See all properties
Entire home

Charming house two blocks from downtown Ashland

Choose dates to view prices

Photo gallery for Charming house two blocks from downtown Ashland

A single-story house with a covered porch, a small garden area with various plants, and a gravel driveway.
A modern kitchen with blue cabinets, a large window, and a sign on the wall.
living room and front door
A dining area with a round table, six chairs, and a wooden cabinet. There are two windows with white blinds, and artwork is displayed on the walls.
A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

Reviews

9.6 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Ashland, OR
  • Place, Lithia Park
    ‪11 min walk‬
  • Place, Oregon Shakespeare Festival
    ‪11 min walk‬
  • Place, Southern Oregon University
    ‪12 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪23 min drive‬

Room options

About the neighborhood

Ashland

Located in Historic Railroad District within a 5-minute walk of Ashland Library, this vacation home is within a 15-minute stroll of Oregon Cabaret Theatre. The vacation home includes a kitchen, a patio, and a refrigerator.
View more Vacation Homes in AshlandOpens in a new window

What's nearby

  • Ashland Library - 5 min walk - 0.3 miles
  • Oregon Cabaret Theatre - 8 min walk - 0.5 miles
  • Lithia Park - 11 min walk - 0.6 miles
  • Oregon Shakespeare Festival - 11 min walk - 0.6 miles
  • Southern Oregon University - 12 min walk - 0.7 miles

Getting around

  • Rogue Valley Intl. Airport (MFR) - 25 min drive

Restaurants

  • ‪Ruby's - ‬10 min walk
  • ‪RedZone Sports Bar N' Grill - ‬6 min walk
  • ‪Noble Coffee Roasting - ‬7 min walk
  • ‪Cocorico - ‬7 min walk
  • ‪The Growler Guys - ‬6 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.
The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. The bathroom offers hair dryers and bidets. Other standard amenities include a washing machine, a coffee maker, and a safe.

Similar properties

An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.
Stratford Inn
Siskiyou-Hargadine Historic District
  • Pool
  • Hot tub
  • Breakfast included
  • Pet friendly
9.4 out of 10, Exceptional, 1,797 reviews
$94 nightly
The price is $105
Nov 3 - Nov 4
Total with taxes and fees
Stratford Inn

Property amenities

Ski

  • Close to skiing

Internet

  • Available in the house: WiFi

Parking and transportation

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Bidet
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 50 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in public areas
  • Gravel flooring in public areas
  • Hardwood flooring in public areas
  • Tile flooring in public areas
  • Well-lit path to entrance
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Safe

Location highlights

  • In the city center

Things to do

  • Cycling nearby
  • Rafting nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit

General

  • Electric car charging station
  • Garden
  • Recycling

Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Dogs only
  • 1 total (50 lbs is the maximum weight per pet)
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Frequently asked questions

What can I see near this vacation home?

This vacation home is situated in Historic Railroad District, just steps from Ashland Library, and within a 10-minute walk of Lithia Park and Oregon Shakespeare Festival. You'll also find Oregon Cabaret Theatre and Allen Elizabethan Theatre less than a mile away.

How much does it cost to stay at Charming house two blocks from downtown Ashland?

As of Nov 1, 2026, prices found for a 1-night stay for 2 adults at Charming house two blocks from downtown Ashland on Nov 2, 2026 start from $381, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is parking available on site at Charming house two blocks from downtown Ashland?

Yes, there is an electric car charging station available.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What will couples enjoy most about a stay at Charming house two blocks from downtown Ashland?

Couples staying at this vacation home will appreciate amenities like a kitchen and a smart TV as well as a garden.

Are there hot tubs at Charming house two blocks from downtown Ashland?

No, there isn't a spa tub at this vacation home.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this vacation home.

Are there connecting rooms at Charming house two blocks from downtown Ashland?

No, there aren't connecting guestrooms at this vacation home.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Rogue Valley Intl. Airport (MFR), which is 16.6 mi away (25 minutes by car).

Are there rooms with balconies that I can book at Charming house two blocks from downtown Ashland?

Yes, every house at Charming house two blocks from downtown Ashland comes with a patio and some offer mountain views.

Charming house two blocks from downtown Ashland Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 9 out of 12 reviews
Rating 8 - Good. 3 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.8/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is our favorite spot to stay in Ashland! The location is perfect for walking downtown to the shops and theaters, shopping at the local co-op, or just enjoying a sunny breakfast on the deck.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Serendipity house is a charming old house with excellent signage. Perfect for a visit to Ashland to take in an Oregon Shakespeare Festival play!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming as can be and at the perfect location for all that Ashland has to offer. The neighborhood is quiet and friendly with lots to offer.
Stayed 5 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice stay

Well located, nice house!
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Spot for our Ashland Visit!

This cottage was our home away from home. An easy walk to downtown and OSF and a perfect spot to relax after a day of wine tasting. Comfortable, well-equipped, and pet-friendly.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
One of the best places I've ever stayed at! Great location, amazing house - everything is such great condition and clean. Such a wonderful experience. You can tell the host really puts a lot of thoughts into this place. Everything's perfect there. We love it!
Stayed 1 night in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A beautiful Redwood in a field

I can't say enough about how wonderful this house was..... Location was perfect, off street parking was great, the house was perfect for 2-4 people, clean, well stocked with essentials, laundry on site....just an amazing place to stay. We will definitely book this again when visiting family.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for what we needed. We come to Ashland to attend the Shakespeare Festival and being in this location was perfect because it was only about a 15 minute walk. The property itself is beautiful and clean and had everything that we could’ve wanted. I believe that parts of the welcome manual should be sent to whoever reserves the property before hand because we were not told where to park when we got there, but we were able to figure it out. I would definitely reserve this location again if/when I come back. Thank you for a wonderful experience.
Stayed 5 nights in Sep 2025
Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy
I have stayed at this property twice now through two different bookings and both times i have had to call, text, message the property manager for the check-in door code. I have even had to call both platforms where this rental is listed because i have not heard back in a timely manner. That is literally the only disappointing thing about this property. We love this little house so much and it is a joy to stay here. So clean and well kept. I just wish getting the check in information was easier.
Stayed 2 nights in Jun 2025
Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy
Disliked: Communication
Property was exactly as promoted. Comfortable, clean, with great kitchen amenities. Back porch was suitable for backyard birding, spotted 15 species! Walk from theaters was flat, well lit, and felt safe. Communications with host/manager were problematic. One day before check in and no information about access. Texted and called to get information then waited. Host did send door code before arrival, however, it didn’t work. The first morning while we were having coffee (9am) on porch we were startled when two men came into back yard. They identified as the gardeners but there was no notification from host to expect them. Last morning a woman tried to get into the house. It was the cleaner, arriving before checkout without knocking or checking to see if anyone was inside.Sadly, our last morning was lost doing housekeeping before the cleaner arrived at 10:45. I question the price point of the cleaning fee when occupant is requested to launder towels, clean frig, empty trash and tote garbage to recycle bins on edge of property.
Stayed 4 nights in Sep 2025
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Nov 2024