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Oak Street Cottages

Downtown Ashland

The Oak Street Cottages are located in the heart of downtown Ashland, just one and a half blocks from the famed Oregon Shakespeare Festival. These homes are the perfect choice for large groups and those looking to park the car and enjoy an Ashland getaway on foot.

Oak Street - Sherwin House>

Just steps from OSF

Built in the late 1800s, the Sherwin House is located in the heart of downtown Ashland, just one and a half blocks from the famed Oregon Shakespeare Festival. The perfect choice for large groups and those looking to park the car and enjoy an Ashland getaway on foot.

 The Space

Located at the front of the property the Sherwin House features a full kitchen, front yard with BBQ and comfortable outdoor seating, two private bedrooms, two full bathrooms, large jacuzzi tub and space enough to accommodate up to 11 guests. The house shares an adjacent wall with one of several cottages located on the same property.

Interaction with Guests

Guest have full access to the property. You'll have all the privacy you need on site unless of course, you need us. We are located close by and are always available to assist our guests with making plans for theater, restaurants, shopping, wine tasting, hiking, water sports, and so much more!


Prices start at $325.00

 

For information on Travel Occupancy Tax, please follow link here.

Amenities

  • Private Parking
  • Full Kitchen
  • Wireless Internet
  • Flat Screen Television
  • Cable TV
  • Fireplace
  • Heat and Air Conditioning
  • Laptop Friendly Workspace
  • Kitchen Essentials
  • Bathroom Essentials
  • Iron and Ironing Board
  • Outdoor Seating and BBQ
  • Pets Allowed
    • Approval Required
    • $125 Cleaning Fee
Book Now

Oak Hideaway Cottage>

1.5 Blocks To Oregon Shakespeare Festival

Located in the heart of downtown Ashland, the Hideaway Cottage is situated just one and a half blocks from the famed Oregon Shakespeare Festival. The perfect choice for those looking to park the car and enjoy an Ashland getaway on foot, this cottage can also be rented with the other homes on site to comfortably accommodate larger groups.


The Space

The home features a full kitchen, generous living room with fireplace, flat panel television, a patio with BBQ and seating, two private bedrooms, full bathroom, and enough sleeping space to accommodate up to 6 guests. The cottage is located on the same property as several other rentals and shares an adjacent wall with another cottage.


Interaction with Guests

Guest have full access to the property. You'll have all the privacy you need on site unless of course, you need us. We are located close by and are always available to assist our guests with making plans for theater, restaurants, shopping, wine tasting, hiking, water sports, and so much more!

 Prices start at $265.00

 

For information on Travel Occupancy Tax, please follow link here.

Amenities

  • Private Parking
  • Full Kitchen
  • Wireless Internet
  • Flat Screen Television
  • Cable TV
  • Fireplace
  • Heat and Air Conditioning
  • Laptop Friendly Workspace
  • Kitchen Essentials
  • Bathroom Essentials
  • Iron and Ironing Board
  • Outdoor Seating and BBQ
  • Pets Allowed
    • Approval Required
    • $100 Cleaning Fee
Book Now

Oak Lawn Cottage>

1.5 Blocks to OSF

Located in the heart of downtown Ashland, the Oak Lawn Cottage is situated just one and a half blocks from the famed Oregon Shakespeare Festival. The perfect choice for those looking to park the car and enjoy an Ashland getaway on foot, this cottage can also be rented with the other homes on site to comfortably accommodate larger groups.


The Space

The home features a full kitchen, generous living room with fireplace, flat panel television, a patio with BBQ and seating, two private bedrooms, full bathroom, and enough sleeping space to accommodate up to 6 guests. The cottage is located on the same property as several other rentals and shares an adjacent wall with another cottage.


Interaction with Guests

Guest have full access to the property. You'll have all the privacy you need on site unless of course, you need us. We are located close by and are always available to assist our guests with making plans for theater, restaurants, shopping, wine tasting, hiking, water sports, and so much more!


Prices start at $265.00

 

For information on Travel Occupancy Tax, please follow link here.

Amenities

  • Private Parking
  • Full Kitchen
  • Wireless Internet
  • Flat Screen Television
  • Cable TV
  • Fireplace
  • Heat and Air Conditioning
  • Laptop Friendly Workspace
  • Kitchen Essentials
  • Bathroom Essentials
  • Iron and Ironing Board
  • Outdoor Seating and BBQ
  • Pets Allowed
    • Approval Required
    • $100 Cleaning Fee
Book Now

Oak Tower Townhouse>

1.5 Blocks to OSF

Located in the heart of downtown Ashland, the Oak Tower Townhouse is situated just one and a half blocks from the famed Oregon Shakespeare Festival. The perfect choice for those looking to park the car and enjoy an Ashland getaway on foot, this cottage can also be rented with the other homes on site to comfortably accommodate larger groups.


The Space

The home features a full kitchen, a patio with BBQ and outdoor seating, two private bedrooms, and enough sleeping space to accommodate a total of 8 guests. There are two full bathrooms, one with shower and one with a large double jacuzzi tub. The cottage is located at the rear of the property and shares an adjacent wall with another cottage.


Interaction with Guests

Guest have full access to the property. You'll have all the privacy you need on site unless of course, you need us. We are located close by and are always available to assist our guests with making plans for theater, restaurants, shopping, wine tasting, hiking, water sports, and so much more!

Prices start at $285 

 

For information on Travel Occupancy Tax, please follow link here.

Amenities

  • Private Parking
  • Full Kitchen
  • Wireless Internet
  • Flat Screen Television
  • Cable TV
  • Fireplace
  • Heat and Air Conditioning
  • Laptop Friendly Workspace
  • Kitchen Essentials
  • Bathroom Essentials
  • Iron and Ironing Board
  • Outdoor Seating and BBQ
  • Pets Allowed
    • Approval Required
    • $125 Cleaning Fee
Book Now

Oak Street - Studio>

Just steps from OSF

Built in the late 1800s, the Sherwin House is located in the heart of downtown Ashland, just one and a half blocks from the famed Oregon Shakespeare Festival. The perfect choice for large groups and those looking to park the car and enjoy an Ashland getaway on foot.

 The Space

Located at the front of the property the Water Suite features a kitchenette, one private bedroom with a king-size bed, a queen sofa pullout, one full bathroom, and space enough to accommodate up to 4 guests. The house shares an adjacent wall with one of several cottages located on the same property.

Interaction with Guests

Guest have full access to the property. You'll have all the privacy you need on site unless of course, you need us. We are located close by and are always available to assist our guests with making plans for theater, restaurants, shopping, wine tasting, hiking, water sports, and so much more!


Prices start at $135.00

 

For information on Travel Occupancy Tax, please follow link here.

Amenities

 

  • Private Parking
  • One Bedroom
    • King-size Bed
  • Kitchenette
    • Fridge
    • Microwave
    • Coffee Maker
  • Wireless Internet
  • 50" 4K Smart TV
  • Heat and Air Conditioning
  • Laptop Friendly Workspace
  • Sleeper Sofa w/Chaise
  • Kitchen Essentials
  • Bathroom Essentials
  • Iron and Ironing Board
  • Pets Allowed
  • $50 Cleaning Fee
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