Family-friendly holiday rentals in Woolwich

Lori’s is exactly what we need while visiting family over a holiday. She is very gracious to host us over Thanksgiving as the last occupants of the year. Even during a snow storm, her place is cosy and beautiful. This is our second year coming, and we love it every time. We would recommend it for those looking for a charming getaway from busy life. Thanks Lori!

We enjoyed our stay and had plenty of room. I loved the layout and the ability for our group to be able to interact together and the view of the ocean was great.

The hot tub and scenery are the highlights of this rental. The king size bed is not common and it was comfortable compared to other AirBnBs or VRBOs I've stayed in. Definitely plan to come back and enjoy another time of the year

We love staying at the Brownie. It’s a great home for any active family that appreciates a quiet surrounding. Great home and so close to SR. It can’t be beat.

Odena by the Sea is amazing. Great location and the home had everything you could need and even more! Wish we could have stayed longer but look forward to returning in the warmer months!! Jason was very attentive and responsive with any and all questions/concerns!

Had a great stay Deb's place in Andover. Plenty of space for our group of 3. The hot tub was perfect after two days of skiing and hiking. We also enjoyed getting takeout from Mills Market. Deb is a very friendly host and we had a great stay.

Wendy is absolutely amazing, she’s the sweetest I absolutely loved her and her rental i couldn’t have chosen a better place I’ll absolutely be visiting again

This was our second time staying here, my family and I love the tranquility of this little piece of heaven. Christopher’s home was beautiful, clean and well maintained.

Marcia’s place is very cozy and charming. Plenty of space and a comfortable accommodation. Would stay here again.

amazing stay! hosts were awesome and place was exactly as described. would stay here again!

Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

This was the fourth time I have come up to Jayne's to get away from it all. No wifi or cable is what I like best. If you are looking for a peaceful digital detox this place is perfect. I hope to come back in the summer sometime. I will definitely be back next February.

Cammie’s listing wad everything and more. My entire family was able to stay all together with the comfort of a warm welcoming house. Very spacious and the table in the great room was absolutely perfect to have a meal with everyone. My favorite part of this house was there there was only 1 TV in the whole house and many games and puzzles available to enjoy being with the family and not zoned to tv. What a great experience.

We loved our stay at Katie's house in Portland. It was very comfortable, clean and nicely decorated. We would love to stay again soon!

It was the perfect location for a group of 6. Plenty of space and comfortable common area with a nice large dining table. Wonderful location and very walkable. Host was proactive with communication and very responsive. Highly recommend! Thanks for a wonderful stay and would absolutely return!

My family and I loved staying at Tanja's home, which is saying something as my family members can be quite particular! Tanja was extremely communicative and amenable to my requests for check-in and check-out. Her place is impeccable and all of us LOVED her collection of artwork and eclectic curios throughout each space--we could come back again and probably find more things we didn't notice after staying for over a week! Tanja had thought of everything, putting a lot of effort into the home's details so that I was left wanting for nothing. My family also loved listening to records throughout the day and evening. A great place for a long-term stay: I found myself saying that I was going back "home" after a long day out. Thanks so much, Tanja! We'd love to come back the next time we're in the area.

We loved the old building with so much charm and character. The place was clean and well furnished. The surrounding is beautiful and location is convenient. Plenty of beds, but remember, they are all narrow twins. No queen bed in any room. More of a dorm set up in each room. Kitchen has enough utensils, plates and silverware for 20. But carry your own spices and condiments- including oil, salt and sugar. This house is part of Poland Spring Inns and Resorts.

Great home for our large family gathering. Great location near Sunday River skiing, Downtown and snowmobile trails right outside the door. We had a great time and will be back.

Amazing quiet little getaway even in the cold windy winter the hot tub made for fantastic nights to be able to be outside and look at the stars, will definitely book again

No frills but perfect for what we needed. Easy ski in and ski out. Kitchen is a bit tight and very little cooking stuff but otherwise comfortable and great for a ski weekend

Great place to rent with easy ski in and out from the mountain!

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

We found the home clean and welcoming. There was plenty of room for all of us and we enjoyed the back deck very much. The kitchen was well equipped and although we did not do any cooking, if we had, everything was there for us. We really liked how private the home was. Had the weather been warmer we definitely would have checked out the pool. It is also very close to Thomaston, Rockland and Owls Head. So much to do in this area. We would recommend this home to anyone who wants a quiet retreat in Maine that is close to the coast.