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Entire apartment

The Urban Gypsy Loft

Apartment in Ashland with kitchen

Photo gallery for The Urban Gypsy Loft

Fridge, microwave, oven, coffee/tea maker
Interior
Interior
2 bedrooms, desk, WiFi, bed sheets
Interior
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 NZ$449
includes taxes & fees
16 Nov - 17 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, 155 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

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

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
  • ‪Zoey's Cafe - ‬3 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 Nov 2025, prices found for a 1-night stay for 2 adults at The Urban Gypsy Loft on 16 Nov 2025 start from NZ$449.45, 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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Reviews

The Urban Gypsy Loft Reviews

9.8

Exceptional

10

Cleanliness

10

Location
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

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