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The Urban Gypsy Loft

Apartment in Ashland with kitchen

Photo gallery for The Urban Gypsy Loft

Interior
Interior
Interior
Interior
Room

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Parking available
  • Laundry
  • Kitchen
  • Air conditioning

Explore the area

View map
Ashland, OR
  • Place, Oregon Shakespeare Festival
    ‪6 min walk‬
  • Place, Lithia Park
    ‪6 min walk‬
  • Place, Southern Oregon University
    ‪14 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪25 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

1 bathroom

Bathroom 1

Spaces

Kitchen
Separate dining area
Dining area

About this property

The Urban Gypsy Loft


Within walking distance, enjoy world-class Shakespeare theater, restaurants, wineries, shopping, unique coffee shops, and endless outdoor adventure with a stunning scenic backdrop! You'll be above all the fun in a hip, colorful 2 bedroom loft. Art, culture, and downtown vibes - The Urban Gypsy Loft in Southern Oregon checks all the boxes for the best weekend getaway, girl's trip or stay-cation. If outdoor adventure is your jam, you chose the right town!

This apartment is located upstairs in a 3-unit historic building on Main Street. The spacious apartment features the following;

Guest access is given within a few hours of check-in. You'll be given a unique code that allows you access into the building, and a separate code to get into the loft. Safety is a high priority for our guests :)

Other things to note; there is a breakfast spot directly below our loft, a yummy Italian restaurant, and a sexy wine bar open until 11 pm, so you can literally walk out the door and be at any of these places within seconds!

Add dates for prices

Amenities

Kitchen
Air conditioning
Laundry
Parking available

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Do not use fireplace, not a working fireplace

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property

About the area

Ashland

Historic Downtown District, a neighbourhood in Ashland, is home to this apartment. The area's natural beauty can be seen at North Mountain Park and Cascade-Siskiyou National Monument, while Oregon Cabaret Theatre and Oregon Shakespeare Festival are cultural highlights. Looking to enjoy an event or a game while in town? See what's happening at Lithia & Driveway Fields or The RRRink.
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Map
Ashland, OR

What's nearby

  • Oregon Cabaret Theatre - 3 min walk - 0.3 km
  • Allen Elizabethan Theatre - 6 min walk - 0.6 km
  • Oregon Shakespeare Festival - 6 min walk - 0.6 km
  • Lithia Park - 6 min walk - 0.6 km
  • Southern Oregon University - 14 min walk - 1.2 km

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 26 min drive

Restaurants

  • ‪Ruby's - ‬6 min walk
  • ‪The Growler Guys - ‬2 min walk
  • ‪Taqueria Picaro - ‬5 min walk
  • ‪RedZone Sports Bar N' Grill - ‬2 min walk
  • ‪Blue Toba - ‬4 min walk

Frequently asked questions

Is The Urban Gypsy Loft pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Urban Gypsy Loft?

As of 2 Nov 2025, prices found for a 1-night stay for 2 adults at The Urban Gypsy Loft on 3 Nov 2025 start from AU$350.59, 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.

What time is check-in at The Urban Gypsy Loft?

Check-in begins at 4:00 PM.

What time is check-out at The Urban Gypsy Loft?

Checkout is at 11:00 AM.

Where is The Urban Gypsy Loft located?

Located in Historic Downtown District, this apartment building is within a 5-minute walk of Ashland Library, Oregon Cabaret Theatre and Allen Elizabethan Theatre. Angus Bowmer Theatre and Thomas Theatre are also within 5 minutes.

Reviews

9.8

Exceptional

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 6 out of 7 reviews
Rating 8 - Good. 1 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

Reviews

10/10 Excellent

Laurie V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy space located close to theater.
Stayed 3 nights in Sep 2025

10/10 Excellent

Rolanda S.

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

Early June stay

We had difficulty checking in but our host was easily accessible for us to gain entry. We appreciated the short walk to the theaters and not hassling with parking. Great restaurants and the downstairs bakery are a great benefit
Stayed 2 nights in Jun 2025

10/10 Excellent

Jodi A.

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

Charming historic flat on charming Main Street

This 2 bedroom flat is very spacious, with plenty of room to relax and enjoy your company. The front room has a dining area, and spacious sitting area overlooking Main Street. There is a tv room, 2 bedrooms and a kitchen. It’s is a very cozy, comfortable and homey flat. Walking distance to everywhere is downtown Ashland. The street noise is a factor. The host has supplied everything possible to make it tolerable. We were not bothered by it, but it is like staying centrally in a city environment. You get all the perks of everything at your doorstep, with the typical noise that comes with it.
Stayed 3 nights in Nov 2024

10/10 Excellent

Matt S.

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

Shakespeare in Ashland

Property is well placed for walking to the theater's, restaurants and core town downtown shops.
Stayed 3 nights in Jul 2025

8/10 Good

Maureen S.

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

Can't beat the location

Not the best for seniors- 26 steep steps and no grab bars or mat for the shower. That being said it was comfortable and beautiful.
Stayed 3 nights in Jun 2025

10/10 Excellent

Christina M.

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

Urban Gypsy Loft 5 Stars

We had the most amazing stay in Ashland at the Urban Gypsy Loft. Alisha was a wonderful host and her loft is absolutely adorable. The beds were big and SO comfortable. Perfect walking distance through the Historic District. Can't wait to visit again some day.
Stayed 2 nights in Mar 2025

10/10 Excellent

Corey L.

Stayed 1 night in Jun 2025

About the host

Hosted by Alisha

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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