Kid-friendly holiday rentals in Chatham

Find and book unique family-friendly rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Chatham family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Wellfleet
4.72 out of 5 average rating, 50 reviews

Wellfleet, MA. Cape Cod sleeps 8

MikeRating, 5 stars3 months ago
Clifford's place worked out perfectly for my crew that was working in the area for a multi week project. I would definitely book again if we have more work in the area.
Superhost
Home in North Eastham
4.78 out of 5 average rating, 18 reviews

The Sandpiper

AndrewRating, 5 stars8 months ago
Easy access to restaurants, grocery stores, beach and mini golf! Great area to take a walk or run around the neighborhood. Had all the basic supplies for cooking and comfortable furniture in the living room and bedrooms. The outdoor patio and yard is where we spent most of our time, the chairs and set up was perfect. The outdoor shower is a nice touch too!
Superhost
Home in Marstons Mills
4.88 out of 5 average rating, 133 reviews

The Mills Retreat- 3BR/2Bath - Beach pass included

JulieRating, 5 stars4 months ago
This was a family Christmas getaway, and it was perfect.
Top guest favourite
Home in East Falmouth
5 out of 5 average rating, 36 reviews

Spacious and immaculate custom home.

LeslieRating, 5 stars8 months ago
We had a fantastic family vacation in Falmouth and Anne’s house greatly exceeded all of our expectations! Comfortable, beautiful decorated and appointed with every amenity. We will be back!
Superhost
Home in Sandwich
4.77 out of 5 average rating, 26 reviews

Holiday in the sun!

KaylaRating, 5 stars1 week ago
Craig was awesome and extremely nice and understanding! The house was clean and one of the best I have stayed in. The location is quiet and tucked in a small neighborhood. I had the most amazing stay and would suggest this to anyone going to this location!
Superhost
Home in Wareham
4.75 out of 5 average rating, 187 reviews

Quaint Oceanside Cottage with Boat Mooring

Brian Rating, 5 stars7 months ago
Beautiful location with great views while sitting by fire pit or even from inside house. Split level allows for some alternative sleeping arrangements which worked great for us. Listing spot on with description and photos. As advertised. Host quick to respond to inquiries. I would highly recommend. I would to stay here again. Thank you
Guest favourite
Home in Teaticket
4.93 out of 5 average rating, 122 reviews

Cute Single Family Home in Nice Neighborhood

NicoleRating, 5 stars6 months ago
This little beach oasis is such a great value! We thoroughly enjoyed our stay here. As mentioned in the description, Patty & Bruce's spot is legitimately only a few minute walk from multiple beaches and is in such a cute little neighborhood! They have plenty of beach items should you not bring your own, which is great. The space itself is perfect for a quick little weekend getaway.
Superhost
Home in Falmouth
4.75 out of 5 average rating, 4 reviews

NEW! 2 Houses, Main House plus Guest House

CassandraRating, 5 stars8 months ago
We stayed here with a large group of friends including toddlers and babies for a friend’s wedding. We loved the space, especially sitting out on the deck together, having two separate spaces so some friends could stay up chatting while the kids slept in the other house was excellent. We would highly recommend this house for a fun and relaxing group trip!

Family-friendly apartment rentals

Guest favourite
Flat in Wellfleet
4.88 out of 5 average rating, 146 reviews

In the Heart of Wellfleet and Walk to Mayo Beach

AndrewRating, 5 stars6 months ago
wonderful property in beautiful town. Great location on Main Street with walking access to all the amenities. Frances was very accommodating with great advice for travellers.
Guest favourite
Flat in East Dennis
4.86 out of 5 average rating, 153 reviews

Peace By The Bay

JohnRating, 5 stars5 months ago
Great apartment. Close to the beach and great restaurants, but also quiet and peaceful. Slept better here than I do at home.
Guest favourite
Flat in Chatham
4.93 out of 5 average rating, 216 reviews

Charming Downtown Chatham Apartment

WillRating, 5 stars7 months ago
Had a great stay in Chatham at this Airbnb. Heather the host was extremely friendly and made us feel very welcome. The place was very well located in Chatham, well appointed and comfortable. We were very happy with our stay there, including a pack and play for our 16 month old. Would highly recommend a stay here to anyone.
Guest favourite
Flat in Barnstable
4.95 out of 5 average rating, 120 reviews

Centerville Studio with Town Beach Pass

CarrieRating, 5 stars1 month ago
Great home for our superintendent to stay in while working on a project. Highly recommend!
Top guest favourite
Flat in New Bedford
4.99 out of 5 average rating, 119 reviews

One Bedroom in-law near beach with breakfast

LexyRating, 5 stars1 month ago
I had an incredible experience staying at Monica and TJ’s place! From the moment I arrived, everything was seamless. The check-in process was smooth, and the home was exactly as described—clean, cozy, and beautifully decorated. The location was perfect, making it easy to explore the area. The host was incredibly accommodating and responsive, ensuring I had everything I needed throughout my stay. The little touches, like [mention any standout amenities, e.g., complimentary snacks, extra towels, a well-stocked kitchen], made the experience even better. I would highly recommend this Airbnb to anyone looking for a comfortable and enjoyable stay. I’ll definitely be booking again in the future!
Guest favourite
Flat in Falmouth
4.95 out of 5 average rating, 170 reviews

Your Private Garden

KotaroRating, 5 stars6 months ago
Mary Alice's place is so charming, equipped with everything I needed in daily life, and surrounded by full of green and peaceful neighbors. She is also very responsive and supportive in the communication. Definetely recommend, and wish to come back again!
Superhost
Flat in Nantucket
4.77 out of 5 average rating, 175 reviews

Cozy studio-apartment

SarahRating, 5 stars6 months ago
Irina is easy to communicate with. The place is very clean, just as described. Comfortable and has everything you need for a short stay. Bathroom is very nice and clean. Location is very accessible to downtown by Uber, takes less than 10 min. Walking distance to downtown is about 1.5 miles and it is a safe and mostly paved walk. Area feels safe, a little loud as it is near the street and above the cafe but nothing that was really disturbing of sleep. Thank you!
Superhost
Flat in Hyannis
4.89 out of 5 average rating, 137 reviews

Perfect Location! Modern Hyannis Center Apartment!

PhilipRating, 5 stars2 months ago
Had a great time staying at this spot in Hyannis. Easy to walk to plenty of restaurants and attractions in the area, it was exactly what we were looking for.

Family-friendly apartment rentals

Guest favourite
Apartment in Brewster
4.97 out of 5 average rating, 178 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

KathleenRating, 5 stars5 months ago
It is always comforting to stay at Anna’s condo. It feels like home with well thought out amenities, clean spaces, quiet surroundings and such a helpful host. It is a great space for families and has all you need to cook in. I highly recommend staying here.
Guest favourite
Apartment in Dennis Port
4.94 out of 5 average rating, 169 reviews

#6 Ocean Oasis Studio, 300 Yards to Glendon Beach

MarciaRating, 5 stars6 months ago
What a darling space! We felt right at home. It was quiet and cute inside and we were able to really relax. Thank you, Sam for such creating an inviting living area!
Guest favourite
Apartment in Chatham
4.86 out of 5 average rating, 100 reviews

Steps to Private Beach in Chatham

HannahRating, 5 stars1 month ago
We absolutely loved our stay at Julia’s home! It was in amazing location close to the beautiful downtown but also very private. The private beach is hard to beat! The space was clean, exactly as pictured, and was stocked with anything you could need. Julia was an amazing host who provided clear instructions and responded quickly. We can’t wait to return for our next stay here. Thanks again Julia!!
Superhost
Apartment in Provincetown
4.91 out of 5 average rating, 211 reviews

Romantic Seaside Escape InThe Heart Of P-town

StevenRating, 5 stars5 months ago
Debra had a beautiful apartment in a perfect location. The balcony was especially enjoyable. It was very clean and had everything you could possibly need.
Guest favourite
Apartment in Dennis Port
4.86 out of 5 average rating, 199 reviews

The 5 minute walk to beach Super Cute Beach Condo

ConorRating, 5 stars2 weeks ago
Perfect space for a long weekend or low key beach trip. Walking distance to the beach and very quick drive to other restaurants, bars, coffee shops, etc. While the space is smaller it has all the amenities to handle everything you’d need like a full kitchen, grill, etc. We went in the offseason and still found plenty to do but you could tell the area would be more active during the peak cape season.
Guest favourite
Apartment in Provincetown
4.93 out of 5 average rating, 100 reviews

Modern, clean waterviews

JacobRating, 5 stars10 months ago
This was my second stay at Garrett’s and the place was just as nice as I remembered (plus a a few upgrades). Garrett’s always quick to respond to inquiries, unit had just about everything we needed including beach towels and location is great as it’s a short bike ride from center town and peaceful/quiet if you’re looking for a balanced vacation.
Guest favourite
Apartment in Brewster
4.88 out of 5 average rating, 239 reviews

Shining Sea Condo

JanetRating, 5 stars2 days ago
We were on the Cape to celebrate my mother’s 98th birthday. This was a perfect place for my husband and I as well as our daughter with our 5 month old grandson.
Guest favourite
Apartment in Provincetown
4.86 out of 5 average rating, 118 reviews

Commercial Street Cozy 1/1 In The Center of Ptown!

JonRating, 5 stars3 months ago
We truly enjoyed our stay at this charming, clean apartment. It was the perfect size for two people and the location on Commercial Street was ideal for accessing everything in Ptown. Paul was proactive in ensuring we had everything we needed and answered questions promptly. Thank you!

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

  • Total rentals

    120 properties

  • Nightly prices starting at

    £45 before taxes and fees

  • Total number of reviews

    4.9K reviews

  • Family-friendly rentals

    120 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Destinations to explore