Crest. Entirely renovated, fully stocked, well appointed, midcentury modern home located on a private drive with soaring expansive views of the valley. The open floor plan lends itself to group meals, family game nights, and long conversations around the huge kitchen island. Cozy up in the living room to watch a flix, or face the large windows for expansive views of the Ashland hillsides. Outdoors, discover ample patio seating, BBQ and unmatched views of PNW sunrises. (#18-243)The Space:The Crest is a 3 bed, 1 bath newly renovated mid century modern house that sleeps 5. There is additional sleeping on the couch, which is as wide as a full size bed, to accommodate a 6th person. The large living room is spacious and comfortable with plenty of seating and hangout space. Enjoy the large flat-screen TV, open floor plan, to easily allow all to comfortably enjoy each other's company. Take advantage of the large chef's kitc

Located in Ashland, New York, United States. Mt. Ashland Homestead's Secluded Forest House, 15 minutes from Ashland Beautiful, large architectural home nestled in the Siskiyou/Cascade mountain forests of Southern Oregon. About 15 minutes to downtown Ashland, 20 minutes to Mt. Ashland Ski Area and alpine hiking, and a five minute walk from the house to the Pacific Crest Trail with meadows, forest and ridges looking out to many mountain ranges. This home is a peaceful, quiet, and beautiful getaway: close enough to Ashland to be convenient, yet completely secluded and private. Features include garage, fully equipped kitchen and dining (both formal and informal), two large, open living rooms, large sun room and two-person ofuro hot tub overlooking the forest, seasonal sauna, and walking trails. If you would like a full-size crib and high chair, please let us know. Families and couples often spend weeks here, working remotely and enjoying nature during all the seasons. Professional companies have also found it a beautiful

Located in Ashland, New York, United States. Comfortable, Private Guest Lodging Excellent value, suite in building separate from the house. Comfortable, spacious, clean with high-quality queen bed, pull-out couch, bathroom with shower, mini frig. 3.2 miles from the Ashland Plaza and Oregon Shakespeare Festival, and 1 mile from trailhead access connecting to more than 50 miles of mountain hiking trails.We built the guest suite for family visitors and the guest accommodation is perfect for single travelers, couples or up to three guests. You'll find a high-quality queen bed, a pull-out couch, sitting chair, a mini-refrigerator, and microwave. The unit has heat and air-conditioning, a 32" flat screen TV with HD ROKU and good WiFi --- in the room and throughout the property. There's a small bathroom with stall shower, stocked with towels, shampoo, conditioner and a hair dryer. Bedroom linens and bathroom towels freshly laundered for each visit.Children and well-behaved dogs are welcome; there is an increased ($15) cleaning fee for do

Located in Ashland, New York, United States. The Hux- Make Memories in Ashland Summary:Features for Unforgettable Family Memories:--4 bedrooms; 3 king, 1 queen, 2 twin--Game Room foosball, darts + MORE!--Dedicated LEGO Room--Full kitchen; with local coffee--Porches with lounge seating and dinning--Washer and dryer--2 1/2 bathrooms; luxury toiletriesThe Space:Bedroom 1: King primary bedroom with en suite located on the first floor. Walk in double shower head. Jetted bath tub. Private outdoor entrance to patioBedroom 2: King located on first floorBedroom 3: King with twin. Located on second floorBedroom 4: Queen with twin. Dedicated LEGO room with solar/galaxy theme. Located on second floor.Open Floor Plan: The large, open floor plan is designed for maximum family interaction, providing plenty of seating for everyone to gather, relax, and create lasting memories.Dedicated LEGO Room: A unique bedroom features a dedicated LEGO room, perfect for inspiring creativity and fun for all ages.Game Room: Enjoy endless entertainment in the ga

Located in Ashland, New York, United States. Luxury Ashland Mountain Escape: Pool, Hot Tub Summary:Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfect for group getaways or small gatherings.Take in views of Grizzly Peak while fishing in the small stocked pond, or soak in the seasonal outdoor pool or hot tub while enjoying the quiet of nature.Play games on the lawn, read by the living room fireplace, or try your hand at the billiards table. The kitchen is fully equipped to live out all your entertaining dreams, and a screened sun porch provides the perfect setting for late afternoon noshes and nibbles. A Swank House property.The Space:THE SPACEJefferson Estate is a four bedroom, single-level home that’s ideal for family getaways, girls’ weekends, book clubs, weddings, and reunions. Twelve people sleep comfortably, and sleeping pads are available for crashing by the gas fireplace or out on the screened patio.The generous open living spaces welcome you and your guests to r

Located in Ashland, New York, United States. Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups. Driving through the front gates you will find this Gorgeous and Stunning, completely refurbished, updated farmhouse originally built in 1860. This home and property have been painstakingly refurbished and decorated over a two year period by the Owners. Situated within a working ranch, take a step back in time, with all of today's modern amenities. Huge area to play and roam about the outside of the home. One of Jackson county's oldest, iconic barns in the distance, on the property, provides a great back drop for photo opportunities! surrounded by beautiful hills and mountains. Inside is spectacular with 5 beautiful bedrooms and 3.5 baths. The Owners purposely kept the old farmhouse feel, while updating every inch of the 4500 square feet. fully updated and functional kitchen as well as a huge game room with a full size pool table as the centerpiece, Foosball table as well! 7 large Flat screen TV's throughout

Located in Ashland, New York, United States. Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn Pilot Rock Cabin comfortably sleeps six with a king bed on the main floor and two full sofa beds up in the loft. Meal-making is a snap with an easily accessible, fully stocked kitchen with all the modern amenities including a full oven, built-in microwave, refrigerator, dishwasher, coffeepot, and plenty of counterspace. The six-person table is perfect for dinner or game nights. The cozy wood-burning fire will get you nice and toasty for a deep sleep in the comfortable beds.
A note about our location: We are located 17 miles east of Ashland, about a 25-30 minute drive on Highway 66 which winds up a mountainside. The drive is stunningly beautiful, but we want to make sure guests know that we are not located inside Ashland city limits.

Located in Ashland, New York, United States. Serene Family, Cottage-minutes to Downtown Summary:--> 4 miles to OSF Theatre--> 1/2 mile to Golf Course-->Pet Friendly (fully fenced)Crow's Cottage is a cozy, comfy place to land for your Ashland vacation. This newly built, European style cottage, is located on 5 acres in Ashland and just a few minutes drive to the center of town. King bed and twin-over-QUEEN bunk for room to stretch as you unwind. Huge outdoor deck awaits. Washer and dryer, full size kitchen, comfy living room and plenty of bathroom storage. Inquire about long term stays.The Space:This comfy cottage is detached from the main family home but is attached to our workshop/garage. We are owners of a boutique hotel and luxury vacations homes and this little cottage is located on our family property. We believe that a stylish, functional environment plays an important role in our lives and we created this space to reflect the simple and beautiful home. We have included all the necessary amenities to ensure a comfortable st

Located in Ashland, New York, United States. Lodge Room 4 with Jacuzzi Tub at Green Springs Inn Located in the main lodge of the Green Springs Inn and Cabins, this downstairs private room offers the coziest accommodations with a PNW flare. Enjoy a queen-sized bed next to an in-room Jacuzzi tub. Amenities include mini-fridge, microwave, and coffee maker for simple meal prep. Furry friends (dogs) are welcome to join you as step outside to explore the rolling trails of the Cascade Siskiyou National Monument.Green Springs Inn is nestled on over 100 acres in the Cascade-Siskiyou National Monument. Our nature-immersive micro-resort is tucked away in one of the most biologically diverse areas in North America. We take land stewardship seriously, and we know you do too. Please respect the land and thank you in advance for following all of our rules. We have these rules to protect the land, ourselves, our guests, and our community.Please be advised that all guests will be asked to sign a rental agreement that governs the terms of the stay

Located in Ashland, New York, United States. Lodge Room 7 at Green Springs Inn Lodge Room 7 ~ Green Springs Inn Located in the main lodge of the Green Springs Inn and Cabins, these private rooms offer comfortable accommodations with Pacific Northwest style and everything you need to make your stay extra special. This PET-FREE, private room has two queen-sized beds and features an full bathroom, comfortable seating and a small writing desk. A mini-fridge, microwave, and coffee maker is available for simple meal prep.Green Springs Inn is nestled on over 100 acres in the Cascade-Siskiyou National Monument. Our nature-immersive micro-resort is tucked away in one of the most biologically diverse areas in North America. We take land stewardship seriously, and we know you do too. Please respect the land and thank you in advance for following all of our rules. We have these rules to protect the land, ourselves, our guests, and our community.Please be advised that all guests will be asked to sign a rental agreement that governs the terms

Located in Ashland, New York, United States. Stacy's 2nd St Cottage. Steps to downtown. 1200 sq ft cottage located downtown in quiet residential area in historic Railroad District . 2 blocks to Shakespeare Festival and 92 acre Lithia park with walking, hiking ,playground and year round Ashland creek. One block to shopping, dining and Varsity movie theater. Walking distance to Southern Oregon University . Our cottage has 2 bedrooms and 1 bath with double sink. One bedroom has king bed, 2nd bedroom has two twin beds. Kitchen fully equipped. Washer/Dryer, wireless internet, 2TVs one with built in DVD, Apple TV with Netflix.Outside area is a beautiful large private courtyard with tables, chairs, propane fire-pit with comfortable seating , a propane barbecue and a private hot tub spa just for your use. Access to 2nd street through front courtyard gate entrance. Private off street parking with easy access to back entrance of cottage. Park your car and leave it, easy walking to downtown ,theaters and grocery stores. Electric ou

Located in Ashland, New York, United States. BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from OSF, theaters, Plaza and Downtown. VICTORIAN ROSE (2 BDRM-2 BATH-Sleeps 6)Let this beautiful cottage in a historic home fill you with a sense of comfort and luxury. This 875 square feet home has two bedrooms, each with a queen bed. A queen sleeper sofa in the living room can sleep another two people (or use the queen air mattress instead). One of the bedrooms has an attached bathroom with a walk-in shower. The second bathroom is newly renovated and has a combination tub-shower and the expansive kitchen is fully stocked to cook elaborate or simple meals. Enjoy your coffee/glass of wine in the separate dinning room, on the front porch overlooking the garden, or simply step out to the many neighborhood restaurants and cafes. A private back porch affords additional quiet reading or dining s

Located in Ashland, New York, United States. East Main Downtown Bungalow This is a beautiful new one bedroom bungalow with 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 new appliances, microwave and dishwasher. This bungalow is in a prime location, a 5 minute walk to the popular Shakespeare Festival, restaurants and shops.

Located in Ashland, New York, United States. Swank House on Main St in Ashland Summary:Dip into an Ashland vacation experience unlike any other. Stroll to your morning coffee or evening theater show from our newly renovated Main St home. Indoors, breathe easy with soaring vaulted ceilings and luxuries like the soaking tub and fully equipped kitchen.Outside, spend time with your feet up on the private outdoor patio. Our house is ideal for couples or families seeking extra space and privacy. A Swank House property. (#18-243)The Space:Expect beautiful luxuries like the soaking tub, sleek and clean finishes with everything you need: Coffee maker, spacious kitchen counter area, side yard for entertaining, front porch for wine drinking or reading, and two bedrooms with a King + Queen. 100% remodeled and designed by us. Bedroom 1: Beautiful views of the hills, four poster King bed with ample closet space, cozy sitting area to enjoy your morning coffee and private bathroom with tile surround shower.Bedroom 2: Queen size bed with close

Located in Ashland, New York, United States. 5 bedroom historic home with brand new furnishings, and is perfect for up to 14 guests. What this place offersBedroom and laundryWashing machineEntertainmentTVHeating and coolingAir conditioningInternet and officeWifiDedicated workspaceKitchen and diningKitchenSpace where guests can cook their own meals

Located in Ashland, New York, United States. The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District Located on the second floor, this petite yet whimsical guest room features exposed brickwork, a clawfoot tub for soaking, and one of the original cast iron beds from the hotel dating back to the 1920s. Its period inspired décor and floral details welcome you home as one of the best examples of “vintage coziness” our historic hotel has to offer. Every Peerless room is walking distance from all the restaurants, activities, and Oregon Shakespeare Festival performances Ashland has to offer!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 may result in additional per person fees if applicable ($20 per person per night) or up to/including reservation termination.- Partie

Located in Ashland, New York, United States. The Peerless Hotel | Anniversary Suite #3 | Twin Soaking Tubs | Historic District Welcome to our most luxurious and romantic suite. Featuring a full private bathroom with the famous “twin tubs” that are original to the Peerless Hotel. The vintage décor and hand painted gold accents invite you to take a step back in time in this true Victorian era inspired space. Unwind from the day’s adventures with complimentary champagne and a bubble bath or cozy up next to the fireplace. With a separate powder vanity in the bedroom, this suite is perfect for a romantic getaway for two!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 may result in additional per person fees if applicable ($20 per person per night) or up to/including reservation termin

Located in Ashland, New York, United States. Charming house two blocks from downtown Ashland The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comforts you will need. Cozy beds for sleeping late, a full kitchen with a complimentary coffee bar, a living room for socializing with family and friends, and all the privacy of having the entire property to yourselves. Restaurants, shopping, and theater begin two blocks away. This is the perfect house for your unforgettable Ashland experience.

Located in Ashland, New York, United States. Oberon -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 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. OBERONThis lovely 550 sq ft apartment will make you feel cozy and right at home with a kitchenette, cork floors, stainless steel appliances, a coffee maker, and full cooking and eating utensils.As you wake up in your soft organic bamboo cotton sheets covered in down pillows and blankets, you look