Title: Oak Street Cottages - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Oak Street Cottages Cottages in Ashland with kitchens and patios ## Photo gallery for Oak Street Cottages ![Cottage, Private Bathroom (Oak Hideaway) | Terrace/patio - Oak Street Cottages (Ashland)](https://images.trvl-media.com/lodging/18000000/17420000/17414100/17414099/7d605f34.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Room, Private Bathroom (Oak Lawn) | In-room dining - Oak Street Cottages (Ashland)](https://images.trvl-media.com/lodging/18000000/17420000/17414100/17414099/c3acaed3.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Room, Private Bathroom (Oak Lawn) - Oak Street Cottages (Ashland)](https://images.trvl-media.com/lodging/18000000/17420000/17414100/17414099/d2104a7b.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Room, Private Bathroom (Oak Lawn) | Living area - Oak Street Cottages (Ashland)](https://images.trvl-media.com/lodging/18000000/17420000/17414100/17414099/ea675a3f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Room, Private Bathroom (Sherwin Cottage) | Living room - Oak Street Cottages (Ashland)](https://images.trvl-media.com/lodging/18000000/17420000/17414100/17414099/d644cc84.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Rooms - Location - Policies Oak Street Cottages provides everything you need. Guests can connect to free in-room WiFi. ## Reviews 9.4 Exceptional ## Popular amenities - Pet friendly - Parking included - Free WiFi - Air conditioning - Kitchen ## Room options ### Check availability for these dates Tonight [Jan. 19 - Jan. 20](https://www.expedia.ca/Hotel-Search?startDate=2026-01-19&endDate=2026-01-20&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-19&endDate=2026-01-20&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) Tomorrow [Jan. 20 - Jan. 21](https://www.expedia.ca/Hotel-Search?startDate=2026-01-20&endDate=2026-01-21&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-20&endDate=2026-01-21&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) This weekend [Jan. 23 - Jan. 25](https://www.expedia.ca/Hotel-Search?startDate=2026-01-23&endDate=2026-01-25&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-23&endDate=2026-01-25&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) Next weekend [Jan. 30 - Feb. 1](https://www.expedia.ca/Hotel-Search?startDate=2026-01-30&endDate=2026-02-01&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-30&endDate=2026-02-01&selected=17414099&PinnedHotelID=17414099&HadPinnedHotel=true®ionId=-1&adults=2) ![Mod logo](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Sign in to view eligible discounts and perks. More rewards for more adventures! [Sign in](https://www.expedia.ca/login?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMedford-Hotels-Oak-Street-Cottages.h17414099.Hotel-Information)[Sign up, it's free](https://www.expedia.ca/signup?enable_registration=true&uurl=e3id%3Dredr%26rurl%3D%2FMedford-Hotels-Oak-Street-Cottages.h17414099.Hotel-Information) ## About the area Historic Downtown District, a neighborhood in Ashland, is home to Oak Street Cottages. The area's natural beauty can be seen at North Mountain Park and Cascade-Siskiyou National Monument, while Allen Elizabethan Theatre and Angus Bowmer Theatre are cultural highlights. ScienceWorks Hands-On Museum and The RRRink are also worth visiting. [Visit our Ashland travel guide](https://www.expedia.ca/Ashland.dx6290) [View more Cottages in Ashland](https://www.expedia.ca/Ashland-Cottages.d6290-aaCottages.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C42.19840%2C-122.71440&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=H_ohgOdxCZro12Q0fxmZ9FSJuB4=) 171 Oak Street, Ashland, OR, 97520 ### What's nearby - Allen Elizabethan Theatre \- 2 min walk \- 0.2 km - Lithia Park \- 2 min walk \- 0.2 km - Thomas Theatre \- 2 min walk \- 0.2 km - Oregon Shakespeare Festival \- 3 min walk \- 0.3 km - Oregon Cabaret Theatre \- 5 min walk \- 0.4 km ### Getting around - Rogue Valley Intl. Airport (MFR) - 21 min drive ### Restaurants - ‪Mix Sweet Shop - ‬3 min walk - ‪Martolli's Hand Tossed Pizza - ‬2 min walk - ‪Local 31 Pub - ‬3 min walk - ‪Case Coffee Roasters - ‬3 min walk - ‪Louie's Bar and Grill - ‬3 min walk ## About this property ### Oak Street Cottages Cottage located in Historic Downtown District Oak Street Cottages provides everything you need. Guests can connect to free in-room WiFi. You'll also find perks like: - Free self parking - Barbecue grills Room features All guestrooms at Oak Street Cottages feature perks such as fireplaces and air conditioning, in addition to amenities like free WiFi and separate dining areas. Other conveniences in all rooms include: - Bathrooms with showers - TVs with cable channels and DVD players - Patios, separate dining areas, and kitchens ## Similar properties ![Villa (2 Bedrooms)](https://images.trvl-media.com/lodging/32000000/31900000/31892800/31892740/746d8170.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oak Tower Townhouse-1.5 Blocks to OSF Historic Downtown District - Kitchen - Pet friendly - Parking included - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31892740&PinnedHotelID=31892740&HadPinnedHotel=true®ionId=-1&adults=2) ![Cottage (2 Bedrooms) | Living area](https://images.trvl-media.com/lodging/32000000/31900000/31892900/31892854/f413ca4e.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oak Lawn Cottage \~ 1.5 Blocks to OSF Historic Downtown District - Kitchen - Pet friendly - Parking included - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31892854&PinnedHotelID=31892854&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property](https://images.trvl-media.com/lodging/32000000/31620000/31612600/31612561/0ee13dc4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oak Hideaway Cottage- 1.5 Blocks to OSF Historic Downtown District - Kitchen - Parking included - Free WiFi - Barbecue grill [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31612561&PinnedHotelID=31612561&HadPinnedHotel=true®ionId=-1&adults=2) ![House (2 Bedrooms) | Living area](https://images.trvl-media.com/lodging/32000000/31620000/31612600/31612560/cab18a77.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oak Sherwin House Near OSF Historic Downtown District - Kitchen - Parking included - Free WiFi - Outdoor Space [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31612560&PinnedHotelID=31612560&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property](https://images.trvl-media.com/lodging/32000000/31620000/31611500/31611461/cffaff50.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Pioneer Craftsman House - Closest to Osf Historic Downtown District - Kitchen - Washer - Dryer - Parking included [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31611461&PinnedHotelID=31611461&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property](https://images.trvl-media.com/lodging/32000000/31620000/31611600/31611561/890dee14.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pioneer House - North Suite Historic Downtown District - Kitchen - Washer - Dryer - Parking included [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31611561&PinnedHotelID=31611561&HadPinnedHotel=true®ionId=-1&adults=2) ![House (3 Bedrooms) | Living area](https://images.trvl-media.com/lodging/32000000/31620000/31612500/31612463/9a8491be.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pioneer House - South Suite Historic Downtown District - Kitchen - Washer - Dryer - Parking included [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31612463&PinnedHotelID=31612463&HadPinnedHotel=true®ionId=-1&adults=2) ![House (2 Bedrooms) | Terrace/patio](https://images.trvl-media.com/lodging/32000000/31620000/31611600/31611549/f53612b9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lori Lanes 'romeo Cottage' \~ 2 Bedroom \~ Downtown Ashland - Kitchen - Parking included - Free WiFi - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=31611549&PinnedHotelID=31611549&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95270000/95265600/95265593/4a0948e6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### A Cowslip's Belle Inn Ashland - Pet friendly - Parking included - Free WiFi - Air conditioning 9.8 Exceptional 40 reviews CA $188 CA $287 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-20&endDate=2026-01-21&selected=95265593&PinnedHotelID=95265593&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/113000000/112020000/112015600/112015563/696d0207.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Charming carriage house in Ashland near downtown Skidmore Academy Historic District - Washer - Dryer - Pet friendly - Air conditioning 10 Exceptional 6 reviews CA $144 CA $288 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-20&endDate=2026-01-21&selected=112015563&PinnedHotelID=112015563&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in start time: 4 PM; Check-in end time: 7 PM ### Check-out Check-out before 10 AM ### Special check-in instructions Information provided by the property may be translated using automated translation tools ### Pets Pets allowed for an extra charge of USD 50 per pet, per stay Service animals are welcome, and are exempt from fees Restrictions apply; for more information contact the property at the number on the booking confirmation ### Children and extra beds Children are welcome Rollaway/extra beds are not available Free cribs are available on request at the property ### Property payment types ## Important information ### Fees You'll be asked to pay the following charges at the property. Fees may include applicable taxes: - Deposit: USD 250.00 per stay We have included all charges provided to us by the property. ### Optional extras - Pet fee: USD 50 per pet, per stay - Service animals are exempt from fees - Housekeeping fee: USD 125 per stay The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change. ### You need to know 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 This property accepts credit cards Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property ### Property is also known as Oak Street Cottages B&B Ashland Oak Street Cottages B&B Oak Street Cottages Ashland Oak Street Cottages House Ashland Oak Street Cottages House Ashland Oak Street Cottages House Oak Street Cottages Ashland Cottage Oak Street Cottages Ashland Ashland Oak Street Cottages Cottage Cottage Oak Street Cottages Oak Cottages House Ashland Oak Street Cottages Cottage Oak Street Cottages Ashland Oak Street Cottages Cottage Ashland ## Frequently asked questions ### Is Oak Street Cottages pet-friendly? ### How much is parking? ### What time is check-in at Oak Street Cottages? ### What time is check-out at Oak Street Cottages? ### Where is Oak Street Cottages located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Reviews ## Oak Street Cottages Reviews 9.4 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 9.4 Cleanliness ### 9.4 Staff & service ### 9.4 Property conditions & facilities 10 - Excellent 2 8 - Good 1 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ## Reviews ### 10/10 Excellent #### Wendy, CA Jul 4, 2018 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Clean, Comfortable, Gracious Right in the heart of Ashland and only a block from the Oregon Shakespeare Festival this place is a gem. We stayed in the Oak Tower suite, a two story, could sleep 8 accommodation. Not only was it immaculate but it was sweetly appointed with fresh flowers, contemporary magazines, fresh fruit, Martinelli's Cider and popcorn. Master bedroom and second bedroom, large second bedroom and huge bathroom with Jacuzzi tub on the entrance level. Large living room, dining room, second bathroom and full kitchen on the second. Outdoor deck included a gas grill, table and chairs. ##### Wendy Stayed 4 nights in Jun 2018 ### 8/10 Good #### Verified traveller May 15, 2018 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort Wonderful location, comfortable beds, love the sinks in the bedrooms ##### Verified traveller Stayed 3 nights in May 2018 ### 10/10 Excellent #### Verified traveller Apr 20, 2018 Liked: Cleanliness, staff & service, property conditions & facilities, room comfort #### Charming Accomodaitons in Great Location We loved our stay here. The house was so comfortable, spotless, fully equipped and outfitted with everything we could have needed, and walking distance to all the places we wanted to go in town. Would definitely stay here again and recommend it highly. ##### Verified traveller Stayed 3 nights in Apr 2018 ## Expedia's Latest Trends ### Hotels > [Staypineapple, Hotel Rose, Downtown Portland](https://www.expedia.ca/Portland-Hotels-Staypineapple.h440831.Hotel-Information) > > [Hotel Vance, Portland, a Tribute Portfolio Hotel](https://www.expedia.ca/Portland-Hotels-Hotel-Vance.h30039520.Hotel-Information) > > [Hallmark Resort - Cannon Beach](https://www.expedia.ca/Cannon-Beach-Hotels-Hallmark-Resort-Cannon-Beach.h5431022.Hotel-Information) > > [University Place Hotel & Conference Center](https://www.expedia.ca/Portland-Hotels-University-Place-Hotel-Conference-Center.h17920.Hotel-Information) > > [Jupiter Hotel](https://www.expedia.ca/Portland-Hotels-Jupiter-Hotel.h1062725.Hotel-Information) > > [Moxy Portland Downtown](https://www.expedia.ca/Portland-Hotels-Moxy-Portland-Downtown.h61340845.Hotel-Information) > > [The Duniway Portland A Hilton Hotel](https://www.expedia.ca/Portland-Hotels-The-Duniway-Portland-A-Hilton-Hotel.h17395433.Hotel-Information) > > [The Porter Portland, Curio Collection by Hilton](https://www.expedia.ca/Portland-Hotels-The-Porter-Portland.h21728839.Hotel-Information) > > [Hampton Inn & Suites Portland-Pearl District](https://www.expedia.ca/Portland-Hotels-Hampton-Inn-And-Suites-By-Hilton-Portland-Pearl-District.h18754357.Hotel-Information) > > [Heathman Hotel](https://www.expedia.ca/Portland-Hotels-The-Heathman-Hotel.h3096.Hotel-Information) > > [Surfsand Resort](https://www.expedia.ca/Cannon-Beach-Hotels-Surfsand-Resort.h9753263.Hotel-Information) > > [Mark Spencer Hotel](https://www.expedia.ca/Portland-Hotels-Mark-Spencer-Hotel.h19921.Hotel-Information) > > [Hilton Portland Downtown](https://www.expedia.ca/Portland-Hotels-Hilton-Portland-Downtown.h25551.Hotel-Information) > > [The Nines, a Luxury Collection Hotel, Portland](https://www.expedia.ca/Portland-Hotels-The-Nines.h2140707.Hotel-Information) > > [Tolovana Inn](https://www.expedia.ca/Cannon-Beach-Hotels-Tolovana-Inn.h1094927.Hotel-Information) > > [Hyatt Regency Portland at the Oregon Convention Center](https://www.expedia.ca/Portland-Hotels-Hyatt-Regency-Portland-At-The-Oregon-Convention-Center.h39915679.Hotel-Information) > > [Abigail’s Bed & Breakfast Inn](https://www.expedia.ca/Medford-Hotels-Abigails-Bed-Breakfast-Inn.h4966403.Hotel-Information) > > [The Hotel Zags Portland](https://www.expedia.ca/Portland-Hotels-The-Hotel-Zags-Portland.h22135.Hotel-Information) > > [Hyatt House Portland/Downtown](https://www.expedia.ca/Portland-Hotels-Hyatt-House-PortlandDowntown.h15490291.Hotel-Information) > > [Homewood Suites by Hilton Vancouver-Portland](https://www.expedia.ca/Portland-Hotels-Homewood-Suites-By-Hilton-Vancouver-Portland.h62858.Hotel-Information) > > [Crowne Plaza Portland Downtown Convention Center by IHG](https://www.expedia.ca/Portland-Hotels-Crowne-Plaza-Portland-Downtown-Convention-Center.h40665.Hotel-Information) > > [Dossier Hotel](https://www.expedia.ca/Portland-Hotels-Dossier.h285371.Hotel-Information) > > [Courtyard by Marriott Portland City Center](https://www.expedia.ca/Portland-Hotels-Courtyard-By-Marriott-Portland-City-Center.h2469036.Hotel-Information) > > [The Benson Portland, Curio Collection by Hilton](https://www.expedia.ca/Portland-Hotels-The-Benson.h28272.Hotel-Information) > > [Hotel Lucia](https://www.expedia.ca/Portland-Hotels-Hotel-Lucia.h15988.Hotel-Information) > > [Hotel deLuxe](https://www.expedia.ca/Portland-Hotels-Hotel-DeLuxe.h37645.Hotel-Information) > > [The Paramount Hotel](https://www.expedia.ca/Portland-Hotels-The-Paramount-Hotel.h330558.Hotel-Information) > > [Embassy Suites by Hilton Portland Downtown](https://www.expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Downtown.h74615.Hotel-Information) > > [The Royal Sonesta Portland Downtown](https://www.expedia.ca/Portland-Hotels-Royal-Sonesta-Portland.h41174.Hotel-Information)