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Winding Way Bed and Breakfast

39 Union Street , Rockland, ME 04841 USA (Show map)
8 Reviews
$155 - $175
per night

Check Dates


Winding Way B&B is in a circa 1855 house in the arts and downtown section of Rockland Maine. The house has been renovated leaving the period architectural details such as tin ceilings, woodwork and the original staircase. Our bed and breakfast is on the second floor and our art gallery is on the first floor. Rockland is a wonderful area for bicycling and as avid cyclists we know all of the best routes. We will provide you with maps and make sure you get a bike if you do not bring your own. 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 with many potted plants. We serve a continental plus breakfast with local fruit, homemade scones and bread and quiche very often with lobster in it. The house formally included an ice cream parlor and we serve ice cream to our guests. There is free WIFI, onsite parking and a gift shop that carries prints and note cards of our artist's work. You may rent the entire B&B which gives your group exclusive use of two bedrooms with ensuite bathrooms, use of the sitting room with full sized bed, sunporch, guest kitchen areas and the gated enclosed patio. A port a crib and toddler cot are available and included, This is the only rental plan that children are accepted at the B&B. Checkin time is 2:30PM to 4:30 PM but definitely by 6 PM. Since we do not live on site we like to know when you are coming so we can welcome you.

Rooms & Rates


THE SARAH THURLOW ROOM is the larger of our two rooms. It is on the front of the house and looks out on Union Street and The Farnworth Museum's Wyeth Center and Research Center, both of which are original buildings of the city of Rockland. It has 2 comfortable chairs for relaxing, a skylight in the shower and a large closet.

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

Nightly Rate: $175/$175


THE EDWARD THURLOW ROOM is our room on the back of the house. It is only slightly smaller than our other room and it s a very comfortable room with a mariner theme. The windows look out the back of a children's art gallery and at flower baskets on our small stone patio. The room has a queen bed, 2 chairs and a built in closet to hold all of your belongings. The ensuite bathroom has a new tiled shower.

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

Nightly Rate: $155/$155

Whole House rental

You may rent the entire house which gives your group exclusive use of two bedrooms with ensuite bathrooms, use of the sitting room, sunporch, guest kitchen areas and the gated enclosed patio. There is a sleeper sofa in the sitting room. A port a crib and toddler cot are available and included in the nightly rate. High chair and toddler table also available . Maximum 4 adults and 3 children. The rate is $ 320.00 per night. This is the only rental plan that children are accepted at the B&B.

  • Maximum Capacity: 4
  • Bathroom Private Bath

Check Dates



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  • Guest room4.5
  • Services4.5
  • Value4.0
  • Cleanliness4.9
  • Dining3.8

Score Breakdown based on
8 Reviews

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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.

Sept 3-5

5 on September 09, 2013

The B and B is meticulous and brand new, the decor is lovely, the menu delicious, and the owners are so wonderful. We were absolutely thrilled with our visit and hope to return soon

Lovely Place

4.2 on August 17, 2013

Winding Way is a cute, clean, and friendly place to stay, and the location is great. The innkeeper does not live onsite, so you serve yourself breakfast downstairs. (Our breakfast was pretty good.)

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Location Type

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


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

Directions to property:

Follow 295 North to exit #28 ( coastal route route 1). Follow route all the way to route 90 outside of Camden and Rockport. Turn left onto route 90 as above.

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, summer music, lobster and boat festivals, bicycling, Performing Theater, Religious Services, Ski area, Vineyard, Winery, 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

Inn Details

Establishment type

Bed and Breakfast, Other

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

Check Dates


  • Check In:: 2:30 PM- 4:30
  • Check Out:: 11 AM
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Suitable For Children: If both of our rooms rented by the same group infants ok
  • Guest Pets Allowed: No

Terms and Conditions

  • 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.

Check Dates



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.

Details Diamond Collection

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

Property highlights

Get a free $20 gift card with every gift card purchase of $100