Family-friendly holiday rentals in Randolph

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Randolph family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Condo in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars4 weeks ago
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again
Guest favourite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars3 weeks 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 favourite
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars3 weeks ago
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars1 day ago
Brad was very friendly and helpful. Beautiful home!
Top Guest favourite
Home in West Hyannis Port
4.97 out of 5 average rating, 155 reviews

Luxury House 0.25 mi from Craigville Beach

AngieRating, 5 stars1 month ago
I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!
Top Guest favourite
Home in Oak Bluffs
4.93 out of 5 average rating, 199 reviews

Spectacular beach & pool combo; beautiful sunsets!

RobynRating, 5 stars6 days ago
Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.
Guest favourite
Apartment in Oak Bluffs
4.93 out of 5 average rating, 137 reviews

Victorian Oasis: Driveway, hot tub, grill & more

SaraRating, 5 stars1 day ago
My husband and I and our small dog had a fantastic stay. Sharon accommodated a (very!) early morning checkin time and was very responsive and clear throughout our stay. The unit suited our needs well and we absolutely loved spending time in the back patio/garden area.
Guest favourite
Villa in Uncasville
4.89 out of 5 average rating, 403 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

MalloryRating, 5 stars1 week ago
Very cute tucked away villa, with pool/hot tub, close to Mohegan Sun. The host was very responsive and the villa was clean and nicely decorated. Would love to come again :-)

Family- and pet-friendly home rentals

Top Guest favourite
Apartment in Lakeside Marblehead
4.94 out of 5 average rating, 196 reviews

Two bedroom Apt with a deck

EmilyRating, 5 stars3 days ago
We had a great stay here! Very flexible check in, the comfiest beds and a variety of incredible books to choose from if you’re staying in!! The host was very sweet and even gave us a recommendation for a great spot to watch the full moon that evening. Gorgeous gardens in the back. Highly recommend this stay!
Guest favourite
Condo in Newport
4.92 out of 5 average rating, 691 reviews

Boutique Hotel Special pricing available

SelinaRating, 5 starstoday
We had a lovely stay at Pelham Court! The location was the perfect spot to be near the main attractions around Thames Street and convenient to walk elsewhere. We loved having a private parking spot for our car as well. Bonus perk for being able to bring our dog with us! The hosts checked on us every evening if we needed anything—provided recommendations, and were super friendly and welcoming! Only downside to being so close to downtown is the loud noise from a nearby bar late at night on weekend. Overall, we enjoyed our stay in Newport/Pelham Court and hope to come visit again in future! Thanks for having us! :)
Guest favourite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months ago
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.
Top Guest favourite
Cabin in Rockport
4.97 out of 5 average rating, 454 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

JasonRating, 5 stars3 weeks 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 favourite
Apartment in Milton
4.85 out of 5 average rating, 119 reviews

Retreat Milton/Boston line (transit close) Pets

GeraldineRating, 5 stars7 months ago
We were a group of four guys on a sports-trip to Boston. The location was perfect, 30 minute drives from Downtown, Foxborough and Boston College. Lovely neighbourhood, quiet and nice walks nearby. The house was as described in the listing, plenty of space for four, clean and comfortable with a well-equipped kitchen.
Guest favourite
Guest suite in Charlton
4.86 out of 5 average rating, 417 reviews

Baker Pond Hideaway

JohnRating, 5 stars2 days ago
My friend and I always enjoy our time at this beautiful home. Appointed with everything we need for a fun weekend! Just wish we could of spent a little time with our amazing hosts!
Top Guest favourite
Cabin in Voluntown
4.95 out of 5 average rating, 743 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

ChristineRating, 5 stars5 days ago
Great camp and peaceful area. Angela is a great host and very accommodating. I have stayed twice and would definitely come back again.
Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 159 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

AngelaRating, 5 stars2 weeks ago
The house is amazing! It has everything that you would need and is so comfortable. The property is peaceful, and it feels like you’re on your own little island while still being minutes from stores and restaurants. We had a perfect weekend celebrating some milestone birthdays in our family.

Family-friendly home rentals with a pool

Top Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 56 reviews

Our families slice of heaven

EmilyRating, 5 stars7 months ago
This place was INCREDIBLE!! Marla and her family were so responsive and so welcoming!! This house was the cleanest I have ever stayed in. The furniture was so comfortable and cozy. I would HIGHLY recommend staying here! I hope to come back in the near future!! Thank you Marla and family for being such amazing hosts!!
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 238 reviews

Cedar Ridge: House or House+Apartment

HilaryRating, 5 stars1 month ago
Very responsive hosts who helped us with restaurants. House was very clean, well appointed and had everything we needed. Great for families or a girls weekend!
Guest favourite
Guest suite in Brooklyn
4.93 out of 5 average rating, 190 reviews

Affordable In-Law Apartment in Brooklyn, CT

LyndaRating, 5 stars3 weeks ago
Thank you so much! Really enjoyed my time in brooklyn.
Superhost
Townhouse in Middletown
4.97 out of 5 average rating, 36 reviews

Townhouse Close to Downtown Newport & Beaches

LydiaRating, 5 stars2 days ago
Absolutely beautiful space! Very comfortable and cozy! We enjoyed every bit of our visit and felt so at home. It's also in the perfect location: close enough to downtown Newport that everything is very accessible and it's also in a quiet, peaceful neighborhood for a good night's rest. But wait--there's more! Kristin was by far one of the most proactive, friendly, and helpful host I've ever experienced with Airbnb! I highly recommend this listing!
Superhost
Apartment in Brooklyn
4.85 out of 5 average rating, 221 reviews

8 Bedroom, 4 full bath residence with 40' pool

Maria ChristinaRating, 5 stars1 week ago
The hosts Marybeth and Douglas were so welcoming to us and accommodated our request to check- in earlier than scheduled! They were very friendly and provided extra stuff to make our stay feel so homely and comfortable! Everyone of us (13 people) truly enjoyed our stay at their beautiful, spacious and historical home!
Superhost
Condo in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.
Top Guest favourite
Home in Cotuit
4.95 out of 5 average rating, 115 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

JorgeRating, 5 stars1 week ago
Beautiful house. Kid friendly Really close to the beach Amazing hosts
Guest favourite
Apartment in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars1 week ago
We had a wonderful stay! It's very close to Boston, and other area attractions like Salem and beaches, but still peaceful. We enjoyed sitting at the pool. Kathy was very responsive and checked in with us to make sure we had everything we needed. They provided clear instructions for getting into the space and I had no issues navigating in and out of the neighborhood or to the basement apartment. I would definitely stay again if I'm needing a place in the area!

Quick stats about holiday rentals that are family-friendly in Randolph

  • Total rentals

    20 properties

  • Nightly prices starting at

    $116 NZD before taxes and fees

  • Total number of reviews

    750 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore