The Urban Gypsy Loft
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1 night
1 room, 2 adults, 0 children
All properties in Ashland
The Urban Gypsy Loft
Ashland, Oregon, 97520
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Highlights
Ideal location
Sparkling clean
Excellent serviceAmenities
No smoking in public areas
Clothes dryer
All amenities
Property Description
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!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Do not use fireplace, not a working fireplace.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
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10.0/10
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 5 reviews
Surroundings
Airport: Rogue Valley International-Medford Airport
(26.0 km)
Train: Ronkonkoma Station
(21.2 km)
Train: Medford LIRR Station
(21.2 km)
Landmarks: Trinity Episcopal Church
(110m)
Landmarks: Oregon Cabaret Theatre
(190m)
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Overview
Rooms
Guest Reviews
Services & Amenities
Policies
Host
8
Two-Bedroom Apartment
2 bedrooms: 2 king beds
Non-smoking
Air conditioning
Refrigerator
TV
Desk
Check Availability
Guest Reviews
10.0/10
Outstanding
5 reviews
Verified Reviews- Cleanliness10.0
- Amenities10.0
- Location10.0
- Service10.0
Average for similar properties in Ashland
Book now and leave a review after your stay to earn up to 120 Trip Coins (approx. US$1.20). Trip Coins can be used to save instantly on room rates.
Matt S.
July 19, 2025
Shakespeare in Ashland
Property is well placed for walking to the theater's, restaurants and core town downtown shops.
Maureen S.
June 29, 2025
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.
Rolanda S.
June 20, 2025
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
Jodi A.
December 12, 2024
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.
Christina M.
April 8, 2025
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.
Services & Amenities
More Amenities
Public Areas
No smoking in public areas
Cleaning Services
Clothes dryer
Property Policies
Check-in and Check-out Times
Check-in: after 16:00
Check-out: Before 11:00
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.
Cribs and Extra Beds
Please contact the hotel for details about crib and extra bed policies.
Property host
Alisha
Speaks: English
About this property
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!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Do not use fireplace, not a working fireplace.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
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Frequently Asked Questions
What is the cancellation policy for The Urban Gypsy Loft?
The cancellation policy for The Urban Gypsy Loft varies depending on the type of room and booking conditions.What is the cancellation policy for The Urban Gypsy Loft?
What are the check-in and check-out times at The Urban Gypsy Loft?
Standard check-in time at The Urban Gypsy Loft is 16:00 and check-out time is 11:00.What are the check-in and check-out times at The Urban Gypsy Loft?
How far is the The Urban Gypsy Loft from the closest airport?
The closest airport is Rogue Valley International-Medford Airport, and it is about 23 mins from hotel by car (26.0 km).How far is the The Urban Gypsy Loft from the closest airport?
About This Property
| Nearest Airport | Rogue Valley International-Medford Airport |
|---|---|
| Distance to Airport | 25.97KM |
| Nearest Train Station | Ronkonkoma Station |
| Distance to Train Station | 21.16KM |
| Hotel Star Rating | 4 |