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Reviews of Second Street Cottages

144 North Second Street, Ashland, OR 97520, United States

#1 of 10 Holiday rentals in Ashland

Guests' Choice

Review score

Based on 44 hotel reviews

9.8

Score breakdown

  • Cleanliness

    9.9

  • Comfort

    9.9

  • Location

    10.0

  • Facilities

    10.0

  • Staff

    10.0

  • Value for money

    9.5

  • Free WiFi

    10.0

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Showing 1 – 25

  • Reviewed: 10 August 2025

    9.0
    The location was very convenient for walking to theaters restaurants and park
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 1 night
    • Submitted via mobile

    Great location well stocked kitchen

    Stayed in July 2025

  • Reviewed: 24 July 2025

    10
    Totally recommend!
    • Leisure trip
    • Family with young children
    • Double Room with Park View
    • Stayed 2 nights
    • Submitted via mobile

    Its was very cute and had all thungs that’s you need for two days and nights.

    Stayed in July 2025

  • Reviewed: 17 May 2025

    10
    Sweet place to stay. We would have stayed longer if it had been available.
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night

    Location was easy walking distance to downtown, the natural foods store, theaters, and the park The cottage was roomy and quiet with a good-sized, well-stocked kitchen. Comfy bed and furniture.

    Stayed in May 2025

  • Reviewed: 24 April 2025

    10
    Wonderful in the Heart of Ashland
    • Leisure trip
    • Solo traveller
    • Double Room with Park View
    • Stayed 2 nights

    It was a little difficult to get into and out of the bathtub. Could use a hand support. Could have used a better reading lamp closer to the bed.

    The host, Sugar, was very friendly and upgraded me to a private room with full kitchen. Her communication was exceptional. The bed and linen were top notch. The kitchen bright, clean, and amply outfitted. The living room was comfy; the porch divine. Within walking distance to everything. Quiet.

    Stayed in March 2025

  • Reviewed: 31 March 2025

    10
    The Perfect Cortage!
    • Leisure trip
    • Solo traveller
    • One-Bedroom House
    • Stayed 4 nights
    • Submitted via mobile

    Absolutely fantastic location, quick easy walk to downtown. Super comfortable cottage with everything you'll need. Insanely clean and tidy. Very responsive communication before, during, and after stay-Sugar is wonderful and very helpful. One of the best B&B, AirBnB, VRBO, or other rental I've ever used. Can't wait for a return visit!

    Stayed in March 2025

  • Reviewed: 4 March 2025

    10
    Our host was very sweet and nice. She made sure that we felt at home and that we had everything. Would definitely stay a
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Nothing, it was much better than most places we’ve stayed.

    It was very cozy, clean and homey. It was like we had our own tiny house, very cute.

    Stayed in March 2025

  • Reviewed: 19 February 2025

    10
    We originally booked one night and stayed a total of three when we realized how nice it was
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    There’s nothing about these properties. I don’t like.

    It was beautiful and clean, comfortable and cozy. The host sugar is a doll and wanted to make sure our stay was special amazing place highly recommended.

    Stayed in February 2025

  • Reviewed: 13 February 2025

    10
    Great place to stay.
    • Leisure trip
    • Solo traveller
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    The shower is a bit small but functional.

    It was clean and comfortable and well appointed. The host Sugar is very kind and checked in with me to be sure everything was good.

    Stayed in February 2025

  • Reviewed: 22 October 2024

    10
    We’ll be back.
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Great location! Clean, comfortable. Sugar , the hostess, is exceptionally friendly and accommodating. Well stocked kitchen.

    Stayed in October 2024

  • Reviewed: 19 September 2024

    10
    Exceptional
    • Leisure trip
    • Solo traveller
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    I had a wonderful stay, only wish it could have been longer!

    Stayed in September 2024

  • Reviewed: 23 July 2024

    10
    Terrific stay in Ashland
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 2 nights
    • Submitted via mobile

    Nothing!

    Amazing location and terrific home away from home! Very quiet and relaxing. Comfortable bed and furniture.

    Stayed in June 2024

  • Reviewed: 23 July 2024

    10
    I would recommend this to anyone wanting a great place to stay near downtown Ashland.
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 1 night

    The place was just fantastic. Well appointed, quiet, immaculate, quiet, peaceful. So comfortable.

    Stayed in July 2024

  • Reviewed: 26 June 2024

    10
    Our stay was delightful and we will return soon!
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Great location and the cottage is just charming.

    Stayed in June 2024

  • Reviewed: 12 May 2024

    9.0
    Very nice quiet place, would stay here again!
    • Business trip
    • Solo traveller
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Location is great and the cottage is nicely furnished

    Stayed in May 2024

  • Reviewed: 9 April 2024

    10
    We really enjoyed our time here, everything was good!
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Can’t think of anything I didn’t like.

    It was so comfortable, charming and clean. The kitchen was excellent (BTW, I loved the refrigerator!), and the location was perfect.

    Stayed in April 2024

  • Reviewed: 6 March 2024

    10
    Exceptional
    • Leisure trip
    • Solo traveller
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Beautiful place welcoming clean n comfy and a great location for Ashland Oregon .

    Stayed in March 2024

  • Reviewed: 28 January 2024

    9.0
    Superb
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 1 night

    Seems to be a popular rental, it was unavailable for our return trip. We stay over frequently in Ashland on our trips up and down the West Coast, we will be checking availability of this property first, in future.

    Quiet, private, immediately accessible parking. Full kitchen. This property rents as either a one or two bedroom, with a single large and well equipped bath. Very comfortable front sitting room.

    Stayed in December 2023

  • Reviewed: 18 November 2023

    9.0
    Delightful cottage in the middle of everything. Tons of thoughtful amenities.
    • Leisure trip
    • Group
    • Two-Bedroom House
    • Stayed 2 nights
    • Submitted via mobile

    Nothing

    Location and management

    Stayed in November 2023

  • Reviewed: 18 September 2023

    10
    We enjoyed our short stay at the 2nd St Cottages in Ashland!
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night

    Nothing that I can think of...

    The cottage was adorable and walking distance to the Theaters, restaurants and shops.

    Stayed in September 2023

  • Reviewed: 8 May 2023

    10
    A short notice stay over, it was great!!
    • Leisure trip
    • Couple
    • Double Room with Park View
    • Stayed 1 night
    • Submitted via mobile

    Nothing

    it’s conveniently located.

    Stayed in May 2023

  • Reviewed: 22 September 2024

    8.0
    Nice place to stop and big enough to host gatherings.
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 1 night
    • Submitted via mobile

    $49 cleaning fee, which Bookings does not include in advertised price.

    Allowed for late check in. We were in the Heritage Cottage, which had a nice kitchen, living room and front porch, and has four bedrooms.

    Stayed in September 2024

  • Reviewed: 29 December 2023

    8.0
    Great stay
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 1 night
    • Submitted via mobile

    It was a great place close to everything

    Stayed in December 2023

  • Reviewed: 29 August 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 2 nights

    There are no comments available for this review

    Stayed in August 2025

  • Reviewed: 10 July 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • One-Bedroom House
    • Stayed 2 nights
    • Submitted via mobile

    There are no comments available for this review

    Stayed in July 2025

Showing 1 – 25

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