Helman Street Penthouse with a View
House in Ashland, OR
4 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
High-end valuePrice for this property is higher than average in the area
About this house rental
This award winning building is located in Ashland's Historic railroad district just 3 blocks to Ashland's Plaza.
A light and airy second floor, the private penthouse offers an open floor plan, hardwood floors, 2 bedrooms, 2 full bathrooms, an office, a private single car garage, and a large private deck with great views!
The fully equipped kitchen offers everything, marble countertops, and top notch appliances.
A light and airy second floor, the private penthouse offers an open floor plan, hardwood floors, 2 bedrooms, 2 full bathrooms, an office, a private single car garage, and a large private deck with great views!
The fully equipped kitchen offers everything, marble countertops, and top notch appliances.
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Map of Ashland, OR
$$$$
Reviews
5.0
The penthouse was bright, airy, and private. It was impeccably clean, and located close to downtown. We had a marvelous stay.
5.0
My friends and I had a wonderful stay. The location is perfect to walk everywhere. We went into town to shop, eat, see Shakespeare. We enjoyed high tea and a concert in the park.
The house was perfect. There were three of us and we had everything we needed for a great stay. There is no question we would stay again. Thank you for taking such great care of us. We loved your home
5.0
We stayed 2 nights at the Penthouse and it was just perfect. The home is clean, nicely decorated, and close to town. We walked to town more than once. We have family in Ashland and this is where we will stay when we return.
5.0
Lovely time Kristen! Center view window shade doesn't lower ... seems stuck and I didn't want to work it out (engineer in me!!).
Otherwise - Wonderful stay.
I recognized your name from the family construction company in Ashland. Small world indeed. I'll be back!
Catherine Mater
5.0
The Helman Street Penthouse was perfect for our girlfriend's retreat. The home is clean, beautifully decorated and had all the necessary amenities. We were able to walk to all the shops, restaurants and Shakespeare plays. I definitely would recommend staying here during your visit to Ashland.
5.0
plenty of room for two couples to cook , eat and talk but separated sleeing and bathroom areas. Lovely deck.
5.0
We had a wonderful stay at Kristin’s penthouse apartment. Beautifully decorated and the kitchen as well stocked with everything you need for meal preparation. Plenty of room to relax on comfortable furniture and we especially enjoyed dining on the rooftop deck.
Easy walking distance to downtown Ashland and the Oregon Shakespeare Festival. One of our best VRBO experiences.
5.0
A great girlfriend getaway option. Spacious, clean, comfortable and the rooftop deck was perfect for morning coffee, afternoon reading and happy hours. Split bedrooms and a nice layout and fully equipped kitchen are really lovely. Highly recommend!
5.0
Our second stay at Kristin's lovely Penthouse with a View was just as wonderful as our first.
Everything about this stay is top notch. Kristin is easy and communicates extremely well. The unit is spotless and clever, and decorated beyond most short stay units. It is comprised of a large master bedroom with very large bath and a second - still large 2nd BR. The accompanying bath is not technically en-suite, but is as close to being so as can be, around a corner and down a small hallway. Two couples feel very private.
Walking distance to OSF and downtown restaurants, and Lithia Park. It's a real pleasure to arrive, park, and not use the car again until we head home.
This was our second stay...it will not be our last.
5.0
This large, well-appointed rental was a great spot for a long weekend visiting the Oregon Shakespeare Festival and taking advantage of the outdoor activities in and around Ashland. The two bedrooms are on separate ends of the unit and the large kitchen is very well appointed. We made liberal use of the outdoor dining area and grill. The location is perfect, just outside the downtown core, a 10 to 15 minute walk to the theatres and restaurants. Highly recommended!
5.0
This is a lovely place to stay, particularly for two couples who appreciate comfortable bedrooms/baths and well-appointed and spacious living spaces. Even in October, we enjoyed having our breakfasts out on the deck. Since we were in Ashland to see plays, it was great being just a short walk away from the theaters. We would definitely stay here again!
5.0
We have stayed in a few different places in Ashland. This place was the best. It was immaculate, comfortable and beautiful..an easy walk to the coop, to theaters and to restaurants and cafes. The owner provided complete details for arrival and departure…would gladly stay here again.
5.0
Beautiful penthouse with a lovely rooftop patio. Well equipped with even an espresso machine. Very responsive host. Walking distance to everything.
5.0
Super clean, super comfy. We loved being able to use the garage door opener while we stayed. . The house is upstairs and they have a great second floor patio. Nice laundry machines. Nice linens and beds. Beautiful hardware and lighting throughout the house.
It’s very close to downtown. It was a great place to stay while dropping off our son for school at SOU. I can’t think of anything that wasn’t readily available. Great house.
5.0
Great property - Spacious, airy, well equipped, immaculate! Easy walk to town and some great restaurants. Lovely walk by the railroad track each morning. No train noise throughout our entire 3 day stay! 👍👍😀😀
2.5
First, the host is great. Excellent communication and easy to work with! That sets the stage for a great visit. The penthouse is in an ideal location, only a few easy walking blocks from downtown and OSF. Parked the car and left it there the entire visit.
Layout of the unit is ideal for two couples, with bedrooms on opposite sides of the living room/kitchen. The rooftop deck is great, and it even has a one car garage! Rarely have we rented a vacation home so well put together, or so well decorated. Care has been given to the tiniest details; we found fresh half & half and coffee waiting in the fridge! Beds are comfortable, towels are plush and the entire experience was outstanding. TVs are high quality (but, we only used it to look at some vacation photos...didn't need TV with live theatre just around the corner).
We are two couples who come to Ashland for OSF and we'll definitely stay here again.
5.0
One of the nicest VRBO visits we have had. The unit was sparkling clean, with lots of towels, soaps, etc. Communication with the owner, Kristin, was quick and easy. The unit is the top floor of a 2 story building. The offices downstairs were totally quiet, and we had 100% privacy. Huge master bedroom and master bath, nice second bedroom and second bath, beautifully equipped kitchen, very comfortable living and dining space, and a great outside deck with sunshade and gas grill. Thankfully, the unit is air conditioned, and it was totally comfortable in 100 degree heat. Located just a five minute walk from downtown, it is a perfect destination. When we return to Ashland, this will be our first choice!
5.0
Views for days
This spot easily accommodated our group of four. There are many areas to spend time, play games and gather. The kitchen is well equipped for meal preparations
The insta hot tap is an nice perk
5.0
Simply the Best
This was our 2nd visit to this wonderful VRBO! It never disappoints!
So beautiful and they have thought of everything you might need while on Vacation. Tried to book again for Feb. but it's unavailable... 😔 We will definitely miss our “home away from home”!
5.0
Amazing spot.. and penthouse
Everything was great. Definitely coming back.
5.0
Love this property!!
Great location.. beautiful apartment with all the perks. Don’t miss out on this one. We enjoyed the rooftop patio.
5.0
I will definitely be returning! :)
I loved everything about this property. The house is beautiful and filled with light. It has been well taken care of. All the amenities I could ask for. The neighborhood was peaceful (minus one train), and in an excellent location close to town, but not too close. The owner was very flexible regarding check-in time, and I walked into delicious chocolate. I didn't want to leave! :) Another stay is in my future. This property and property owner experience went beyond my expectations!
5.0
Helman townhome
Beautiful top floor townhome, extremely spacious and filled with natural light throughout. Location is excellent, less than ten minute walk to the heart of Ashland. Nicely furnished. Great views throughout. Huge walk in closets, huge master bath with heated floor. Very impressive collection of books to enjoy. Floor plan very well set up with the two bedrooms at opposite ends of the layout. Even though close to Ashland (and its many excellent restaurants), many dinners can be and were spent on balcony with the amazing views. We will definitely be back! Kristin was very responsive.
5.0
Hellman House exceeded our expectations!
This property is absolutely stunning!! They thought of every little detail for their guests! The kitchen is fully stocked with high end appliances, there's a toaster oven, cappuccino machine, a French press for coffee, a blender, coffee, creamer and tea!
Two bouquets of fresh flowers and chocolate! The beds and linens were superb! Extra pillow, blankets and towels!!
Access to the garage is very nice!! Close to downtown! Every-time we returned to the unit we just kept saying how nice our accommodations were! The deck is gorgeous and the office was a bonus for those of us who had to do a bit of work while on vacation!! There is a train but we found it charming and it only went by twice!!
5.0
Better than expected
This upstairs unit was amazing. The house was incredibly clean and conveniently located within walking distance to downtown shops and restaurants. Can’t say enough about the little touches that made our experience unforgettable. We had fresh cut flowers waiting for us (and not just one bouquet)... Delicious chocolate bars, fresh (brand new) coffee and a new carton of real half-and-half waiting in the refrigerator. Lots of amenities in the kitchen including a blender which worked well for margaritas , A microwave toaster oven plenty of pots and pans sharp knives and basic seasonings. We cooked a meal and ate on the rooftop deck. After a day of walking around Ashland we enjoyed hanging out at the home and watching Netflix movies . The towels were clean, fresh and fluffy... and they have gone the extra mile including hairdryers, a clothes steamer, make up wipes, shampoo, conditioner, bath gel and lotion... The master suite was incredible: Giant soaking tub, comfy king bed, and large TV. Went with my sister for a girls weekend - but would certainly recommend this as a great couples getaway. Can’t wait to come back!
5.0
Beyond expectations!
Easy walk to restaurants and shopping. Decor was modern/eclectic, very clean, everything you need for a getaway. We both felt it is underpriced, will stay again. Thank you Kristin
5.0
Helman Penthouse is wonderful!
The Helman Penthouse is a wonderful place to stay. It can easily accommodate 4 people. The host is willing to go out of her way to accommodate the condo guests. There are many amenities in the condo, more than are listed on VRBO. There is a parking garage; the garage door opener was on the kitchen counter. We arrived to find flowers in the kitchen and on the dining room table. There were also chocolate bars on the counter along with coffee and half & half in the refrigerator. These were welcome touches. There is a large flat screen TV in the living room and another in the master bedroom. The TV is not connected to cable TV but you can watch Netflix or Hulu; passwords are provided.
5.0
Beautiful
The property was beautiful, light, and immaculately clean. The host went above and beyond by leaving us a personalized welcome card, chocolates, coffee, and fresh flowers. The beds were comfortable, and the rooftop patio was a wonderful place to relax. In the interest of full disclosure, the house is right next to the train tracks, but during our 3 day stay the train only went by once. Overall the property was amazing and the host was very easy to work with. We would definitely stay there again.
FAQs
How much does this house cost compared to others in Ashland?
The average price for a rental in Ashland is $161 per night. This rental is $234 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Helman Street Penthouse with a View. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Helman Street Penthouse with a View pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Helman Street Penthouse with a View?
We found 9 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and parking.
Explore similar vacation rentals in Ashland
Explore all rentals in Ashland
Railroad District, steps to downtown, everything you need to enjoy Ashland!
House
in Ashland5 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for a memorable stay in Ashland? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.
$$$$
1907 Charmer, Perfect Downtown Location, So Clean!
House
in Ashland8 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Ashland? Look no further than our House, 1907 Charmer, Perfect Downtown Location, So Clean!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown
House
in Ashland10 guests · 5 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
House in Ashland, for $345 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Premier Downstairs Flat in Perfect Down Town Location
House
in Ashland8 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Enjoy the best of Ashland in our House, Premier Downstairs Flat in Perfect Down Town Location . A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland
House
in Ashland6 guests · 3 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
Experience vacation in Ashland with our House, Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Serenity Awaits: Pool, Hot Tub, Sauna, Gym
House
in Ashland10 guests · 4 bedrooms · 4 baths
Garden · Pool · Pets allowed
Enjoy the best of Ashland in our House, Serenity Awaits: Pool, Hot Tub, Sauna, Gym. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Spacious B Street Beauty, Around the Corner from Festival
House
in Ashland10 guests · 3 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Ashland in our House, Spacious B Street Beauty, Around the Corner from Festival. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Abigail's Vacation Cottage private two bedroom & within walking distance to town
Cottage
in Ashland4 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
This attractive Cottage in Ashland, $367 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Luxury condo with king bedroom, two bathrooms, full kitchen.
Apartment
in Ashland4 guests · 1 bedroom · 2 baths
Kitchen or Kitchenette · Air conditioner · Fireplace
Looking for a Apartment in Ashland, this Apartment for $333 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Urban Oasis: Ashland's Premier Location
House
in Ashland16 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
This inviting House in Ashland can fit your needs for many types of vacations, at $371 per night.
$$$$
Luxury condo with king bedroom, two bathrooms, full kitchen.
Apartment
in Ashland4 guests · 1 bedroom · 2 baths
Kitchen or Kitchenette · Air conditioner · Fireplace
Looking for the perfect place to call home during your trip to Ashland? This Apartment offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Kitchen or Kitchenette, and more.
$$$$
Start earning One Key rewards
Dreamy 4BR Sanctuary: Pool, Hot Tub, Gym
House
in Ashland12 guests · 5 bedrooms · 5 baths
Garden · Pool · Pets allowed
Business stays, family stays, couples stay, getaway vacation, and rental in Ashland at Dreamy 4BR Sanctuary: Pool, Hot Tub, Gym for $420 for your next trip.
$$$$
Swank House on Main St in Ashland
House
in Ashland4 guests · 2 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for the perfect place to call home during your trip to Ashland? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.
Apartment
in Ashland6 guests · 2 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Fireplace
Nestled in Ashland, this Apartment is perfect for your next vacation. Enjoy Luxury condo with 2 bedrooms/2 bathrooms, sleeper sofa, full kitchen.'s top-rated amenities, including Air conditioner, Fireplace and Kitchen or Kitchenette, and more.
$$$$
Mountain Ave House by WanderLodges
House
in Ashland6 guests · 3 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for a House in Ashland, this House for $331 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Updated 3BR Escape: Valley Views, Pet-Friendly
House
in Ashland5 guests · 3 bedrooms · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette
This attractive House in Ashland, $342 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
2 Budget Friendly Rooms, Scottish Inns, Near Southern Oregon University
House
in Ashland8 guests · 2 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Discover the beauty of Ashland with a stay at 2 Budget Friendly Rooms, Scottish Inns, Near Southern Oregon University, a top rated House with amenities such as Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.
$$$$
2-story, 3 bedroom modern home with king and queen beds, living room and kitchen.
Apartment
in Ashland8 guests · 3 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner
Apartment in Ashland, for $361 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Ashland travel inspiration
Read our blogGuides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
Keep exploring
- Kauai Villas
- Orlando Villas
- Kiawah Island Villas
- Miami Beach Villas
- Kissimmee Villas
- North Naples Villas
- Florida Keys Villas
- Phoenix Villas
- Los Angeles Villas
- St Petersburg Villas
- Palm Desert Villas
- Miami Villas
- Las Vegas Villas
- Venice Villas
- Key West Villas
- Palm Springs Villas
- Lake Tahoe Villas
- Hollywood Hills Villas
- Seabrook Island Villas
- South Lake Tahoe Villas
- Pocono Mountains Villas
- Scottsdale Villas
- Myrtle Beach Villas
- Hilton Head Island Villas
- Marco Island Villas
- North Miami Villas
- Sanibel Island Villas
- West Palm Beach Villas
- Fort Myers Beach Villas
- Haines City Villas
- North Las Vegas Villas
- Destin Villas
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals