Winding Way Bed and Breakfast & Art Gallery

39 Union Street, Rockland, Maine 04841
Innkeeper(s): Anne and Jon McMath, owners & innkeepers; Terry and Patti Lawry, Assistant Innkeepers

The Sarah Thurlow Room

$165.00 / $165.00 night

The Sarah Thurlow Room sits at the front of the house.

  • Queen bed
  • White, light blue and shell themed
  • Private ensuite bathroom
  • Sitting area
  • Ample closet space
  • Blackout shades
  •  A/C provided

The Edward Thurlow Room

$165.00 / $165.00 night

Located on the North side of the house.

  • Queen bed
  • Decorated in a mariner theme
  • Built in closet
  • Sitting area
  • Ensuite bathroom
  •  Portable A/C is provided
DVD Player
Eco-Friendly Inns
Historic Inns

Rent the Whole House

$300.00 / $300.00 night

Rent the whole house!

  • Both Edward and Sarah Thurlow rooms
  • Sitting room
  • Sunporch
  • Outside fenced patio
  • pack n'play, toddler cot included; high chair in kitchen
  • Small convention oven

The whole house can accomodate up to 4 adults and 3 children.

320 $  per night . Call for this plan

Historic Inns
Kid Friendly
  • Guest Information

    Continental plus breakfast is included with room rates.

    Arrivals and Departures

    • Check-in 1:00pm - 4:00pm
    • Check-out 11:00am
    • Arrangements can be made for other times if needed. Please call us
    • Luggage storage for later departures is available.


    • Children are welcome if the whole house is rented by the same group.
    • Pack n' play and toddler cot are available.
    • A toddler table is available in the sitting room.
    • High chair is also available.
    • A stair gate is available for safety.


    Pets cannot be accomodated, however there is a kennel nearby with a swimming pool.


    • 50% of total reservation or payment for one night is required to reserve room. (Whichever is greater.)
    • Cancellations must be made 14 days prior to your reservation dates for a full refund, less a $25 booking fee. Any day after, the depost will be forfeited.
    • Cancellations made within 48 hours of arrival are subject to pay the entire reservation charge.
    • If your room is re-booked, you can receive a voucher to stay at Winding Way Bed and Breakfast, valid for one year.
    • Visa, MasterCard and American Express are accepted.