
Kid-friendly holiday rentals in Brewster
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Top-rated family-friendly rentals in Brewster
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Popular amenities for Brewster family-friendly rentals
Kid-friendly house rentals

*NEW* fire pit, by Long Pond + Greenland Pond
A beautiful home with the perfect Cape Cod vibe! Sat by the fire-pit in the backyard a couple of nights and it was so peaceful! It’s centrally located on the Cape. I walked a couple mornings in the neighborhood and felt safe, it’s a very quaint neighborhood!

Old Cape Charmer
The Cape Charmer was better than expected. It was suprisingly kid friendly. Our one year old really loved crawling around the soft carpet in the living room. The space was even nicer than the photos and the beds were extremely comfortable. Would book again.

Water Front Pond House - 3 acre Cape Cod Sanctuary
The house is clean and comfortable, well equipped with kayaks, life vests in different sizes, and table tennis. We enjoyed kayaking on the pond and fishing from the dock in the garden. The location is very convenient: it's near Brewster flats, seashores, Chatham Pier fish market, and Snow Owl cafe. We visited some antique shops in Brewser and played mini golf in Yarmouth. We really enjoyed our stay in Cape Cod.

Relaxing Eco-Friendly Home Next to Long Pond Beach
Very responsive host. Clean house with separate TV room and dining room. Equipped kitchen. Quiet neighborhood with short drives to many amenities. Walking distance to pond. Perfect for a girls weekend away. We added a day mid-trip because we were having such a good time!

Cozy Cape Condo minutes from Brewster beaches
Justin was a great host. From the start, he was awesome with communicating and made sure we felt right at home. The place was clean and exactly what we had hoped for.

4BR/3B | Pond | BikePth | W/D | FireTbl | AC |Deck
Peter was kind, gracious and very responsive. They have a pristine, lovely home in a very peaceful neighborhood and we are grateful for the opportunity! Would love to come back.

Waterfront 4BR Home on Cape Cod
We had a wonderful stay at Jasmine's place. Everything was perfect. Jasmine was there to communicate with at all times. I would recommend this place for others. Thank you Jasmine.

cape cod riverview cottage
First of all, Nancy is a wonderful hostess. She responds almost immediately to inquiries. Now, about the cottage, this is absolutely one of the loveliest cottages I have ever stayed in. Nancy has decorated it in such a manner that it is comfortable, gorgeous, efficient, and I could go on and on. The cottage is actually more lovely than the photos on the website. The home is on the river and the views are lovely. We spent each evening sitting in lounge chairs watching fish jump. There are two bedrooms upstairs and the second floor has its own air conditioning/heat controls. The bathroom is large, and the shower is amazing. Downstairs is a laundry room with washer & dryer, sink and toilet. The first floor has the living room, kitchen and dining area. The first floor has its own ac/heat controls. The kitchen has everything you will ever need. The house is fragrance free and mold free. I definitely would stay here again.
Family-friendly apartment rentals

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Such a lovely place! Peaceful, super clean, and overall excellence! Best Airbnb experience I've had so far!

Peace By The Bay
Bill and Trish were amazing hosts, and they made sure the place was exceptionally clean. They even had fresh flowers for us when we arrived.

Walk to private beach, spacious peaceful apartment
Diana and Greg's place is a wonderful place to stay, brimming with nature, quaint and comfortable living space and wonderful hosts. A nice walk to the beach, enjoyed the birds and frog sounds were the highlights and Orleans allows the entire Cape Cod to be accessible under an hour drive. An awesome weekend adventure and appreciate Diana and Greg opening up their doors! Cheers!

2 BD Suite Mayflower Beach & Dennis Village
Christina’s home was pretty, quiet, comfortable and well stocked. We appreciated that there was coffee, tea, sugar, soap and everything we needed in the kitchen. The location was also superb- very close to several gorgeous beaches plus multiple restaurants and shops. We did not have a chance to use them, but she even had bikes, which would be wonderful in warm weather. This is a great listing. I thoroughly recommend it!

The Knoll
Peg’s home was perfect for our stay in Chatham. It was quiet and peaceful but close enough to Main Street and everywhere we would want to go during our visit.

Cozy Waterfront Apartment, Private Beach Access
My fiancé, dog Bandit, and I stayed here for a few days and it was comfortable & had everything we needed. The private beach was a 10/10. Perfect place to watch the sunrise and there are gray seals constantly swimming by near the shore, so cool!! Make sure you take a look at the ideas and recommendations that Patty left in the blue ring binder. I recommend the Rock Harbor Grill for dinner & Ice Cream Cafe for dessert. Close by to the awesome rail trail for dog walks and only a 50ish minute drive to the tip of the Cape Cod National Seashore. I will say BEWARE of ticks if you’re walking your dog. They are plentiful in Cape Cod, believe it or not. Finally, Patty was a wonderful host. We would definitely choose this Airbnb when visiting Cape Cod again.

Apartment suite|pond access|Firepit|Private Deck
I got this Airbnb for the weekend because I was proposing to my girlfriend in a Hyannis dinner train. This was the only spot that looked private and worthy of an “engagement weekend getaway” vibe as opposed to hotels and other Airbnbs. Meagan even allowed a friend of mine to show up and decorate the apartment with “Just Engaged” signs and fake candles and fake rose petals, which made the bedroom look even more romantic. My now-fiancé could not express enough how much she loved the place. Quiet, safe neighborhood, good eating spots less than 10 mins away in car, great water pressure, everything you could ask for. If we’re going to be knit-picky, the only thing we can complain about was that the A/C did not seem to work. The wall unit was open like if it was working, but no air was coming out of it. I forgot to mention this to Meagan during our stay, as I’m sure she would have rushed to help us. We slept with the windows slightly open and it was just as nice.

Cozy Apartment in Downtown Harwich Port
This is my third time staying at this quaint place! Great location, quiet, and everything you need for a couple!
Family-friendly apartment rentals

Steps to Private Beach in Chatham
Great location for a quiet, peaceful Cape Cod family getaway. Perfect space for group of 4, located on quiet corner of Chatham/cape cod. Very walkable to downtown and lighthouse beach (best beach in cape cod). Julia is a wonderful host, extremely responsive and her local recommendations for visitors were outstanding, especially for first time visitors to CC. Would recommend.

Walk to beach! Chatham Luxury near downtown, CBI!
Kathryn place was just as advertised. Was a lovely unit and easy to explore Chatham in the surrounding areas. Katherine provided clear check in instructions and followed up promptly with any questions we had. I would definitely recommend staying here.

Hidden Hideaway
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.

The 5 minute walk to beach Super Cute Beach Condo
I had a wonderful stay! The space was clean, quiet, and very comfortable. Perfect for a good night’s sleep after spending the day out. I came to Dennis, MA to celebrate a friend’s birthday and used the space primarily for resting, and it was just what I needed. The heat worked well, and the check-in and check-out process was smooth and hassle-free. Overall, I really enjoyed my stay and would definitely return if I’m in the area again.

Golf Course Views and Pools
My wife and I wanted a little end of summer get away and we couldn’t have been happier choosing Alexa’s condo at Ocean Edge! The condo was beautifully decorated, very clean, and everything we could have wanted for our short vacation. Alexa was always very responsive and friendly, we’ll certainly be keeping her in mind for our next cape vacation! Highly recommend for small families and couples!

In-town, Pied-a-Terre. Private, Sunny Urban Oasis
Thank you for the warm welcome, useful information, and a lovely space to stay while visiting the Cape! We would definitely come back!

6 Min to Beach - Pool - Private Balcony - Central
My boyfriend and I stayed in this beautiful and quaint condo for a wedding weekend in Dennis and it couldn’t have been a more perfect place with a more perfect location!We both felt safe and comfortable immediately upon arrival and loved spending time outside on the porch and enjoying walking around the area! We would both recommend this stay to anyone!

A Spectacular. Walk to beach, town and harbor 20
Amazing stay. Didn’t have to get an Uber once, everything was walkable. Brian communicated consistently.
Quick stats about holiday rentals that are kid-friendly in Brewster
Total rentals
110 properties
Nightly prices starting at
₹7,721 before taxes and fees
Total number of reviews
4.6K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Sagamore Beach
- Sandwich Glass Museum
- Owen Park Beach
- Coast Guard Beach
- New Silver Beach
- Onset Beach
- Nickerson State Park
- Oyster Harbors Beach
- Pinehills Golf Club
- Scusset Beach
- Inman Road Beach
- Kalmus Park Beach
- Ridgevale Beach
- Cahoon Hollow Beach
- Peggotty Beach
- Minot Beach
- Grey's Beach
- Grays Beach