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Entire apartment·Private host

The Urban Gypsy Loft

Apartment in Ashland with kitchen

Photo gallery for The Urban Gypsy Loft

Fridge, microwave, oven, coffee/tea maker
Interior
Interior
Interior
2 bedrooms, desk, WiFi, bed sheets
Step into the heart of downtown Southern Oregon at The Urban Gypsy Loft, where art and culture meet adventure. This vibrant 2-bedroom loft is within walking distance to world-class theater, restaurants, wineries, and shopping. Unwind above the bustling Main Street with access to a breakfast spot directly below.

Reviews

9.8 out of 10
Exceptional

Entire apartment

2 bedrooms1 bathroom

Popular amenities

  • Parking available
  • Laundry
  • Kitchen
  • Air conditioning
The current price is €244
includes taxes & fees
5 Nov - 6 Nov

Add dates for prices

About this property

Entire place

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

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!

Property amenities

Internet

  • Available in the apartment: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV

Laundry

  • Laundry facilities

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

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)

Similar properties

Property grounds

The Maple Apartment at Tudor House Vacation Rentals

  • Kitchen
  • Air conditioning
  • Outdoor space
  • Parking available
9.6 out of 10, Exceptional, 153 reviews
The Maple Apartment at Tudor House Vacation Rentals

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

Rules

Do not use fireplace, not a working fireplace

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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

About the area

Historic Downtown District, a neighbourhood in Ashland, is home to this apartment. Weisinger Family Winery and Grizzly Peak Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore North Mountain Park and Cascade-Siskiyou National Monument. ScienceWorks Hands-On Museum and The RRRink are also worth visiting.
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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
  • ‪RedZone Sports Bar N' Grill - ‬2 min walk
  • ‪The Growler Guys - ‬2 min walk
  • ‪Blue Toba - ‬4 min walk
  • ‪Taqueria Picaro - ‬5 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 5 Oct 2025, prices found for a 1-night stay for 2 adults at The Urban Gypsy Loft on 5 Nov 2025 start from €244.41, 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.

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