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The Urban Gypsy Loft

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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
  • 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

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Property grounds

The Maple Apartment at Tudor House Vacation Rentals

  • Kitchen
  • Air conditioning
  • Outdoor space
  • Parking available
4.8 out of 5, Exceptional, 151 reviews
The Maple Apartment at Tudor House Vacation Rentals

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!
During your stay at this apartment building, you're just a quick walk from Ashland Library. Features include laundry facilities. Enjoy your stay with amenities like a kitchen and a Smart TV in the apartment.
  • Air-conditioned apartment with kitchen, dining area, and Smart TV
  • Amenities include laundry facilities
  • Steps from Ashland Library and 4 minutes by foot from Oregon Cabaret Theatre
This apartment offers its guests laundry facilities. The front desk is open around the clock.

This Ashland apartment is smoke free.

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

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

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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

The Urban Gypsy Loft Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 5 out of 6 reviews
Rating 8 - Good. 1 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

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

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