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The Urban Gypsy Loft

Photo gallery for The Urban Gypsy Loft

Enjoy cooking in this well-equipped kitchen with a window, sink, and coffee maker.
Relax in this stylish living room with a round coffee table, green armchairs, and a dining area.
Enjoy a serene view of the surrounding neighborhood from this room's window.
Relax in this inviting living space with a sofa, coffee table, and floor lamp.
Relax in a warm and inviting space with a comfortable bed, floor lamp, and potted plant.

Entire apartment

2 bedrooms1 bathroom

Popular amenities

  • Parking available
  • Laundry
  • Kitchen
  • Air conditioning
The current price is AU$445
includes taxes & fees
7 Aug - 8 Aug

Explore the area

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

Room options

About the area

Ashland

This apartment places you steps from Ashland Library and within a short 5-minute stroll of Oregon Cabaret Theatre. .Apartment features a dining area, a Smart TV and a coffee/tea maker. In-room dining is easy with a kitchen that comes equipped with a fridge and a microwave. A hairdryer and a desk are also available.
View more Apartments in AshlandOpens in a new window

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

  • ‪Skout Taphouse & Provisions - ‬7 min walk
  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪Starbucks - ‬5 min walk
  • ‪Case Coffee Roasters - ‬6 min walk
  • ‪Larks Home Kitchen Cuisine - ‬3 min walk

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 manager

Alisha

Languages

English

Similar properties

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A Cowslip's Belle Inn

  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
4.9 out of 5, Exceptional, 34 reviews
The price is AU$423
includes taxes & fees
4 Aug - 5 Aug
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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)

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

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in all accommodation.

Frequently asked questions

Does The Urban Gypsy Loft have a pool?

No, this apartment doesn't have a pool.

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

As of 31 July 2025, prices found for a 1-night stay for 2 adults at The Urban Gypsy Loft on 7 Aug 2025 start from AU$444.85, 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 The Urban Gypsy Loft family-friendly?

You bet! With amenities such as laundry facilities and children's dinnerware, it's no surprise that The Urban Gypsy Loft is a winner with our family travellers.

Is there a free airport shuttle available at The Urban Gypsy Loft?

No, The Urban Gypsy Loft does not offer an airport shuttle service.

What time are check-in & check-out at The Urban Gypsy Loft?

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Are pets allowed at The Urban Gypsy Loft?

No, pets are not allowed.

The Urban Gypsy Loft Reviews

Reviews

8.6

Excellent

Rating 10 - Excellent. 5 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. 1 out of 7 reviews

8.8/10

Cleanliness

Reviews

10/10 Excellent

Corey L.

Stayed 1 night in Jun 2025

10/10 Excellent

Matt S.

Liked: Cleanliness

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

2/10 Terrible

Richard H.

Disliked: Cleanliness
Avoid this host.My wife and I spent a few hours at the property on the day that we checked in (Tuesday), but when we lay down to rest for the evening, we noticed a bad smell - feces. We sniffed around briefly trying to locate the source of it, but we couldn’t. Disgusted and unwilling to sleep in a bed that smelled of poop, we packed up and headed home, and wrote to the host, Alisha, on the way. Alisha responded the next day claiming that there was no problem, that we were just smelling “natural aromas” from the bakery and restaurant downstairs. She offered a token one-night refund, but I requested a full refund and that she acknowledge the problem and vow to fix it for the next guest. She did not.I assumed at first that Alisha was just a stubborn property owner who refused to admit there could be a problem with her property, but I found out later that there was a plumbing emergency in the building the night before we checked in (the restaurant downstairs had to close for three hours), and Alisha was in the room when the plumber was called. Alisha knew there was a plumbing problem and should have taken our complaint of sewage smells seriously.We’ve reported this incident to Vrbo customer support as a health and safety issue, and are awaiting a resolution. We may or may not receive a refund, but hopefully at least YOU can avoid booking with this dishonest host.
Stayed 2 nights in Jul 2025

8/10 Good

Maureen S.

Liked: Cleanliness

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

Rolanda S.

Liked: Cleanliness

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

Christina M.

Liked: Cleanliness

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., San Jose

Liked: Cleanliness

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