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Winding Way Bed and Breakfast

39 Union Street , Rockland, ME 04841 USA (Show map)
15 Reviews
$165 - $165
per night

Check Dates


WINDING WAY IS NOW CLOSED. IT IS CURRENTLY FOR SALE. WE FEEL IT WOULD MAKE AN EXCELLENT SITE FOR AN UPSCALE RESTAURANT, other commercial venture or a beautiful downtown private residence For information on previewing the house please call Ed Glover at Megunticook Real Estate, Camden Maine. @ 207- 504-7606 or reach him by email at edwglover@gmail We want to say thank you to all of our past guests. It was a pleasure to have you at the B&B. Anne and Jon McMath The house has been renovated leaving the period architectural details such as tin ceilings, woodwork and the original staircase . We have two sunny rooms both decorated in lovely seaside colors with new queen beds. Each has it's own ensuite bathroom with shower with sea glass accents. Rooms have comfortable chairs and footstools to relax after day of exploring lighthouses, beaches, islands, shops, art galleries and eating lobster whenever you can ! There are guest sitting areas on second floor, on the sunny enclosed front porch and outside on patio .



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  • Guest room4.6
  • Service4.6
  • Value4.2
  • Cleanliness4.9
  • Dining4.0

Score Breakdown based on
15 Reviews

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Perfect stay

4.8 on November 05, 2014

With just two guest rooms, this is a perfect small B&B with excellent personal attention, local knowledge and enthusiasm from Anne. Anne's home-made breakfast - different each day - is superb! Really good location right in central Rockland, a short walk from galleries, restaurants and stores.

Cozy and friendly.

4.6 on October 25, 2014

Even though we were on our own for breakfast, Anne made a delicious egg dish we could heat ourselves, fresh fruit and muffins or bread, juice and coffee. Our room was lovely with a modern bathroom. She's thought of everything from reading material to a late night ice cream treat.

arts and lodging

3.2 on October 15, 2014

This is a great place to spend a night or two. My bed was very comfortable, and the room was quiet and tastefully decorated. This place is somewhat unusual in that it offers a "self-service' breakfast, but it was of high quality. I would definitely recommend this place. It's right near the Farnsworth Museum, lots of art galleries, and many good restaurants. I hope to return there sometime.

Fantastic B and B!

5 on October 08, 2014

First time staying in a B and B in the US and this one will be hard to top. Anne, the proprietor, was so welcoming and accommodating. The room was comfortable and clean and the breakfast was incredibly delicious. She had cookies and lemonade waiting for us on arrival, ice cream at night and chocolates on the bedside tables. What a warm and gracious host! We would definitely recommend this and also stay here again if we are ever in the area.

1 night stay

4.8 on August 29, 2014

great deal

Our stay at Winding Way.

4.8 on August 24, 2014

We only ate breakfast at Winding Way. It was fine. We did not require room service so we cannot rate that.

Outstanding is the word for Winding Way B & B

5 on June 18, 2014

When we came back again this year we felt like we came back home. This is a great place with awesome owners. Their attention to detail is amazing. You do not want to leave because you get spoiled! Phil and Vicky

Winding Way - A Great Find

4.8 on November 12, 2013

This is a charming B&B - and water color art studio - located just a block from the Rockland waterfront and Main Street shops and restaurants. It offers only two rooms meaning those traveling with another couple (as we did), or a family, can have the entire house at their disposal. The rooms are very pleasant and very well kept. The most interesting aspect is that the owner is non-resident; however, that doesn't mean that guest aren't cared for exceptionally well. The kitchen/dining area is spotless, the fridge is well stocked, and breakfast - although a do it yourself meal - was excellent. Fresh scones, juices, fruits, quiches, coffee and tea were first rate. There are only two interesting aspects to consider. First is that arrivals must be coordinated with the owner so someone will be available to provide initial access. We were remiss in doing that, although it took only a phone call to rectify the oversight. Second, there is only one rather small parking area reserved for the B&B and it did not appear that two large vehicles could be accommodated. Of the B&Bs we've sampled in Rockland, the Winding Way is by far the finest. Ah yes, it's also very close to the Farnsworth Museum complex which should be a "must see" while visiting Rockland.

Innkeeper Response
We are so pleased you had a good time at Winding Way. I will make sure that our site reflects the need to call us with your arrival time. We try to call each guest the day before but sometimes the number given is incorrect. We have complimentary parking for larger vehicles behind The Wyeth Museum which is directly across the street from us. Our website and welcome letter includes this information. Thanks fro bringing it to our attention.

Artistic gallery, plastic dishes

3.6 on October 18, 2013

Wonderful idea - an art gallery that is also a B&B. Guests can look at the art at night, as the gallery stays open. VERY friendly owner, very eager to please. Very clean and in a great location - right across from the Farnsworth Art Museum and in the heart of a city full of galleries and shops. Two drawbacks: heavy breakfast put into red plastic microwave containers for guests to heat up - unappetizing. Also you can hear guests in the other room laughing, talking and yes (the real problem) snoring all night long.

Innkeeper Response
We are happy that you enjoyed the art gallery and location of our bed and breakfast. Our breakfast does need to be reheated in our red pottery dishes as we do not live on site. The only plastic we use at the B&B is in bathrooms because of the tile floors. We most often serve fresh fruit but I believe this guest was served baked apples to be reheated as it was a fall visit. Sorry they didn't look good to you and we apologize. Guests love our individual quiches but they have to be reheated in the microwave. We let all guests know about quiet hours in the B&B but we will reemphasize that to guests. I guess occasionally we will have a snorer but hopefully only a few. We do have sound machines in our rooms and I will change our welcome letter to reflect that if you are a snorer please use the sound machine in your room at night. Thanks for writing the review and we hope you will return to winding way.

Nice stay, with some limitations

3.4 on October 01, 2013

Beautiful place, nice rooms. A bit noisy as our room was overlooking the street, with steady traffic starting early in the morning. Breakfast was just ok -

Innkeeper Response
We are happy you enjoyed our rooms. We are currently having some sound proof windows installed . Thanks for the review.

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Rooms & Rates

The Edward Thurlow Room

This room with a queen bed is on the north side of the house. The windows look out at the stone patio. The room is decorated in a mariner theme with linens in soft blues,yellows and greens. The built in closet under the eaves can hold all of your clothing and shoes. The room has two comfortable chairs with footstool for relaxing. The ensuite bath has a new tiled shower with sea glass accents. A portable air conditioner is available for the occassional warm Maine night. There are shades should you want to sleep in.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $165 - $165

Nightly Rate: $165 - $165

​The Sarah Thurlow Room

This room with queen bed is on the front of the house and looks out at The Farnsworth Research Building and The Wyeth Center. It is decorated in white and light blue with a shell theme. The ensuite bath has a new tiled shower with sea glass accents and a skylight. There are two comfortable chairs for reading and relaxing and ample closet space. There are blackout shades if you want to sleep late. A portable A/C is available for the very occasional warm Maine night.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $165 - $165

Nightly Rate: $165 - $165

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Location Type

Walk to town and restaurants, Walk to beautiful working harbor, Near Bus and ferry terminal, Near Museums, Near Rennovated local theater, Arts and downtown district, Airport, Downtown, Mountains, Small town, Village


Portland, ME (PWM-Intl. Jet Port) 90 miles

Directions to property:

Coming from the south- At the intersection of Route 1 and route 90 ( sign says to Camden, Rockport), turn left onto route 90 and follow it to the intersection of route 17. Turn right onto route 17 and follow it to route 1( McDonald's on the left). Turn R onto route 1, which turns into a one way street which is Union Street. Go past the court house on the right. Winding Way- 39 Union Street- is on the left just past the Wyeth Center. There are two parking spots just to the right of the house ;Coming from the north- follow route one to intersection of route on and 17 and route one. Route one south becomes Union Street. Go past the court house on the right. Winding Way is on the just past the Wyeth Center. There are two parking spots just to the right of the house.

Area Attractions

Antique Shopping, Art Galleries, Beach, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Ocean, six light houses nearby, harbor with sailing cruises, Farnsworth Museum and Wyeth Center very near, harbor boardwalk, bicycling, summer music, lobster and boat festivals, Performing Theater, Religious Services, Ski area, Vineyard, Winery

Inn Details

Establishment type

Other, Bed and Breakfast

On-site amenities

Washer/dryer , bike rental and parking, art gallery and gift shop on site, Complimentary Ice cream for guests, lovely sunroom with rocking chairs, Self serve breakfast with homemade scones & quiche, child sized table and chairs

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, Board games, Coffee/Tea facilities, Computer, In-room internet, Desk, Fridge, Hairdryer, Internet Service, Ironing Board, Library, Microwave, Private entrance, Radio, Telephone, Wi-Fi

On-site activities

Bicycle rental, Bicycle riding trails, Bicycles, Bird watching, Boating, Cross-country ski trails, Downhill Skiing, Fishing, Golfing, Hiking trails, Kayaking, Sailing, Shopping, Sight-seeing, Snow shoe rental, Snow shoe trails, Swimming

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  • Check In:: 2:30 PM- 4:30
  • Check Out:: 11 AM
  • Open All Year Round: Yes
  • Smoking Allowed: No house and grounds
  • Drinking Allowed: Yes
  • Alcohol Provided No
  • Suitable For Children: Yes If both of our rooms rented by the same group or family.
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • Disabled Access No

Terms and Conditions

  • Accepted payments AMEX, VISA, Discover, Mastercard, Personal checks, Travelers checks, Cash
  • Deposit Amount Required: 50 % or 1 night whichever is less is required to hold the room. Balance is due at check-in.
  • Cancellations: If cancelled within 14 days the deposit will be returned minus a 25$ service charge. After two weeks the deposit will be forfeited unless we can rent the room and then only a 25$ service charge is required. If cancellation is within 48 hours the entire charge will be taken unless the room can be rented. In that case a voucher will be issued for a visit in the next 365 days.



Anne McMath

Languages spoken

un peu francais, English

About the innkeepers

Anne is a watercolor artist and one of the four current artists showing in our art gallery- Winding Way Watercolors. Both Anne and Jon are avid bicyclists and can show you all of the great routes.

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Continental Plus

  • Time Served: when you are ready until 11 AM
  • Serving Location: Breakfast Room

Special meal options

Low fat , Restrictive , Vegetarian

Signature Dish

Several varieties are served.


39 Union Street , Rockland, ME 04841 USA (Show map)

Property highlights

Free $20 gift card!