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The Urban Gypsy Loft

Apartment perfectly located for exploring Historic Downtown District

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Photo gallery for The Urban Gypsy Loft

Fridge, microwave, oven, coffee/tea maker
2 bedrooms, desk, WiFi, bed sheets
Interior
Interior
Interior

Reviews

9.8 out of 10
Exceptional

Entire apartment

2 bedrooms1 bathroom

Popular amenities

  • Parking available
  • Laundry
  • Kitchen
  • Air conditioning

Explore the area

View in a 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

Room options

About the neighborhood

Ashland

Historic Downtown District stay.A stay at this Historic Downtown District apartment places you steps from Ashland Library and within a 5-minute walk of Oregon Cabaret Theatre. Allen Elizabethan Theatre and Angus Bowmer Theatre are also within half a mile (1 km).
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What's nearby

  • Oregon Cabaret Theatre - 3 min walk - 0.2 miles
  • Allen Elizabethan Theatre - 6 min walk - 0.4 miles
  • Oregon Shakespeare Festival - 6 min walk - 0.4 miles
  • Lithia Park - 6 min walk - 0.4 miles
  • Southern Oregon University - 14 min walk - 0.8 miles

Getting around

  • Rogue Valley Intl. Airport (MFR) - 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

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!

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4.8 out of 5, Exceptional, 155 reviews
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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

  • No pets 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
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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Frequently asked questions

How close is The Urban Gypsy Loft to the airport?

This apartment is 16.2 mi (26-min drive) away from the Rogue Valley Intl. Airport (MFR) airport, the closest popular airport to the property.

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

As of Oct 23, 2025, prices found for a 1-night stay for 2 adults at The Urban Gypsy Loft on Oct 26, 2025 start from $108.0, 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.

Does The Urban Gypsy Loft have an airport shuttle?

Airport shuttle services are not available at this apartment.

Does The Urban Gypsy Loft offer free breakfast?

This apartment does not offer free breakfast.

Is there a casino at The Urban Gypsy Loft?

No, there is no casino at this apartment.

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

Check-in begins at 4:00 PM.

Is there free parking at The Urban Gypsy Loft?

Free parking is not available at this apartment.

Does The Urban Gypsy Loft have a pool?

This apartment does not have a pool.

Does The Urban Gypsy Loft have a spa?

There are no spa services available at this apartment.

How close is The Urban Gypsy Loft to downtown Ashland?

This apartment is 0.2 mi away from Ashland.

The Urban Gypsy Loft Reviews

Reviews

9.8

Exceptional

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

10/10

Cleanliness

Reviews

10/10 Excellent

Laurie V.

Liked: Cleanliness
Cozy space located close to theater.
Stayed 3 nights in Sep 2025

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

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