Some info has been automatically translated. Show original language

Family-friendly vacation rentals in Winthrop

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Winthrop family-friendly rentals

Family-friendly home rentals with a hot tub

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Guest favorite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars6 days ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Guest favorite
Home in Hopkinton
4.95 out of 5 average rating, 154 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 month ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Top guest favorite
Home in Newbury
4.98 out of 5 average rating, 51 reviews

Plum Island - Luxury Beach House

TracyRating, 5 stars9 months ago
We rent a house on PI every year and this house was perfect for us. We could walk to the basin with our SUP’s, easy walk to beach and stores and ice cream! We loved the double outdoor shower option for the kids after a long sandy day at the beach and they supplied all the beach toys, umbrellas and chairs! The rooftop deck was our favorite part we watched the sunset every night. We would rent this house again if the dates line up!
Home in Gloucester
4.9 out of 5 average rating, 10 reviews

Steps to Good Harbor Beach

MichaelRating, 5 stars71 months ago
Kate's house in Gloucester is an ideal place to experience one of the best beaches on the North Shore. Kate's home accommodated the eight of us very comfortably; the proximity to the beach was second to none and Kate and Michelle's response to a couple of minor issues we had was expeditious and friendly. There aren't enough superlatives I could use to recommend Kate's place.
Superhost
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars2 weeks ago
We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.
Superhost
Apartment in Roxbury
4.78 out of 5 average rating, 326 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

KatieRating, 5 stars1 month ago
Alex’s place was wonderful and a perfect location for someone who wants to travel Boston on foot. Very close to the T which made getting around really easy. Alex was also a very flexible, responsive, and kind host for our stay. Would definitely stay there again!

Family- and pet-friendly home rentals

Top guest favorite
Home in Wakefield
4.96 out of 5 average rating, 263 reviews

Welcoming 7-room house <15 miles to Boston & Salem

EmilyRating, 5 stars3 weeks ago
We loved staying here! Plenty of space for our family of 6, including one little one. It was exactly as pictured and well-stocked with spices in the kitchen and shampoo etc in the bathroom! Beds were super comfy and we loved how close it was to the lake, restaurants, and a playground. Would definitely stay here again!!
Top guest favorite
Cabin in Rockport
4.97 out of 5 average rating, 453 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

JasonRating, 5 stars1 week ago
Wonderful getaway in the woods, but close to restaurants and shop in Rockport. We loved being greeted by the dogs and the hiking trails right outside the front door are amazing.
Guest favorite
Apartment in South End
4.96 out of 5 average rating, 378 reviews

Charming South End Duplex (Pets Ok)

KaitlynnRating, 5 stars1 week ago
Absolutely amazing place to stay! The host is sweet and responsive and it's in a great area :) lots to do just by walking around. My groups and I had a great time here and would come back again!
Guest favorite
Home in Ipswich
4.89 out of 5 average rating, 108 reviews

Hillside Ocean View 2BR with Private Beach Access

PeterRating, 5 stars1 week ago
Just steps from a private beach in a secluded corner of the North Shore, Mark's house was a perfect place to rest, explore, and spend a long weekend in one of our favorite parts of the world. The house is comfortable and welcoming, and everything was easy. Looking forward to returning!
Guest favorite
Townhouse in Allston
4.93 out of 5 average rating, 187 reviews

Sparkling Condo With Modern Amenities

AllisonRating, 5 stars9 months ago
Michelle was very responsive and great at communicating leading up to our stay. The house was easy to find, good neighborhood, perfectly clean and had everything we needed. Parking was included which was awesome. The T was easy to walk to so we could go downtown every day easily. The host recommendation for Lulu’s Allston was spot on, it was nearby and great. We felt right at home and had a wonderful stay and check out was also easy. Thank you Michelle for hosting a wonderful place!
Guest favorite
Home in Salem
4.95 out of 5 average rating, 153 reviews

Quaint Little New Hampshire Lake House Getaway!

KevinRating, 5 stars1 week ago
We really enjiyed our stay and would recommend to anybody else.
Superhost
Home in Medford
4.84 out of 5 average rating, 139 reviews

Sunny home minutes from Boston. Free parking.

EricRating, 5 stars2 weeks ago
Nice two-night family stay in this Medford neighborhood to coincide with Tufts graduation. Easy parking with convenient proximity to other commercial areas. Hosts were proactive in trying to address a temporary problem with the TV before we checked in - we had no plans to use the TV but appreciated the outreach and intention to address quickly. No problem during the stay but had the confidence that we could have reached out if there were any problems.
Guest favorite
Apartment in Cambridge
4.87 out of 5 average rating, 441 reviews

Cambridge Getaway @ Harvard & MIT

KarenRating, 5 stars1 week ago
We loved our stay at Kevin's historic Cambridge home! The 2-bedroom apartment was lovely, clean, and had plenty of room for me and my teenage son, and I loved the cute rooftop deck for my morning coffee! The neighborhood is very pretty, and I felt safe walking alone to the Inman Square shops, local coffee shops, and the subway. Kevin is a very kind and responsive host, and he had coffee & creamer, beer & wine, and cookies for us! The apartment was so much better than staying in a hotel room, and we plan to stay at Kevin's the next time we visit my daughter in Cambridge.

Family-friendly home rentals with a pool

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Guest favorite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars6 days ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Guest favorite
Home in Hopkinton
4.95 out of 5 average rating, 154 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 month ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Top guest favorite
Guesthouse in West Roxbury
4.95 out of 5 average rating, 194 reviews

Country Cottage in the City

MariaRating, 5 stars6 days ago
What a perfect weekend in a private cottage by the pool. Although the weather did not cooperate for pool time, Mark & Susan’s cottage was a perfect place to have a central location outside of Boston. You would never know you were close to the city. Absolutely lovely! Their cottage was super clean and inviting and lacked nothing necessary for a long weekend away. They were very proactive in communicating with us about checking in and if we needed anything during our stay. Really terrific!
Superhost
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
Apartment in Winthrop
4.96 out of 5 average rating, 312 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

AndréRating, 5 stars5 days ago
The apartment was exceptionally clean, and exactly as shown in the photos. It had everything I needed for a comfortable stay — from a well-bathroom to a cozy bed and reliable Wi-Fi. The location was also a big plus: safe and quite. Katy, was a fantastic host — very responsive, friendly and proactive. They reached out to make sure everything was going well and answered any questions I had quickly and clearly. It really made the whole experience feel smooth and stress-free. Overall, I’d absolutely recommend this place to anyone looking for a comfortable and reliable stay. I’d be happy to return on my next trip!
Guest favorite
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars2 weeks ago
We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.
Guest favorite
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

MichaelRating, 5 stars5 months ago
Our second time, weeklong stay! And we hope to do it again next year. Just simply meets our needs very well. It's a joy to stay here!

Quick stats about vacation rentals that are family-friendly in Winthrop

  • Total rentals

    70 properties

  • Nightly prices starting at

    $100 before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi

Destinations to explore