Family-friendly vacation 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!

Meghan's home was a perfect place to stay for my sister's Bachelorette weekend! The home is located in a quiet community with views of the river and bay, and it was conveniently located with just a short drive into the heart of Portland. We found our stay extremely comfortable, especially on such a cold and dreary April weekend. Meghan had the hottub ready for us with matching robes for all which was a fun surprise. Check in and check out were a breeze. We even took a breakfast recommendation from the guest book (Forage Market, yum!), a tasty experience indeed. Thanks again, Meghan!

We had the most amazing stay at Madawaska! Amazing views from the bedroom and hot tub in a beautiful, peaceful, and private location overlooking the water. And such a wonderful design of the cabin. We will definitely be back!

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.

This house has a beautiful location super close to the beach and a close walk to restaurants and activities. It has great views and plenty of room for a large group! Check in was super easy and they greeted us and went through everything so clearly that we knew where everything was and how to use it all - which was very helpful with such a big place with so many amenities. The hosts were communicative and helpful leading up to our stay and again with check out. The house itself is stunning with everything stocked for your stay. The only thing to be aware of is that there is a train that runs close by so definitely bring your sound machine. Would definitely rent this place again!

I was happy to return to stay at Deb's, this time around in the studio loft. It was very spacious and comfortable and included anything that you might want or need. It was a perfect spot for me to rest while watching ski races at Black Mountain for the weekend. Thanks for being a wonderful host once again, Deb!

Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

Paul's house was wonderful! It smelled so fresh when we arrived and was very clean. The house was more spacious than i expected. It was just us two of but could absolutely fit another couple and a few kids with plenty of privacy. We really enjoyed fires in the wood stove with firewood provided. The soaks in the hot tub were amazing! The beach towels were greatly appreciated for wrapping up in to hurry in from the cold! We had fun grilling in the snow and found everything we needed in the kitchen. We felt right at home. Our dog had a blast playing in the big backyard too! Paul has great communication and was very fast to respond. Paul's vacation home is perfect place to relax and unwind! Thank you for sharing your beautiful Maine getaway Paul!

Great communication, easy to work with, great place, great location. Exactly how described.

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

Great cabin for my family of 4 and our dog for a quick ski trip. I have 2 boys aged 14 and 11 who loved the loft area. We stayed to ski at Saddleback for 2 days, so was in the cabin l for just breakfast and then evening. Is described accurately in listing. Enjoyed our time!

We had a wonderful stay at this Maine house--Barb, the property manager was incredibly responsive, helped with a heating issue while we were there and had the repairs done same day--The house was well equipped with everything you need for a family getaway at the beach! puzzles and games galore, kitchen was fully stocked with everything needed for family meals (including lobster cooking essentials--bibs, crackers, steam pots) Great little fire pit out front which we enjoyed, and fenced in back yard area so pets or kids can be safely contained :) Linens, towels, all clean and provided--truly a wonderful home away from home, perfect for our family trip to the beach!

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!

The place was nice and spacious. Good layout. Great kitchen. Kathy was super responsive and gave good local recommendations.

Great location and great host! Super interesting and thoughtful artwork, wonderfully close to our destination (daughter visiting Bates college to consider attending there), and a super friendly and helpful host. Can't be beat!

I have stayed at Anne’s place many times. Anne and her husband are always very nice and friendly. The apartment is spotless, comfortable and you can’t beat the location, just up the hill from charming Falmouth Town Landing and beach and an easy drive to downtown Portland.

Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!

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.

Was a very nice peaceful getaway the home was spotless and had everything we needed plus extra great place to disconnect

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

A good ski in ski out location. Perfect for us. Thank you.

We absolutely loved our visit to Appledore Cottage! It was quaint and perfectly relaxing. The screened in porch was the best place to just sit…very quiet and peaceful!

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