Vacation Home Rentals By Owner In Ashland, OR

$244.74

Peaceful 1-bedroom bungalow with AC in charming Ashland

Ashland, Oregon, United States

Consider this bungalow your home away from home while you visit Ashland. Easy walking distance to everything Ashland has to offer. Located 1 block north of the downtown plaza; many restaurants, boutiques/shops, Lithia Park/Japanese Garden and theaters (Oregon Shakespeare Festival and Oregon Cabaret Theatre). This quaint retreat features full size and functional kitchen with eating bar/barstools, A garden view bedroom with a queen bed, perfect for a restful night. Large bedroom closet with built in drawers. The bathroom offers a step-in tiled shower and a convenient bidet for added comfort. Heating and air conditioning keep the space comfortable year-round. Enjoy your private patio and garden to sit and enjoy your morning coffee. Whether you’re relaxing indoors or exploring nearby, this beautiful bungalow provides a peaceful spot to unwind. A great place to call homebase while you're away.

1

Bed

1

Bath

2

Sleeps

$105.67

/ Nightly

Private Vacation Home

Comfort and calm in Ashland

Ashland, Oregon, United States

Relax and have fun with the whole family in this stylish home. Fully outfitted kitchen, gas fireplace, private back yard and family friendly space. brbrOn the first floor there is a comfortable family room with fireplace, television, a full kitchen with top-of-the-line appliances including dishwasher, gas stove, oven, fridge and freezer, a bar that seats 4 people and a dining area and a half-bath. On the second floor, there are 3 bedrooms, 2 full bathrooms, a washer and dryer.brbrbrbrMy husband and I are retired. We love to travel and enjoy theater, the outdoors, and our family and friends.

3

Bed

2

Bath

6

Sleeps

$380.96

/ Nightly

Private Vacation Home

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Ashland, Oregon, United States

Step into a piece of Ashland history at the Ohana House, a charming 1905 3-bedroom, 2-bath home just a 2 minute walk from downtown. Blending modern comfort with vintage style and Hawaiian charm, this spacious getaway features a private outdoor hot tub and outdoor shower, an inviting Tiki bar, and plenty of room to relax with family or friends. Additional amenities include fast wifi, office space with printer and copy machine, and a stereo system with record player. brbrEnjoy movie nights under the stars with the outdoor projector, unwind on the deck, cook in the fully stocked kitchen, or stroll through Lithia Park just blocks away. Large fenced yard with play structure, barbecue grill, laundry, and off-street parking included. Pet-friendly for your furry companions! brbrThis 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. three large screen TV’s, original wood floors, pantry, and all kitchen appliances necessary to cook or bake. brbrHave a family game night, listen to your favorite tunes on a vintage Marantz stereo system while making drinks at the bar, or grilling on the barbecue out on the deck. The options for how you want to enjoy your stay are endless!brbrMahalo for considering my home, for your stay in Ashland ~ Michael brbr****Please feel free to call or text 541-601-7493 for additional information****

Bed

Bath

Sleeps

$540.78

/ Nightly

Private Vacation Home

Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland

Ashland, Oregon, United States

This luxury vacation rental is uniquely designed for elegance and comfort that will make you feel right at home. The newly renovated craftsman home can be rented as a 3 bedroom, 2 bathroom home, or split into two separate one bedroom units - making it perfect for couples, larger families and groups or singles. Relax 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. brbrTitania and Oberon combined br( VRBO555935 and VRBO 560782 )brThis beautiful 1,400 sq. ft. 3 bedroom, 2 bathroom unit offers a full state of the art kitchen with stainless steel appliances, granite counter tops, cork floors, an espresso machine, coffee maker juicer, full eating and cooking utensils, 6 burner stove top and oven, dishwasher and dining area with a table that folds out to seat 6. brThe living room will make you feel right at home with books, games, 40 inch flat screen t.v, bose sound system, leather couches and views of the mountains and downtown Ashland.brThe master bedroom suite has a full walk in closet, 42 inch flat screen T.V., a queen-size bed with organic sheets, goose down pillows and comforter and an ihome radio/music player. The bathroom has a rainwater shower/bathtub and granite countertops. The second bathroom has granite countertops and a rainwater shower. We offer shampoo, conditioner, body wash, local lavender oatmeal soap and local organic jojoba and Shea butter lotion.brThe second bedroom looks out over the zen gardens and is filled with the sound of the crystal water fountain. The bedroom has organic cotton sheets, goose down pillows and blankets, a walk-in closet, alarm clock and 42 inch smart T.V. brThe third bedroom is incredibly versatile as it can be a twin, queen, or a 2 twin bedroom. Smaller parties use it as a game/tv room. The room looks out over the zen gardens and offers books, games, a Bose radio, 32 inch flat screen tv and a table with chairs.brThe also has a covered porch with a couch to watch the world go by, a deck with a seating area facing the mountains and a large gated yard with beautiful lush gardens and outdoor seating for 6.brbr* We only use non-toxic cleaning products and detergents. br*We can also replace down bedding for non-down bedding brbrPA# 13 - 1476

Bed

Bath

Sleeps

$209.9

/ Nightly

Private Vacation Home

Chateau Herb ~ Juliet Carriage House Studio

Ashland, Oregon, United States

Welcome to the Carriage House Juliet at Château Herbe — a charming private apartment set within a luxurious contemporary château estate. Nestled inside a gated castle community, this elegant retreat offers comfort, privacy, and stunning surroundings designed for a relaxing getaway.brbrSurrounded by classical gardens, orchards, vineyards, tranquil water features, and sweeping mountain views, the property creates a peaceful European-inspired escape just minutes from I-5 and downtown Ashland.brbrGuest AccessbrbrGuests are invited to enjoy the château’s shared sunroom, library, coffee bar, and patio spaces. Stroll through the vineyard, gardens, orchards, pond, pergola, and classical fountain while taking in the beauty of the estate grounds.brHot tub and sauna are available year-round for your enjoyment.

Bed

Bath

Sleeps

$247.65

/ Nightly

Private Vacation Home

European Style Straw Bale Retreat

Ashland, Oregon, United States

Absorb the beauty of this European-style straw bale home located on 14 wooded acres in Ashland. Minutes from downtown, this eco-friendly retreat guarantees a meditative stay while ensuring you're never far from dining or shopping. An open floor plan, earthen floors, vaulted ceilings & soapstone fireplace make the living area the ideal space to relax. After a day spent exploring or skiing, enjoy the hot tub right outside. Property managers live dowhill, to ensure your stay is always comfortable!brbrThe spacebrThis is a pet free stay and there will be a minimum charge of $150 if any pet hair or damage is found.

Bed

Bath

Sleeps

$224.08

/ Nightly

Private Vacation Home

Ashland Urban Cabin - Centrally located & walking distance to SOU and Downtown

Ashland, Oregon, United States

Centrally located in the heart of Ashland, this cozy, thoughtfully updated retreat features 2 beautifully styled bedrooms with queen beds and soft, high-quality bedding, a bright and spacious living room with a wood-burning fireplace, a full bathroom, and a well-equipped, stylish kitchen. Walking distance to Southern Oregon University and Ashland’s vibrant cultural scene—ideal for both relaxation and adventure!brbrBeyond its charm and creative touches, the home has been consciously updated to support a naturally clean and refreshing environment. Filtered drinking water is provided through a dedicated kitchen tap. Eco-friendly, non-toxic materials have been used throughout, and the space is free from artificial fragrances. Thoughtfully maintained with natural cleaning and personal care products, the home offers a mindful retreat that is as healthy as it is inviting.brbrEnjoy two separate outdoor patios, including a fenced area with a fire pit and string lights, perfect for sipping morning coffee or unwinding beneath the stars. Off-street parking is also provided for your convenience.brbrGuests have access to the entire first floor, including the cozy living room with a woodstove, a well-appointed kitchen, two comfortable bedrooms, a full bathroom with a bathtub, a convenient laundry area, and all outside patios and courtyards.brbrThe owner maintains the upstairs as a private suite that is not accessible to guests. However, the home is not a shared space, and the owner will not be on-site during guest stays, ensuring complete privacy throughout your visit. There is a locked cleaning closet and cupboards that are also reserved for owner’s personal belongings and cleaning supplies.brbrWhile you relax, you may encounter a couple of the property’s friendly feline residents. These outdoor cats occasionally wander by to say hello, adding a touch of charm to your stay.brbrI’m available to assist with any questions or issues that may arise, but I respect guests’ privacy and won’t interfere or interact unless needed.

Bed

Bath

Sleeps

$340.08

/ Nightly

Private Vacation Home

ABBOTT'S COTTAGES, Avocet cottage- 3 bdrm/2bath, walking distance to downtown

Ashland, Oregon, United States

A beautiful 3 bedroom/2 bath house perfect for families and groups. Quiet, clean and comfortable. Just a 0.7 mile walk to the plaza. brbrThere are other cottages (another 3-bedroom, two 1-bedrooms and a studio) on the property if you are looking for more than one place. Just let us know!brbrNote: Abbott's Cottages is a small family business made up of 9 cottages, all within walking distance to downtown. We have been renting our cottages to tourists in Ashland for 25 years and we usually get 5 star reviews on our other booking platforms. We took a break from renting through VRBO but now we are back- just to explain when you see no reviews! We also have cottages at other locations and soon they will be listed here- in the meantime you can look up Abbott's Cottages to view them all :)

3

Bed

2

Bath

10

Sleeps

$181.69

/ Nightly

Private Vacation Home

The Red Dragon House

Ashland, Oregon, United States

The Red Dragon House is a great location for those who wish to discover Ashland, along with the southern Rogue Valley, but still get that rural feeling while remaining only minutes from town. The single-story house is spacious at nearly 1,000 square feet, and features mountain views of the southern Rogue Valley. The house features a large open living room/kichen area, with lots of counter space, two well-appointed bedrooms and a bathroom shower, suitable for those with mild handicaps, and has three decks from which to choose, all on a property that is 5.2 acres, in a rural neighborhood, that's quiet. All this only five minutes from the nearest restaurants and markets, and ten minutes from Downtown Ashland, and the Mt. Ashland Ski Area is only 19 miles away!brbrWhile the neighborhood is quiet, it should be mentioned that the property is adjacent to I-5, which makes getting to us easy, but does provide some road noise. So, if it's total quiet you require, this may not be the best fit for you, though the there is no road noise inside the house.

Bed

Bath

Sleeps

$713.99

/ Nightly

Private Vacation Home

Hot tub | Sauna |Firepit |Sleeps 6!

Ashland, Oregon, United States

This modern home features a brand-new hot tub, sauna, outdoor fire pit, grill, and an outdoor shower. Enjoy a gourmet kitchen, a bar with wine fridge, sweeping valley views, & reclaimed wood accents throughout. brbrWith 2 bedrooms and a pull-out couch in the TV room, this spacious home has room for 6. The primary bedroom offers a king bed with valley views, & the second bedroom features a queen bed with full private bath. brbrRelax by the fire or stargaze from the hot tub—your luxury retreat awaits!brbr*DISCOUNTED OSF TICKETS*brbrWanderLodges is proud to be an OSF Lodging Partner for the Oregon Shakespeare Festival’s 90th season! As part of this special partnership, all guests with a confirmed reservation at any of our properties will receive an exclusive 20% discount code for OSF tickets in B and C sections—valid for the entire season!brPlease do not wear shoes inside the house. The floors are a soft reclaimed wood and susceptible to damage. We greatly appreciate your understanding and respect of the space.brbrUnfortunately the indoor fireplace is not available for guest use per our insurance requirements. Additionally, the wood burning fire pit off the side deck is not for guest use due to the home's location in a high risk fire area. You are welcome to use the gas fire pit on the patio. Be sure to use the key next to the patio door to turn the gas on and off after use.

Bed

Bath

Sleeps

$215.72

/ Nightly

Private Vacation Home

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Ashland, Oregon, United States

This property is a secluded mountain getaway in the Southern Cascades near Ashland Oregon. The cabin is stocked with dishes, a mini kitchen w/toaster oven, microwave, refrigerator, and coffeemaker. Cook outside on a gas grill. Relax around a fire pit or soak in an outdoor tub. The cabin is on five forested acres, and next to a seasonal creek. Nearby lakes offer boating, and kayaking. Hiking trails are nearby. Crater Lake National Park is 50 miles from the cabin. Sleeps up to 4.

Bed

Bath

Sleeps

$625.96

/ Nightly

Private Vacation Home

House + 2 Studios- 3 blocks from the Plaza!

Ashland, Oregon, United States

Helman House and Cottages ~ Old Ashland Charm, Short Walk to the Plazabrbr★HOME OVERVIEW★brOne and a half blocks away from Main St. on a quiet, tree-lined street you’ll find old-Ashland charm in the Helman House and Cottages. Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival—boutique shops, award winning wineries, and restaurants Ashland is famous for, The Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer.brbrYour reservation will include the Helman House and two cottages behind the house (sleeps 16). brbr★SLEEPING ACCOMMODATIONS★brbrWe can sleep 16 total!brbrFront House Bedroom 1: King Bed, ensuite bathroom with walk in showerbrFront House Bedroom 2: 2 Queen beds. This bedroom is up a narrow staircase and has no door.brFront House Living Room: Queen fold out couchbrThere is another full bathroom with bathtub off of the kitchenbrbrStudio A: King Bed and Queen fold out couch and ensuite bathroom with bathtub brStudio B: King Bed and Queen fold out couch and ensuite bathroom brbr★LIVING AREA★brRelax on our sofas and stream your favorite shows on our Smart TVs (Roku). Enjoy access to Netflix, Hulu, Prime Video, and Apple TV by simply entering your password. There are 3 TVs total. One in each unit. br‎br★KITCHEN★brThe kitchen in the front house is perfect for simple meal prep when you need a night in. You'll find all your basics to get breakfast, lunch or dinner on the table. Enjoy a 2-in-1 coffee maker with both Keurig and drip options. Each studio is equipped with its own efficient kitchenette so you can have a cup of coffee before joining the rest of the group!br‎br★BATHROOMS★brThere are 4 full bathrooms total including 2 bathtubs (Front house and Studio A). Towels, shampoo, conditioner and body wash are provided.brbr★LAUNDRY ROOMS (yes, plural!)★brThere is a full sized washer and dryer in the bathroom in the front house and another one in studio A!brbr★PARKING★brThere are 2 off street parking spaces reserved for you behind the house as well as ample street parking. brbr★FRONTYARD★brEnjoy a cup of coffee on our Adirondack chairs while people watching or a quick bite on our table for 4 on the front porch.brbr★RESTAURANTS & BARS★brThe best of the best on the Ashland Plaza is a 6 minute walk away!brbr★HEATING & AC★brThe main house has a central heat and AC. The studios are equipped with window units that have both heat and AC. brbrPerfect for a multi-party or family gathering, the Helman House and Cottages provide comfort and convenience for all.brbrPlease note that the wall shared by both studios is relatively thin as far as soundproofing goes. brPlease Note: The water heater is shared between Studio A and Studio B. While it generally provides sufficient hot water for both units, there may be occasional delays in hot water recovery if multiple showers are taken back-to-back. We recommend spacing out showers when possible for the most comfortable experience.brbrFor safety, there is a ring doorbell at the front door. It is active 24/7. Video and sound recording is motion activated. The home is also equipped with a decibel monitoring sensor located inside and outside of the home. It is 100% privacy compliant and is required on this property. Tampering with or disabling the ring doorbell and noise monitoring sensor will immediately cancel the reservation.brbrThere is a pet fee of $150 (up to 2 pets)brPet Policy ReminderbrWe love welcoming well-behaved pets to our property! To help ensure a safe and enjoyable experience for everyone, we kindly ask that all pets be kept on a leash when outdoors and not left unattended in shared areas.brThank you for your understanding and cooperation!brbrbrIMPORTANT REMINDERS:br- You will be asked to sign a rental agreement.br- The minimum age to rent is 21br- No smokingbr- Garden maintenance occurs on Fridays. Our team ensures the garden remains in excellent condition for your enjoyment.brbrCancellation Policy: 50% refund up until 60 days prior to arrival. No refund if cancelled within 60 days.brbrEarly Check-In / Late Check-Out Options:br - We may be able to accommodate an early check-in starting at 1:30 PM or a late check-out until 1:30 PM for an additional fee of $150.00, subject to availability and scheduling.br - To help us coordinate with our cleaning and operations teams, requests must be made at least 1 day in advance and are not guaranteed until confirmed by management.br - For guests needing significantly earlier arrivals or later departures, we recommend booking the previous or following night to ensure uninterrupted access to the property.br - Unapproved late checkouts will incur an additional charge of $300.

4

Bed

4

Bath

16

Sleeps

$452.9

/ Nightly

Private Vacation Home

Downtown Ashland House - Walk to Plaza and OSF!

Ashland, Oregon, United States

Helman House ~ Old Ashland Charm, Short Walk to the Plazabrbr★HOME OVERVIEW★brOne and a half blocks away from Main St. on a quiet, tree-lined street you’ll find old-Ashland charm in the Helman House. Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival—boutique shops, award winning wineries, and restaurants Ashland is famous for, The Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer.brbr★SLEEPING ACCOMMODATIONS★brbrWe can sleep 6 total!brbrFront House Bedroom 1: King Bed, ensuite bathroom with walk in showerbrFront House Bedroom 2: 2 Queen beds. This bedroom is up a narrow staircase and has no door.brFront House Living Room: Queen fold out couchbrThere is another full bathroom with bathtub off of the kitchenbrbr★LIVING AREA★brRelax on our sofa and stream your favorite shows on our Smart TV (Roku). Enjoy access to Netflix, Hulu, Prime Video, and Apple TV by simply entering your password. br‎br★KITCHEN★brThe kitchen is perfect for simple meal prep when you need a night in. You'll find all your basics to get breakfast, lunch or dinner on the table. Enjoy a 2-in-1 coffee maker with both Keurig and drip options.br‎br★BATHROOMS★brThere are 2 full bathrooms total; one newly renovated with a bathtub/ shower combo and the other with a full sized shower. Towels, shampoo, conditioner and body wash are provided.brbr★LAUNDRY ROOM★brThere is a full sized washer and dryer in the bathroom off the kitchenbrbr★PARKING★brThere is 1 off street parking space reserved for you behind the house as well as ample street parking. brbr★FRONTYARD★brEnjoy a cup of coffee on our Adirondack chairs while people watching or a quick bite on our table for 4 on the front porch.brbr★RESTAURANTS & BARS★brThe best of the best on the Ashland Plaza is a 6 minute walk away!brbr★HEATING & AC★brThe house has a central heat and AC. brbrThere are 2 cottages in the back of the property available for rent separately, perfect for a multi-party getaway.brbrFor safety, there is a ring doorbell at the front door. It is active 24/7. Video and sound recording is motion activated. The home is also equipped with a decibel monitoring sensor located inside and outside of the home. It is 100% privacy compliant and is required on this property. Tampering with or disabling the ring doorbell and noise monitoring sensor will immediately cancel the reservation.brbrThere is a pet fee of $150 (up to 2 pets)brbrIMPORTANT REMINDERS:br- You will be asked to sign a rental agreement.br- The minimum age to rent is 21br- No smokingbr- Garden maintenance occurs on Fridays. Our team ensures the garden remains in excellent condition for your enjoyment.brbrPet Policy ReminderbrWe love welcoming well-behaved pets to our property! To help ensure a safe and enjoyable experience for everyone, we kindly ask that all pets be kept on a leash when outdoors and not left unattended in shared areas.brThank you for your understanding and cooperation!brbrbrCancellation Policy: 50% refund up until 60 days prior to arrival. No refund if cancelled within 60 days.brbrEarly Check-In / Late Check-Out Options:br- We may be able to accommodate an early check-in starting at 1:30 PM or a late check-out until 1:30 PM for an additional fee of $120.00, subject to availability and scheduling.br- To help us coordinate with our cleaning and operations teams, requests must be made at least 1 day in advance and are not guaranteed until confirmed by management.br- For guests needing significantly earlier arrivals or later departures, we recommend booking the previous or following night to ensure uninterrupted access to the property.br- Unapproved late checkouts will incur an additional charge of $300.

Bed

Bath

Sleeps

$527.15

/ Nightly

Private Vacation Home

Swank House in Downtown Ashland

Ashland, Oregon, United States

Summary:brbrDip 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.brbrOutside, 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)brbrbrbrThe Space:brbrExpect 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. brbrbrbrBedroom 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.brbrbrbrBedroom 2: Queen size bed with closet space and dresser to store your things. Bathroom features soaking tub, gold hardware, and tile surround shower with rain head.brbrbrbrGuest Access:brbrPark in our carport and walk everywhere!brbrbrbrThe Neighborhood:brbrCoffee shops abound, shopping around the corner and 1/2 block to a grocery store. Everything you need is within walking distance to our house on Main St.brbrbrbrGetting Around:brbrWe suggest walking as you are close to everything!brbrbrbrOther Things to Note:brbrThis house also has a semi-attached additional Airbnb unit. We have done our best to sound proof the one shared wall but you may hear faint sounds of life happening on the other side. This unit is located slightly below grade of the Main St House. There are separate entrances and separate patio areas. You share carport parking and the outdoor grilling area.

Bed

Bath

Sleeps

$515.64

/ Nightly

Private Vacation Home

2BR Ashland Retreat: Steps to Shakespeare

Ashland, Oregon, United States

Summary:brbr**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.brbrbrbrThe Space:brbrThis 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. Please see our other listings Matriarch-Suite 1 and Martiarch Suite 2 if you are interested in hosting a larger gathering.brbrbrbrThe Neighborhood:brbrThe Matriarch is located in the historical Railroad district of downtown Ashland.brbr--6 minute WALK to the doors of Oregon Shakespeare Festival brbr-- 5 minute WALK to over 20 restaurantsbrbr-- 1/2 block to the local food Co-opbrbr-- Local shopping awaits.brbrbrbrGetting Around:brbrWe recommend parking and walking everywhere to take full advantage of your time in Ashland. Parking downtown is limited therefore it's best to just walk!brbrbrbrOther Things to Note:brbrThe Matriarch Hotel also hosts several separate private guest suites on location. You may likely see these guests outside as they visit Ashland.brbrAshland permit: (#18-247)brbrbrbrInteraction with Guests:brbrWe value guests' autonomy but our staff is always available by text, phone or minutes away to serve you.

Bed

Bath

Sleeps

$407.02

/ Nightly

Private Vacation Home

Callahan's House

Ashland, Oregon, United States

Just a quick walk across the street from your private house to the main lodge, all while still being able to enjoy all the features and amenities the lodge has to offer. brbrThis Callahan House is perfect for large families or friends to gather or even use as a bridal suite.

4

Bed

2

Bath

8

Sleeps

Select Dates for Price

Private Vacation Home

Ashland Townhouse, furnished

Ashland, Oregon, United States

3 bedroom, 2 and 1/2 bath furnished townhouse located 1/2 mile from grocery shopping and the YMCA, 1 mile from Southern Oregon University, and 2 miles from downtown and the Oregon Shakespeare Festival. Quite neighborhood within the East Village HOA. Attached one car garage. Backyard sitting area with grape arbor and pergola. Full kitchen, breakfast bar, and dining room with powder room adjacent. Gas stove top, electric oven, microwave, generous counter tops and cabinets. Air conditioning, forced air gas heating. Walk in closet with each bedroom. Two bathrooms upstairs: One with tub shower, the other with large shower.

Bed

Bath

Sleeps

$375.39

/ Nightly

Private Vacation Home

New Downtown 3 Bedroom Upstairs Flat with views

Ashland, Oregon, United States

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 and well-known stores, antiques, parks, galleries, fabulous restaurants whether for happy hour or fine dining, bakeries, local micro brews and pubs, coffee shops... just about everything for an enjoyable visit to Ashland . The house is just blocks away from a convenient health conscious Co-op grocery store for everyday necessities and stocked with local fresh produce. Close to public transit makes this a great place to stay whether for work or fun!

3

Bed

2

Bath

7

Sleeps

$576.74

/ Nightly

Private Vacation Home

Whimsy on B | 2BR Steps to Downtown

Ashland, Oregon, United States

Welcome to Whimsy on B, a storybook hideaway just steps from the Ashland Food Co‑op & an easy stroll to downtown shops, theaters, & cafés. brbrInside, find two inviting bedrooms (a bright king with TV & a spacious queen) plus a cozy living room with a TV & a well- equipped kitchen.brbrOutside, sip coffee beneath blooming wisteria, sway on the porch swing, & watch Ashland drift by.brbrPlease note, this is one unit in a quiet triplex. You may see other guests in the shared parking area or back courtyardbrPOLICY REMINDERS:br- Cancelations are dependent on the channel and rate you booked. For direct and standard rates: Cancellations made 5+ days before arrival, a full refund minus a $39 cancellation fee will be issued (non-refundable rates excluded). After that, only the cleaning fee will be refunded.br- Occupancy Limits: Guests agree to not exceed maximum occupancy stated in the listing. $15 per person, per night is charged after the first 4 guests in a reservation. Failure to notify WanderLodges of accurate occupancy may result in additional per person fees if applicable or up to/including reservation termination.br- Parties/Large Gatherings: All parties or occupancy issue creating gatherings are strictly prohibited at all WanderLodges properties, and guests agree to comply with all city, company, and fire code noise and use requirements.br- Pets/Service Animals: Whimsy on B is not pet friendly at this time. As always, we are happy to accommodate registered service animals of our guests.br- Smoke Free: As a reminder, all WanderLodges properties are smoke and vape free. Smoking indoors, within 10 feet of an entry, or anywhere on the property will incur an additional $250 fee.br- Quite Hours: Considered between 10PM and 8AM. Please keep noise to a minimum in consideration of neighbors. Noncompliance of this will incur a $100 fee per incident, and/or a request to vacate.br- Damages: All damages must be reported to WanderLodges as soon as possible. By booking, guests agree to financial responsibility for all damages due to gross negligence and up to an additional $500 in cleaning fees for negligent use.br***** By booking, guests are agreeing that they are of 18 years of age or older, legally able to agree to these terms, and any minors part of the itinerary will always be accompanied by a parent or guardian. *****

2

Bed

1

Bath

4

Sleeps

$290.56

/ Nightly

Private Vacation Home

Whimsy on B | The Studio

Ashland, Oregon, United States

Welcome to this bright, spacious studio for two just steps from downtown Ashland & OSF. Sink into a comfy king bed with TV, enjoy meals at the bistro table, & cook easy favorites in the well‑equipped kitchenette (toaster oven + hot plate; no full oven). You`ll also have a full bathroom with shower. brStep outside to a quiet courtyard, perfect for a peaceful pause between Ashland adventures.brbrPlease note this is one unit in a quiet triplex, so you may see a neighbor in the backyard or parking area

1

Bed

1

Bath

2

Sleeps

Vacation Home Rentals By Owner In Ashland, OR

$244.74

$105.67

$380.96

$540.78

$209.9

$247.65

$224.08

$340.08

$181.69

$713.99

$215.72

$625.96

$452.9

$527.15

$515.64

$407.02

$375.39

$576.74

$290.56

Rent a place that suits your needs

Most popular vacation rentals in Ashland

$825.88

$845.40

$945.59

$994.76

$1205.56

$1315.89

$327.17

$305.66

$306.53

$306.87

Most Popular Cities in Oregon