The Urban Gypsy Loft
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1 night
1 room, 2 adults, 0 children
All properties in Ashland
The Urban Gypsy Loft
New to Trip.com
Ashland, Oregon 97520, United States
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Amenities
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

- 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. NZD 2.04). Trip Coins can be used to save instantly on room rates.

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.

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.
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.
Cots and Extra Beds
Please contact the hotel for details about cot 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 are the check-in and check-out times at The Urban Gypsy Loft?
The check-in time at The Urban Gypsy Loft is 16:00 and the check-out time is 11:00.What are the check-in and check-out times at The Urban Gypsy Loft?
How much does it cost to stay at The Urban Gypsy Loft?
Prices at The Urban Gypsy Loft are subject to change according to dates, hotel policy, and other factors. To view prices, please search for the dates you wish to stay at the hotel.How much does it cost to stay at The Urban Gypsy Loft?
Which airport is closest to The Urban Gypsy Loft?
Rogue Valley International-Medford Airport is the closest airport to The Urban Gypsy Loft, and it is about 23 mins from hotel by car (26.0 km).Which airport is closest to The Urban Gypsy Loft?
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?
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 |