Family-friendly holiday rentals in Woolwich

A beautiful rustic cabin in an amazing spot. Lori is a great host and is always near in her farmhouse to communicate and get you what you need. Appleton is not far from Camden / Rockland but has that rustic getaway feel. The option of adding a wonderful soak in the hot tub, wood fired sauna, massage and breakfast are available as well. I’ll be back next year! Thank you for everything, Lori!

The house was perfect for our group of 12. It was spacious and well-cared for. While not located in downtown Portland, it was just minutes away by car. There was ample parking in the driveway and on the street. Meghan was a very responsive and flexible host. We had a great time.

David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

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.

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!

This beautiful venue was worth every penny. Chris greeted us and made us feel right at home, even pointing out opportunities for viewing local wildlife! Our party of 10 (ages ranging from 14 to 74) never felt crowded, a floor for every family! The kids even played "hide & seek" in the house. We made memories that will last a lifetime. Try as we may, we can't think of one thing we would have changed about our stay. Thank you Chris, Jason and family for sharing this beautiful home!

Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.

We had a very relaxing vacation. Verona Island is convenient for day trips to a number of attractions like Acadia, Camden and even Monhegan Island. Even when the weather was bad there was plenty of table space for puzzling, Bananagrams and Scrabble. The house was comfortable with views of the Penobscot River.

This place is as-described and then some. Private, secluded, and peaceful. You have the water to yourself and virtually no noise around you (other than what your group makes!). Wallace’s has pretty much anything you need grocery-wise and good breakfast and lunch sandwiches. Pizza is good, too. The house is stocked with all the basic necessities and consumables, and then some. Probably the best-stocked ABNB I’ve stayed at (all the way down to q-tips in the bathroom). Friendship is far off of the tourist path, but not too far to go see things. The house was a perfect fit for our group of six adults and four teens. They never ran out of things to do (including fast WiFi, unfortunately—dad speaking there, not a knock against the house). The owner was very responsive to messaging. I can’t recommend this place enough.

We had a wonderful week on the lake fishing and played some golf nearby at Natanis GC. The water was a little high so not all the sections of dock were in, but we were able to manage two 20' bass boats . I thing we all agreed that we loved the campy feel of the place and will most likely rent there again.

The Captain Fuller House is a beautiful place to stay - gorgeous location, bright and airy rooms and one of the best cottage kitchens of any place I’ve stayed at locally. We hope to come again!

Our stay at Margaret's home was very relaxing and comfortable. Pristine bathroom, kitchen and bedding. The lake view was so much more than we anticipated. It was serene, peaceful, and breathtaking. She went out of her way to answer questions for us about the area, and we left feeling like we just gained a new friend. Jeff and Donna

I cannot say enough positive things about Emily and Matt’s beautiful cottage. It overlooks a blueberry field with paths that wind around the property and into the forest. Sunsets from the porch are amazing and the outdoor shower was lovely! It was an absolutely magical place to rest at after tent camping in Acadia for a week. Matt and Emily are gracious hosts who live on the property (which is around 18 acres). While we were out for a stroll, we met Matt and his kiddos. They’re so sweet! He told us a bit about the property and offered us some honey that was harvested right there on the property! If you get a chance, go to the the Main Street Creamery in Bridgton. Amazing ice cream! If you’re into beer, Oxbow brewing is a must! The bookstore in town is pretty cool too! We will definitely be back in the future! Thanks for an amazing visit friends!

The Strawberry house was such an amazing place for my wife and I to spend our first anniversary. We go to midcoast Maine every year and this was certainly a special one for us. Comfortable, thoughtfully designed and accessible to town. Highly recommend!

My husband and I stayed here with our dogs and loved it! The cottage was quaint and lovely …. And the location is perfect! Amanda was so kind and responsive! We will definitely be back when in Camden again 🌸🌲🌊

We loved our stay at Anne’s place! It’s a beautiful neighborhood close to the water. Our kiddos were able to walk down at low tide to play in the sand and catch crabs. The market next door was so convenient for quick but delicious meals after a long day.

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!

Aimee was wonderful to deal with. Her place was absolutely beautiful. we definitely picked the right place. the sunrises were so awesome. Rockland was a gorgeous little town.

The home was beautiful and exactly as pictured. We especially loved the hot tub and the outdoor fire pit, such great touches for a relaxing stay. The space had everything we needed, and we felt right at home. We’d absolutely stay again in the future if welcomed back!

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.

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 had a lovely time at the cabin. Close to skiing yet peaceful and relaxing. We thoroughly enjoyed our stay ! Thank you!

Rockland, June 2025 The house was spacious and comfortable. The house is well stocked and clean. Rockland is a nice area that we plan to visit again.

We had a great time at Jim and Gwens place in Knight's Hill. The amenities were great and the location provided us with everything we were looking for near Moose Pond. Would highly recommend.