
Family-friendly vacation rentals in Woolwich
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Woolwich
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Woolwich family-friendly rentals
Family-friendly home rentals with a hot tub

Raven's Crossing - Kate's Cottage
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!

Stunning & Spacious 6BR Waterfront House + Hot Tub
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.

Tree Dwelling with Water Views & Cedar Hot Tub (2)
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

Brownie- Comfy Modern Ranch Home w/Hot Tub
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.

Luxury Beach House Old Orchard Beach Maine
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!

Private studio loft, decks and hot tub
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.

Cozy hot tub haven
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

Nashport on the Penobscot
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.
Family- and pet-friendly home rentals

Charming Victorian farmhouse 1880's bedrooms-2
Marcia’s place is very cozy and charming. Plenty of space and a comfortable accommodation. Would stay here again.

Charming Home Getaway near Sunday River & Hikes
amazing stay! hosts were awesome and place was exactly as described. would stay here again!

Fire Fly Yurts on Funky Bow Lane
Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

Private Maine Camp
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.

Classic Maine, Modern Comfort
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.

Charming Portland Colonial, In Town
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!

Monument SWEET!
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!

Unique artist's sun filled farmhouse meets loft
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.
Family-friendly home rentals with a pool

Campbell Cottage at Poland Spring Resort
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.

Caribou Run Private Retreat with Mountain Views
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.

Million $ views, Hot Tub, Waterfront, 14 acres WOW
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

Sunday River Condo - Brookside I A-408
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

Sunday River Resort Condos @Cascades
Great place to rent with easy ski in and out from the mountain!

The Hill's on Buttonwood
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

Large private area, close to Rockland
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.
Quick stats about vacation rentals that are family-friendly in Woolwich
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
1.9K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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