Family-friendly holiday rentals in Wiscasset

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!

This is as picturesque of a ski cabin as they come. Everything was clean and tight. Far enough into the mountains with a clean up to date feel including Lutron radio RA3 switching. Cleaning fees were a little steap, but we are clean and neat people so im sure they are set to expect the worst. 10 for 10 would rent this house again.

Just returned from the most fantastic 2 weeks exploring the US which included a weeks stay at Kiwi Lodge. Where to start? This was exactly as described and the perfect base for exploring Maine. The property was spotless and has all the amenities needed for a comfortable stay. 3 beautiful bedrooms, 2 great sized bathrooms, wonderful living area and kitchen and fantastic games room. Hot tub was brilliant. The location on the lake is just perfect, we had the lake to ourselves and took the canoe out. Nearest town of Farmington has all the shops and cafes you’d need. The communication from Kay was great from the day we booked, and recommendations we took her up on were all absolutely spot on. Thank you Kay and thank you Kiwi Lodge for a holiday to remember!

Large, bright, spacious beach house just steps from the beach and a short walk from the more bustling areas of OOB. Ocean views from all floors. Spacious enough for groups to be together but also to have some privacy if need be. Comfortable beds and well stocked kitchen. Lovely patio with spacious hot tub, outdoor dining area and small yard. A great spot with a responsive host!

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

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.

What an incredible home to stay at! Neal and Krystal provided everything one needs! Fresh clean sheets, towels, and the kitchens were fully equipped with all your needs. Plenty of space for the 12 of us that went up there. The insides is completely renovated with great amenities. Not to mention they left us local refreshments and snacks for arrival! All of those who went up were blown away by this house and many have expressed returning before we even left! This house is located in a great place as well. It’s a quick walk to the pier and all the local favorite places to go too! If you are looking for a home to stay in OOB for a fantastic price, don’t wait to book this home. Krystal and Neal are also extremely friendly and communicative. They truly went above and beyond to make sure our stay was truly memorable. I cannot thank them enough!

Marcia was wonderful . accommodated my wishes. It was like I was in a dream The place was pristine and beautiful would love to return 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 cabin was a wonderful place to spend the week, and I couldn’t be more happy. The hosts were communicative and friendly; offering great local recommendations. My girlfriend and I would be more than happy to stay here again!

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!

A group of 5 of us stayed at Kathy's listing and felt like we had plenty of room. We were all comfortable and found the location to be great with plenty to do within walking distance. Some of the doors were glass with blinds/shades that weren't entirely opaque so we had to be somewhat mindful when changing in our room. The front door battery was dead when we arrived and so the door was unlocked but this was quickly resolved with the help of the host and extra batteries on site. Location was fabulous and peaceful. No issues with finding free street parking, either. Overall, we enjoyed our time here and would stay at this listing again!

Great retreat to feel relaxed and inspired. The location suits our needs for comfort and accessibility to surrounding disc golf courses and is great for travelers looking to escape screens, and the stress of cluttered and busy lifestyles. It feels like home as soon as you arrive .

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.

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!

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!

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

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

My husband and I, and our two pups had a fantastic time in the Carriage House for a week. Part of a breathtaking private/secret compound on the water…with the most incredible private tidal pool. The place is so authentic, which is what we love about staying in ME when we can escape. We were so blessed to find Margaret’s place last minute. Margaret’s mother, Sally, and her husband were in the main Kate’s house. So so sweet they were to us and our girls. A dog paradise. We are foodies. Plenty of good restaurants around - just a few minutes to the adorable village of Stonington. Around the corner is one of the best restaurants in the country - Aragosta. We can’t wait to return…hopefully, in the Fall. A trip we will always remember. Thank you, Margaret & Family.

We had a great time at Teri’s place. The condo was described exactly, clean and had everything that we needed. The beds and furniture were. very comfortable. The view from the balcony was beautiful with nice chairs set out to enjoy your coffee. It was a 30 second walk to the beach, which was great for having a Toddler. The pool and laundry was a plus. When we head back to OOB we would stay again.