Calderwood Inn

We enjoyed our 2 night stay at the charming Calderwood Inn. This quiet, old house provides comfortable rooms, a large seating area with wine tastings, and a robust, freshly prepared breakfast. It is an easy walk from the Inn to the center of Healdsburg and the Calderwood makes a great base for touring the Sonoma and Napa wine regions.

Lovely old inn with charm and character, but in need of some repairs and a bit of a facelift. It has the land and potential to be more than it currently is: some touch up paint and maybe some cornhole or croquet in the backyard. Complimentary wine and homemade chocolate chip cookies and delicious breakfast. All in all a nice place to stay in walking distance of the square with restaurants and shops.

A lovely inn, with terrific breakfast every morning. Located a nice easy 10-minute walk from the Healdsburg Plaza. Everyone super-friendly. An added bonus is that wine tastings (which they are happy to schedule for you) at any of their ELEVEN related wineries are free!

Great front porch sitting area. Cookies. Wine in living room.

The inn is old and lovely. The staff are friendly, even fun. Wine when you arrive; cookies often.

The staff was extraordinarily friendly and helpful. When we needed assistance with reservations for dinner, they helped get us into restaurants that were fully booked (on Valentine's Day) and we had wonderful dinners. And the inn is also affiliated with 11 tasting rooms with complimentary tastings - a huge deal when so many are so pricy. Breakfast was also lovely and delicious. A wonderful stay and a convenient walk to the beautiful village of Healdsburg.

I loved this inn! It was so relaxing. They made you feel so welcome. The breakfast settings and meals were lovely. The front porch was great for a visit with friends. Easy 10 minute walk into town. I'd come back here in a heartbeat!

Gorgeous B&B with old world charm.... lovely room and the main house was beautiful with no small detail missed. The staff was great and breakfast was terrific. Easy check in and out. Great experience!

Wonderful place to stay as a couple or with a few friends. We enjoyed the nice touches in the room also very comfy bed, comfy sheets, great bay window and plenty of space. When we came back from dinner in there were fresh baked cookies! We sat on the porch with friends and enjoyed a few bottles of wine we picked up close by. Just around the corner from Seghesio’s tasting room. Amazing breakfast served with fresh squeezed OJ and nice strong coffee. Amber is incredibly kind and we really enjoyed speaking with her and getting ideas on where to go next.

One of the best B&B’s we have stayed in. Wonderful food , staff and afternoon wine

Lovely old inn with charm and character, but in need of some repairs and a bit of a facelift. It has the land and potential to be more than it currently is: some touch up paint and maybe some cornhole or croquet in the backyard. Complimentary wine and homemade chocolate chip cookies and delicious breakfast. All in all a nice place to stay in walking distance of the square with restaurants and shops.

Quaint inn within easy walking distance of downtown Healdsburg and easy access to wineries of Dry Creek area. Room was clean and bed was comfy. Bathroom pretty small but adequate. Hot water nice and hot. Variety of food at breakfast could have been better.

We enjoyed our stay. The house needs to be updated. It feels very old. Bathrooms in king size room was so small. It was a great location.

Although the rooms were clean and presentable there were items that need addressing. Screens were damaged, toilet & faucets were leaking, bed was very soft and had dips in it, ac was very loud. We had to change our initial room because there was no air flow and it had a moldy smell. We couldn’t use the ac because it was so loud.

A charming old guesthouse. It was a fairly comfortable place to stay and convenient for walking into the town center and situated right next to the bike path. The guest house has some outdoor seating areas, it would’ve been nice if these were cleaned out for guests to enjoy the outdoor space. Breakfast is served, but there is no communication about any food options or guest dietary requirements. My room on the top floor was comfortable, the bathroom had a lovely clawfoot bath (which needed a better plug to retain the water) but no shower - and sloped ceiling, while quaint, meant no standing up straight in most of the bathroom. Overall, it was safe on a quiet street, comfortable and just right for a couple of nights.

A lovely well furnished B&B with lovely santique furnishings. Gracious hostess . Clean comfortable room . Appreciated the french press to make coffee whenever i want it

Beautiful room with gorgeous bedding and decor. The room was very neat and clean and tidy. The staff was unobtrusive, but very nice and kind when we asked any questions.

The property was charming given its age but it was well maintained and clean. The grounds were really cute. Things ran very efficiently. Parking was ample. Breakfast was great - they did a wonderful job accommodating our dietary needs. I would absolutely stay here again.

We were in the St. Anne’s Suite. Not clean or welcoming at all. Cobwebs on light fixtures, rug stained, very rudimentary furniture. The bed was horrible, on wheels and every time someone moved, it bounced around constantly waking up your partner. The pillows were absolutely horrendous. I asked for ice one day and the innkeeper told me that she has no ice machine and if there is any there might be some in the refrigerator outside because she has to buy it by the bag. My comment is, I think you’re supposed to supply that kind of thing to your guests as part of the hospitality. We do not recommend.

I stayed for three nights in the Matrix room. (When I checked in the paperwork said it was the room I had ‘chosen’ however because I booked on Expedia I was only given a vague description of each type of room - size of bed etc - and the preferred price point). Check in was fine. The woman checking in was kind but seemed eager to leave. Once she left at 330pm there was no one on staff in the house at all until the next morning. This was the case every day. Some pros are that the house is in a quiet neighborhood and the grounds are lovely. It’s also just a 10-15 minute walk to downtown. Cons are: Breakfast was very hit or miss (good the first day and progressively worse each day after). I asked for a quiet room but instead was put in a room at the top of the stairs (again, I didn’t pick my room). It was fine the first day when the inn was basically empty but as the inn filled up it got more noisy. Also the CONSIDERABLE noise coming from the kitchen each morning traveled right up the stairs. The most disappointing part was the room itself. The bed was new and comfortable but as others have noted, my room was shabby. I appreciate that it’s an old inn and that they want to lean into that look, but there were frayed throw pillows, a dilapidated arm chair, cobwebs in the corners, pealing paint on the baseboards and bathroom ceiling and a dingy carpet. The

This place is beautiful and the staff were quite accommodating. Next time, I’d upgrade from ‘standard’ room as I prefer a shower to a tub only.

The Inn is located in an area close to the town square, so it’s convenient to walk to shopping and restaurants. The mattress was a little too soft for my tastes but others may find it to be comfortable. We also didn’t like the sloped ceilings—we were concerned that we’d walk into them

Pros: The location to downtown Healdsburg was great. Walkable to all the great restaurants and shops. Great bathroom and shower in the room. Cons: you only interact with staff at check-in and breakfast. Other than that there is no one around. Our king room was so small there was barely any room for luggage and only one small desk sized chair to sit on. There were no windows other than the entry door so no fresh air in the room and the air conditioner blew directly over the bed. It was fine for 2 days, but next time would book a different room.

A charming old guesthouse. It was a fairly comfortable place to stay and convenient for walking into the town center and situated right next to the bike path. The guest house has some outdoor seating areas, it would’ve been nice if these were cleaned out for guests to enjoy the outdoor space. Breakfast is served, but there is no communication about any food options or guest dietary requirements. My room on the top floor was comfortable, the bathroom had a lovely clawfoot bath (which needed a better plug to retain the water) but no shower - and sloped ceiling, while quaint, meant no standing up straight in most of the bathroom. Overall, it was safe on a quiet street, comfortable and just right for a couple of nights.

My room was in a renovated basement so there was no view and I was under the stairs so it was rather loud. Other than that, I loved everything.

The Inn is a beautiful old building. The decor is charming. My issues have to do with the upstairs bedroom. The weather was very warm for our 3-day stay. The day we arrived, the air conditioning in our room wasn’t functioning. It made for a miserable night’s sleep. The next afternoon the repairman came. The air conditioning was better, but still required a fan at all times. Advice: don’t get an upstairs room in the summer.

Lovely home and convenient to the square. The beds were great and so was breakfast.

I stayed for three nights in the Matrix room. (When I checked in the paperwork said it was the room I had ‘chosen’ however because I booked on Expedia I was only given a vague description of each type of room - size of bed etc - and the preferred price point). Check in was fine. The woman checking in was kind but seemed eager to leave. Once she left at 330pm there was no one on staff in the house at all until the next morning. This was the case every day. Some pros are that the house is in a quiet neighborhood and the grounds are lovely. It’s also just a 10-15 minute walk to downtown. Cons are: Breakfast was very hit or miss (good the first day and progressively worse each day after). I asked for a quiet room but instead was put in a room at the top of the stairs (again, I didn’t pick my room). It was fine the first day when the inn was basically empty but as the inn filled up it got more noisy. Also the CONSIDERABLE noise coming from the kitchen each morning traveled right up the stairs. The most disappointing part was the room itself. The bed was new and comfortable but as others have noted, my room was shabby. I appreciate that it’s an old inn and that they want to lean into that look, but there were frayed throw pillows, a dilapidated arm chair, cobwebs in the corners, pealing paint on the baseboards and bathroom ceiling and a dingy carpet. The

I was really looking forward to our stay at the Calderwood Inn. Unfortunately it did not live up to expectations. I think we were in the worst room at the inn. No hot water came out of the sink. The window a/c unit was loud and did not cool the room. The bathroom had a claw foot tub/shower that was really hard for me to get in and out of. I am in good shape, I'm just short. The pictures listed on Hotels.com and their website did not represent the room I stayed in. I feel like it was a bit of a bait and switch. It was within walking distance to Healdsburg so that was nice and the breakfasts were nice. But since I can't shake feeling of being bamboozled by the how they represented the inn online. It was not worth $300 a night and I wouldn't recommend it to friends.

We stayed 2 nights and the air conditioning just couldn't do the job. In fareness it was in the 80's during the daytime. The room was nice but the bathroom was tiny. The staff was nice and the breakfast was good as well.

We stayed at The Calderwood Inn Valentines week 2025. It is a beautiful, well kept B&B. The people were wonderful and the breakfasts were very tasty. Walking distance to the Healdsburg square and less than 10 minutes to the Dry Creek Valley. We will definitely stay there again!

A lovely inn, with terrific breakfast every morning. Located a nice easy 10-minute walk from the Healdsburg Plaza. Everyone super-friendly. An added bonus is that wine tastings (which they are happy to schedule for you) at any of their ELEVEN related wineries are free!

Lovely historic house, conveniently located close to the square. The staff was very helpful and the breakfast was delicious.

Pros: The location to downtown Healdsburg was great. Walkable to all the great restaurants and shops. Great bathroom and shower in the room. Cons: you only interact with staff at check-in and breakfast. Other than that there is no one around. Our king room was so small there was barely any room for luggage and only one small desk sized chair to sit on. There were no windows other than the entry door so no fresh air in the room and the air conditioner blew directly over the bed. It was fine for 2 days, but next time would book a different room.

The inn is old and lovely. The staff are friendly, even fun. Wine when you arrive; cookies often.

The staff was extraordinarily friendly and helpful. When we needed assistance with reservations for dinner, they helped get us into restaurants that were fully booked (on Valentine's Day) and we had wonderful dinners. And the inn is also affiliated with 11 tasting rooms with complimentary tastings - a huge deal when so many are so pricy. Breakfast was also lovely and delicious. A wonderful stay and a convenient walk to the beautiful village of Healdsburg.

I stayed for three nights in the Matrix room. (When I checked in the paperwork said it was the room I had ‘chosen’ however because I booked on Expedia I was only given a vague description of each type of room - size of bed etc - and the preferred price point). Check in was fine. The woman checking in was kind but seemed eager to leave. Once she left at 330pm there was no one on staff in the house at all until the next morning. This was the case every day. Some pros are that the house is in a quiet neighborhood and the grounds are lovely. It’s also just a 10-15 minute walk to downtown. Cons are: Breakfast was very hit or miss (good the first day and progressively worse each day after). I asked for a quiet room but instead was put in a room at the top of the stairs (again, I didn’t pick my room). It was fine the first day when the inn was basically empty but as the inn filled up it got more noisy. Also the CONSIDERABLE noise coming from the kitchen each morning traveled right up the stairs. The most disappointing part was the room itself. The bed was new and comfortable but as others have noted, my room was shabby. I appreciate that it’s an old inn and that they want to lean into that look, but there were frayed throw pillows, a dilapidated arm chair, cobwebs in the corners, pealing paint on the baseboards and bathroom ceiling and a dingy carpet. The

We loved the location and friendly and helpful staff. Lovely breakfast and great to be able to chat to other guests

Breakfast was delicious . Staff very supportive and clear in the instructions to check in late. Super recommendable.

Very cute B&B. Staff is friendly and it’s easy to walk to the town of healdsburg

We stayed at The Calderwood Inn Valentines week 2025. It is a beautiful, well kept B&B. The people were wonderful and the breakfasts were very tasty. Walking distance to the Healdsburg square and less than 10 minutes to the Dry Creek Valley. We will definitely stay there again!

We enjoyed our 2 night stay at the charming Calderwood Inn. This quiet, old house provides comfortable rooms, a large seating area with wine tastings, and a robust, freshly prepared breakfast. It is an easy walk from the Inn to the center of Healdsburg and the Calderwood makes a great base for touring the Sonoma and Napa wine regions.

Quaint inn within easy walking distance of downtown Healdsburg and easy access to wineries of Dry Creek area. Room was clean and bed was comfy. Bathroom pretty small but adequate. Hot water nice and hot. Variety of food at breakfast could have been better.

A lovely inn, with terrific breakfast every morning. Located a nice easy 10-minute walk from the Healdsburg Plaza. Everyone super-friendly. An added bonus is that wine tastings (which they are happy to schedule for you) at any of their ELEVEN related wineries are free!

Very good location and quite

Nice rooms, good breakfast, easy to walk to shopping area and tasting rooms. Would definitely go back.

Pros: The location to downtown Healdsburg was great. Walkable to all the great restaurants and shops. Great bathroom and shower in the room. Cons: you only interact with staff at check-in and breakfast. Other than that there is no one around. Our king room was so small there was barely any room for luggage and only one small desk sized chair to sit on. There were no windows other than the entry door so no fresh air in the room and the air conditioner blew directly over the bed. It was fine for 2 days, but next time would book a different room.

The place is very nice, the location is great and I would stay there again.

I stayed for three nights in the Matrix room. (When I checked in the paperwork said it was the room I had ‘chosen’ however because I booked on Expedia I was only given a vague description of each type of room - size of bed etc - and the preferred price point). Check in was fine. The woman checking in was kind but seemed eager to leave. Once she left at 330pm there was no one on staff in the house at all until the next morning. This was the case every day. Some pros are that the house is in a quiet neighborhood and the grounds are lovely. It’s also just a 10-15 minute walk to downtown. Cons are: Breakfast was very hit or miss (good the first day and progressively worse each day after). I asked for a quiet room but instead was put in a room at the top of the stairs (again, I didn’t pick my room). It was fine the first day when the inn was basically empty but as the inn filled up it got more noisy. Also the CONSIDERABLE noise coming from the kitchen each morning traveled right up the stairs. The most disappointing part was the room itself. The bed was new and comfortable but as others have noted, my room was shabby. I appreciate that it’s an old inn and that they want to lean into that look, but there were frayed throw pillows, a dilapidated arm chair, cobwebs in the corners, pealing paint on the baseboards and bathroom ceiling and a dingy carpet. The

Very cute B&B. Staff is friendly and it’s easy to walk to the town of healdsburg

We enjoyed our 2 night stay at the charming Calderwood Inn. This quiet, old house provides comfortable rooms, a large seating area with wine tastings, and a robust, freshly prepared breakfast. It is an easy walk from the Inn to the center of Healdsburg and the Calderwood makes a great base for touring the Sonoma and Napa wine regions.

Built in 1908 it was filled with "old-fashioned" charm. The breakfasts were amazing - quite substantial considering we usually have a piece of toast and some fruit. Yummy for sure.

Quaint inn within easy walking distance of downtown Healdsburg and easy access to wineries of Dry Creek area. Room was clean and bed was comfy. Bathroom pretty small but adequate. Hot water nice and hot. Variety of food at breakfast could have been better.

We had a wonderful stay. The only issue was that the fact that one of us is lactose-intolerant did not get communicated to the kitchen staff the first day, but when they did know they were very accommodating.

Lovely historic house, conveniently located close to the square. The staff was very helpful and the breakfast was delicious.

Lovely grounds and rooms. Delicious breakfast.

The property was charming given its age but it was well maintained and clean. The grounds were really cute. Things ran very efficiently. Parking was ample. Breakfast was great - they did a wonderful job accommodating our dietary needs. I would absolutely stay here again.

Breakfast was delicious . Staff very supportive and clear in the instructions to check in late. Super recommendable.

Gorgeous B&B with old world charm.... lovely room and the main house was beautiful with no small detail missed. The staff was great and breakfast was terrific. Easy check in and out. Great experience!

My husband and I booked a weekend here and it was for the most part lovely. We especially loved the beautiful gardens, common areas, especially the massive, yet cozy front porch. It is an old house and our bathrooms reflected this--especially struggled with the clingy, stiff-plastic curtain around the cast iron tub for showering. Staff were attentive, with lovely extras such as wine served in the afternoons with a charcuterie board or cookies. The breakfasts were not quite up to what I would expect for a place this wonderful.