Rooms & Rates

Rich History, Modern Luxury

The Inn has 20 beautiful guest rooms each filled with modern amenities and decorated to keep with the tradition of the building. If you’re looking for accommodations with a modern flair, our Barn Building offers contemporary comfort. Guests looking for a more historic experience will enjoy the historic mansion, with its authentically preserved sleeping quarters with Victorian furnishings and pressed-tin ceilings.


Historic Building Guest Rooms

$179 – $250

Immerse yourself in Victorian elegance when you stay in any of these king-sized suites. Guestroom floors boast a variety of hardwoods, cut in the surrounding forest and milled in the Winter’s own mill. Distinctive, colonial furnishings decorating each room will transport guests back to a simpler time.

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Barn Building Guest Rooms

$149 – $180

Guest rooms in our Barn Building combine country comfort, value and modern amenities. Accented with historic traces, each room boasts luxurious bedding and fine furniture. Enjoy the view from these rooms as you gaze out over the Carrabassett River and take in the breathtaking views of the lush, rolling New England countryside.

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“We stayed at this quaint Inn for three nights this past week. The rooms in the Main House are large, clean, comfortable and decorated in period antiques. The food and drinks at the Inn are simply put “amazing”, with a variety of foods to please the most demanding appetites. The staff was exemplary! In order of appearance, Cate, Mason, Kristin and John couldn’t have been more welcoming, attentive and pleasant to converse with. We really felt at home here. We were fortunate enough to meet several of the local residences of Kingfield, ME who also made us feel right at home. The Inn on Winter’s Hill will definitely be a repeat for us next spring as we came up to explore the area on our motorcycles and found this to be a hidden gem.
Thank you to all of you for making our stay a great one. Until next time….”
September 16, 2018
Barbara & David Crockett
Middleboro, MA



Rates are subject to change without notice.

  • Rates are quoted per room, per day and vary according to whether it is single or double occupancy.
  • The Inn is not a Bed & Breakfast.  Full breakfast is available in the dining room at a charge of $12. per person.  If you wish to have a rate that includes breakfast, we can do that.
  • Additional fee of $20 per person applies for ages 13 years & older sharing a room for triple and quad occupancy in the Dbl/Dbl rooms. (Children 12 years and younger no extra charge.)
  • Most weekends require a two night stay and some holiday periods require a 3 night minimum.
  • 9% Maine state sales tax will be added to your bill.
  • Check-in time begins at 3PM. Check out is 11AM.  If you have a different requirement, let us know and we will work with you whenever possible.

Ask our Reservationist about a personalized In-Room amenity for an even more memorable stay, whether it is a floral arrangement, spa products, chocolates, or romantic items.  With enough notice we can equip your room with almost anything.


To confirm a reservation, The Inn requires the full deposit of your stay.


Because of our small size, cancellations affect us significantly.
A last-minute cancellation gives us little chance of booking the cancelled room due to our remote location, thus The Inn has the following 14 day cancellation policy:
Any cancellations outside of 14 days of your stay are subject to a $20 administrative fee.
Cancellations within 14 days but outside of 48 hours are subject to 50% of your deposit, or 1 night’s stay, whichever is greater.
Cancellations within 48 hours are subject to a full forfeit of the deposit.
Should it be necessary for you to depart earlier than your confirmed departure date, you will be responsible for your entire stay as originally booked.

Pets Welcome

The Inn understands how wonderful it is to share an outdoor vacation with your canine companion. We expect our pet guests to be clean, quiet and well-behaved.  If you cannot guarantee these three things, don’t bring your pet. We  invite you to bring your pet and stay with us in one of our deluxe accommodations with the following guidelines:

  • When outside of their guest room, pets must be on a leash and owners must clean up after them. Pets are permitted on designated cross-country ski trails.
  • We make a $20. per night per pet charge to cover extra cleaning at checkout. Pet Walkers are available with 3 days advance notice. Sitters will exercise your pet at a rate of $12 per walk.
  • We reserve the right to refuse daily housekeeping service to rooms in which a pet is left loose in the room.
  • The Inn reserves the right to charge guests if after departure there is property damage, “accidents,” noise complaints, or disregard for our other guests. Should your pet seriously damage any of the Inn’s property, you will be charged full replacement value. Chronic disturbance issues may result in our requiring you to take your pet(s) to a local kennel.
  • Out of respect for non-pet-oriented guests, pets are not allowed in any of the guest rooms of the Historic building or the Dining Room, Living Room bar, or Historic building Lobby Areas.