Entire apartment

The Urban Gypsy Loft

Fridge, microwave, oven, coffee/tea maker

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.

Exceptional

Entire apartment

2 bedrooms1 bathroom

Popular amenities

Parking available
Laundry
Kitchen
Air conditioning

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 transportation

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

Smoking not allowed

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)

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

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

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

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

Rogue Valley Intl. Airport (MFR) - 26 min drive

Restaurants

‪Skout Taphouse & Provisions - ‬7 min walk
‪Ruby's - ‬6 min walk
‪RedZone Sports Bar N' Grill - ‬2 min walk
‪Case Coffee Roasters - ‬6 min walk
‪Martolli's Hand Tossed Pizza - ‬6 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 Sept 3, 2025, prices found for a 1-night stay for 2 adults at The Urban Gypsy Loft on Sept 22, 2025 start from CA $165.41, excluding 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?

Check-out 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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The Urban Gypsy Loft Reviews

9.8

Exceptional

10/10

Cleanliness

10/10 Excellent

Christina M.

Apr 7, 2025

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

Jodi A.

Dec 11, 2024

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