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.

We enjoyed this stay very much. It was very conveniently located close to Sunday River, which made our skiing plans easy to execute. The hot tub was definitely a plus and the house easily accommodated our multiple adults, kids, and even a couple dogs.

This home is amazing! It was perfect for our group of ten family members that were in the area to celebrate a wedding for the weekend. Our hosts could not have been more accommodating and we were so impressed with their hospitality!! So many nice touches and such a spacious, comfortable home - no detail overlooked. Enjoyed our stay immensely and would definitely return.

Cozy and comfortable place to stay while exploring the area. Close to most anything you’d want to do in Southern Maine.

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 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!

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!

Great 2-level apartment with terrific deck and beautiful view overlooking the river. Quiet and pretty. Owners were very responsive and the kitchen is very well stocked. Nice rustic touches and great running/walking trail along the river, just down the road. WiFi works well. Recommend upgrading the beds as they are small and not very comfortable. Otherwise a great property!

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.

Very beautiful place. Loved the privacy. Jon was very quick to respond to any questions we had. Our pup loved it too. House was clean and had everything we needed. Plan on booking again this summer.

Great place to enjoy the beach and the neighborhood 😃

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

Heathers house was perfect for our group. Plenty of games and thing to keep us busy, and Bridgeton really is a wonderful town. Make sure to check out the local shops on Main Street (especially the antique shop!)