Kid-friendly holiday rentals in Winthrop

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Winthrop family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Farmington
4.97 out of 5 average rating, 219 reviews

Carriage House

SarahRating, 5 stars2 weeks ago
I think I was one of the first here, so I count myself lucky. the carriage house is very quiet, I never heard outside noise. Absolutely no problem going to sleep, no ambient noise or light. Comfortable stay. Easy access and parking right outside the door. Full size refrigerator and stove. This rental would be fantastic for longer stays. Highly recommend.
Guest favourite
Home in Sumner
4.96 out of 5 average rating, 135 reviews

Quiet and Private in Oxford Hills – Dog Friendly!

RaijueneaRating, 5 stars2 weeks ago
Amazing place, host was super kind and accommodated my family’s last minute booking since we were cancelled on twice that week! We are super happy we found this adorable beautiful place that ended up being better than the other places would have been anyway!
Top guest favourite
Home in Bridgton
5 out of 5 average rating, 103 reviews

Wren Cabin + Wood fired Sauna

WillRating, 5 stars1 week ago
Our stay was so relaxing. The house is very comfortable and we felt at home right away. Kitchen had everything we needed to prepare meals. The sauna is absolutely magical and the lake was quiet and peaceful. Check in/out was a breeze. Perfect spot for a relaxing long weekend with zero stress.
Guest favourite
Home in Buckfield
4.9 out of 5 average rating, 203 reviews

The Nifty Village House

AndrewRating, 5 stars2 weeks ago
It was a perfect place to stay for our weekend adventure. The place was very clean and tidy. It was obvious that a lot of work and thought was done to make it a really great home. I would definitely rent again when my travels take me back to the area.
Top guest favourite
Home in Pittston
4.99 out of 5 average rating, 146 reviews

Riverside

MarleneRating, 5 stars2 weeks ago
This was my 5th time going there and I love it! The house is so cozy & very clean. The property is large and the view is breathtaking over looking the river. They are also pet friendly so we were able to take our Lhasa Apso Revy on vacation with us. Besides how great this Air BnB is, my favorite is the hosts Kent & Tish! They are wonderful people. They are kind & friendly, & have such beautiful souls. They have become family to me! I highly recommend getting this air bnb!! Thank you again Tish & Kent! Ian, Revy, & I are always happy to see you!!
Guest favourite
Home in Augusta
4.95 out of 5 average rating, 154 reviews

Lakefront: Private Hot Tub, Sauna & Free Massages!

TomRating, 5 stars3 weeks ago
What an AMAZING stay! We loved staying at the lake house and enjoyed extra that came with it! The bed was comfortable, the rooms were all beautifully decorated and we both loved the hot tub! Although it rained almost the entire time we were able to enjoy the game room and the fire place. We have already told our friends and family how much of a great stay we had!
Guest favourite
Home in Litchfield
4.92 out of 5 average rating, 137 reviews

Beautiful lake house on Tacoma Lakes near Coast

DannyRating, 5 stars2 weeks ago
What a place. So many great things to do. We swam and fished in the lake, the kayaks and canoes were so much fun and at night we sat by the fire pit and played table hockey.The house had everything we needed. The host was very responsive and answered all questions quickly.
Guest favourite
Home in Lisbon
4.94 out of 5 average rating, 426 reviews

Unplug at a Beachy Bolthole with Classic New England Style

TylerRating, 5 stars4 days ago
This place is very nice and is perfect when visiting places north of Portland, such as LL Bean and some nice state parks. Very clean and quiet. There are stairs as soon as you enter the unit, but weren’t an issue for me. Would definitely stay here again if in Portland area!

Family-friendly apartment rentals

Guest favourite
Flat in Damariscotta
4.92 out of 5 average rating, 286 reviews

Fernald's Backside

KriyaRating, 5 stars1 month ago
We had a great stay at Sumners place. It's location is very cool being right downtown but at the same time it is quiet and peaceful. He has it set up with everything you need and more. We appreciated his friendliness and great communication!
Guest favourite
Flat in Richmond
4.91 out of 5 average rating, 267 reviews

The Barn by Swan Island: Whimsical, Comfy, & Fun!

RebeccaRating, 5 stars1 week ago
Lovely, comfortable stay with thoughtful decor and hospitality. Close enough to Portland and outdoor adventures while feeling quiet, peaceful and away from it all.
Top guest favourite
Flat in Boothbay
4.97 out of 5 average rating, 323 reviews

Sunnymeade

SamanthaRating, 5 stars2 days ago
Robert’s place was the perfect getaway for me calm, quiet, and peaceful. Everything was perfect, the space was cozy and neat, it had everything I needed for a few days away. Quick drive to the harbor with lots to do if one chooses. Hoping to make it back there soon.
Top guest favourite
Flat in Waterville
4.99 out of 5 average rating, 173 reviews

Sweet Retreat: 2 BDR Home Mins to Colby

KatieRating, 5 stars3 months ago
We had a great stay. The location was ideal and everything we needed was supplied. The house was exactly as pictured and well stocked and very clean. Chelsey was very responsive to any questions and they also dropped off some very thoughtful sweet treats! Highly recommend and we would definitely stay again!
Guest favourite
Flat in Wilton
4.93 out of 5 average rating, 264 reviews

Apt above Ambition Brewing in Downtown Wilton

JoanneRating, 5 stars1 month ago
Great spot at the center of Wilton. Comfortable bed. Close to restaurants. Responsive and courteous host.
Guest favourite
Flat in Topsham
4.9 out of 5 average rating, 134 reviews

King Size Bed - Hip Studio On Winter St - Topsham

RebeccaRating, 5 stars2 weeks ago
Very happy with my stay here, host was very responsive and helpful. Very quaint, peaceful, clean space!
Guest favourite
Flat in Pittsfield
4.89 out of 5 average rating, 100 reviews

Loft Retreat

MarkRating, 5 stars1 week ago
This Airbnb was exactly as listed. Everything is updated, very clean, and comfortable. Jordana was very responsive and accommodating. I would stay here again.
Guest favourite
Flat in Edgecomb
4.86 out of 5 average rating, 484 reviews

Waterfront Condo at the Sheepscot

MaryRating, 5 stars1 day ago
Audrey’s place was right across the water from Wicasset and a quick drive to Boothbay Harbor where we did a Puffin cruise. Great place to stop for the night.

Family-friendly apartment rentals

Guest favourite
Apartment in Bartlett
4.87 out of 5 average rating, 303 reviews

Attitash Studio | 5min to Storyland| Pools

JasmineRating, 5 stars4 days ago
Was a nice peaceful stay for the most part. The pools were nice to swim in although it seems not everyone seemed to want to follow the pool rules. Doesn't help that there were no lifeguards to ensure kids remained safe other than the parents. A few times I saw individuals in the pool water with either glass or an open drink in hand. Saw kids diving into the pool and even witnessed a few hurt themself. But other than that, the hot tub was so lovely to soak in. The arcade room was fun to play in. It was cool to see there was a lot to be able to do in the area for yourself. Definitely wish there was more to do in the area other than the classic tourists spots. A lot of beautiful spots to hike. We ended up checking out Diana's Bath and it was a gorgeous spot to watch cascading waterfalls or have a tiny dip. Would definitely check out this space again and maybe spend a few more days to truly appreciate the environment and mountains ^-^
Guest favourite
Apartment in Old Orchard Beach
4.9 out of 5 average rating, 105 reviews

Oceanfront Condo with Awesome Views

karriRating, 5 stars2 months ago
Great stay
Guest favourite
Apartment in Conway
4.83 out of 5 average rating, 175 reviews

Cozy condo with North Conway at your finger tips!

EricRating, 5 stars3 weeks ago
Thank you for letting us stay with you. We had a fantastic weekend
Guest favourite
Apartment in Bartlett
4.92 out of 5 average rating, 461 reviews

Across from Storyland & in the Heart of the Mtns

MonamiRating, 5 stars3 weeks ago
Beautiful place, has everything you might need. Very convenient location , close to storyland, restaurants and convenience stores . The restaurant recommendations from the host were great
Guest favourite
Apartment in Old Orchard Beach
4.73 out of 5 average rating, 119 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

SharonRating, 5 stars5 months ago
This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.
Top guest favourite
Apartment in Bartlett
4.99 out of 5 average rating, 142 reviews

KimBills’ on the Saco

SaraRating, 5 stars3 months ago
We are a family of four and we stayed for four nights. It was larger than we expected and we were all quite comfortable. We loved that we could ski, swim, and have dinner without getting into our car on an extremely frigid (-17 degree windchill) day! It was a fun atmosphere and we loved our stay!
Top guest favourite
Apartment in Damariscotta
4.89 out of 5 average rating, 164 reviews

River Escape - Studio Apt. with River Access

MarlaRating, 5 stars1 month ago
Lovely stay in a cozy place during a harrowing move. Cozy place provided just what we needed.
Guest favourite
Apartment in Bartlett
4.93 out of 5 average rating, 268 reviews

An Amazing Mountain Getaway!

KelseyRating, 5 stars1 week ago
My family and I had an amazing weekend. Melissa was very responsive and flexible with checking in/out. Everything was clean, plenty of linens and towels, great location, comfy beds. 10/10. We can’t wait to be back!

Quick stats about holiday rentals that are kid-friendly in Winthrop

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹3,425 before taxes and fees

  • Total number of reviews

    860 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

Destinations to explore