Family-friendly holiday rentals in Brewster

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Brewster family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Chatham
4.95 out of 5 average rating, 279 reviews

Slate House - a modern waterfront getaway

ChristyRating, 5 stars3 weeks ago
We enjoyed our stay—it was a quick 5-minute car ride to Main Street. We also enjoyed watching wildlife in the river! I wish we had brought our binoculars!
Guest favourite
Home in Eastham
4.99 out of 5 average rating, 80 reviews

The Penney House Retreat/Hot Tub Gardens, Peace

KathleenRating, 5 stars9 months ago
The Penny's House is close to all the beaches, great restaurants and the bike path is accessible via the back of the property which we loved. Her house is beautiful and the kitchen was fully stocked with all cookware you needed to make family dinners together. My family was very comfortable with out stay here! Thanks, Kathleen,Jack and family
Superhost
Home in South Chatham
4.85 out of 5 average rating, 59 reviews

Perfect for Group w/ Kids & Dogs w/ Hot Tub

KevinRating, 5 stars1 month ago
Stayed for a weekend with a few friends right before the Cape busy season and had a great time. Check-in was extremely easy, all instructions and rules were clear and reasonable, and check-out was very convenient and straight forward. The house matched all the pictures and was exactly as described, and everything was clean and well stocked. In the future I’ll look to stay at a Del Mar managed location again!
Superhost
Home in West Dennis
4.79 out of 5 average rating, 171 reviews

Walk2Beach, HotTub, FirePit, PetsOk

NatalieRating, 5 stars1 month ago
Great stay! Place is in a quiet residential area, yet centrally located and easy to get places. Nice yard and hot tub was a plus (clean and good temp). We didn’t have a chance to use the fire pit, but outdoor furniture and sitting area was nice with space for everyone. House was very clean, beds comfortable. Host was very responsive. Would definitely stay again.
Guest favourite
Home in Dennis
4.92 out of 5 average rating, 50 reviews

Cape Cod Lakefront Home

JustinRating, 5 stars9 months ago
Nice private house with lots of bedrooms, a pool and nice grounds. House was very clean. We had a great time with our family. Can walk to a few places in town, but need to get into the car for most. The Dennis beaches were great and just a short drive away. Would recommend this place for families. The house has access to Scargo Lake, which is nice, but it is a bit of a hike down a good-sized hill. Host was nice and responsive to questions.
Top guest favourite
Home in Centerville, Barnstable
4.97 out of 5 average rating, 155 reviews

Luxury House 0.25 mi from Craigville Beach

AngieRating, 5 stars3 weeks 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!
Guest favourite
Flat in Oak Bluffs
4.93 out of 5 average rating, 136 reviews

Victorian Oasis: Driveway, hot tub, grill & more

MarleyRating, 5 stars1 week ago
It was a beautiful and peaceful place to land after our wedding! We are grateful for the time and would love to come back some day. Sharon, Deb and Rhianna are the most wonderful hosts, very helpful and kind. We will always have lovely memories from here!!
Guest favourite
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars10 months ago
We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

Family- and pet-friendly home rentals

Superhost
Cottage in Sandwich
4.85 out of 5 average rating, 399 reviews

Oceanfront Cottage w/Private Beach ~ Lil’ Sea Sass

KimberlyRating, 5 stars3 weeks ago
Our family celebrated my daughter’s BSU graduation here. We had a lovely time. The house was as described however, a few things stood out, dirty towels left behind from prior guest at the outdoor shower and walls were scuffed, but overall everything was very clean. Beach is very rocky so water shoes and sneakers is suggested. Views are spectacular and the deck is such a great place to relax or have some fun. Beds are also very comfy and the beach fire pit was a hit! Would recommend for sure. Thanks Susan.
Top guest favourite
Home in Dennis Port
4.98 out of 5 average rating, 268 reviews

Shirley's Place - Pet Friendly Sleeps Six!

MeghanRating, 5 stars7 months ago
We loved our weekend at Karen's place! The house was cozy and clean, and had everything we needed for a comfortable stay (including treats for our pup)! The yard and deck were nice and private, and the house was conveniently located to many restaurants, shops, and not far from the water. Karen made us feel right at home!
Guest favourite
Home in Truro
4.89 out of 5 average rating, 218 reviews

Cape Cod Getaway 2 Bedroom Cozy Home

DonaldRating, 5 stars1 week ago
We had a wonderful time at this place. The house was comfortable and spacious, the kitchen was well-stocked and easy to cook in, and we loved walking around the area. The road away from the highway was a quiet, peaceful place to walk, and we had nice runs down the north and south Pamet Roads. It was perfect for our family of four.
Superhost
Home in Wellfleet
4.85 out of 5 average rating, 105 reviews

A Cape Escape with Water Views from Every Room

JonathanRating, 5 stars5 months ago
We stayed at Rob's place for a few days for New Year's Eve and it was great. The house was very comfortable for a few couples to hang out, cook some meals and enjoy the beautiful views. At low tide you can walk from the house down to the marsh and follow some rough trails or walk a little further to Lt. Island for some sandy beach. The wood stove made it great winter haven, to sit by the fire and enjoy the views of the tides rolling in and out. The architecture of the house is also interesting and reminiscent of other Wellfleet modernist homes.
Top guest favourite
Cottage in Dennis Port
4.94 out of 5 average rating, 212 reviews

Walk to beach - firepit - fireplace

OlitaRating, 5 stars2 months ago
Sue's place was perfect for our mother-daughter weekend. Sue provided a comprehensive list of restaurants in the area, but we prepared all of our meals in the kitchen, which was well-appointed, very much appreciated. We enjoyed daily walks to the beach. Though it was off-season and overcast, inside it was perfectly cozy. The fireplace was great to return to. Sue was quick to return texts, and very welcoming. The snack basket was well received! Would highly recommend.
Top guest favourite
Cottage in West Yarmouth
4.84 out of 5 average rating, 240 reviews

Charming Cottage near Beach and Ferry.

SaraRating, 5 stars2 weeks ago
We traveled to the cape for a youth soccer tournament and wanted to find a place with room for our family and dog. Daniel's cottage was perfect for our family of 4 - a nice cozy cottage with beach access, all the comforts of home, and a great location. Daniel was a great host - proactive friendly location and a clean house with everything we needed.
Guest favourite
Loft in Wellfleet
4.94 out of 5 average rating, 321 reviews

Comfortable Studio Apartment

MonicaRating, 5 stars2 months ago
This place had everything you might need for a stay on Cape. Cute, clean, comfortable, close to bakery/restaurant and beach. Easy parking, great communication and supremely quiet in the off season. Bed was comfortable and mini-split kept the space perfectly cozy. Plenty of storage space. Had hot showers with good water pressure. This was a little gem with a nod towards history of the early 1900s when it was made. Perfect for a solo trip or a couple with a baby. Book it!
Guest favourite
Home in Chatham
4.96 out of 5 average rating, 210 reviews

Studio cottage in Chatham Ma.

JeanetteRating, 5 stars1 month ago
Absolutely adorable! Would stay here again! Be sure to read the details when you get there (my fault I learned you can’t take 2 hot showers back to back…they do tell you that but I missed it). Great location. Perfect crash pad for a weekend as wedding guests!

Family-friendly home rentals with a pool

Superhost
Apartment in Provincetown
4.97 out of 5 average rating, 216 reviews

P-Town Beach Beauty on the Bay. Water View!

OctaviaRating, 5 stars2 days ago
Rob was a great host ! He responded within a timely manner and the place was very clean and felt just like home. I would suggest bringing board games and such for the rainy days. For the folks who enjoy cooking the kitchen was fully stocked with everything you need. I would also recommend renting bikes or taking an Uber if you don't like walking. The walk to town was about 25 minutes. Overall great stay would love you stay her again it gives you the peace and quiet while also being close enough to everything and a beautiful view of the ocean.
Superhost
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars7 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Superhost
Flat in Hyannis Port
4.84 out of 5 average rating, 51 reviews

1 bdrm 4ppl apartment,stairs,pool,no meals,deck

MichaelRating, 5 stars10 months ago
We stayed in the tree house suite. It had a lovely deck surrounded by trees and a great view of the sky. Craig and Ginny are as friendly a couple you will ever meet--always quick to answer questions and offer some great suggestions, Craig even offered to drop us off at a few places. They were so kind they felt like old friends. The beach is beautiful and a five minute walk away--which is great because they charge 25 bucks to park. So do the easy walk, and Ginny will provide chairs, towels, and umbrellas. Hyannis itself is a great place to walk around with lots of shops and great restaurants. We also took a ferry to Nantucket which was delightful, as well. I would visit them again without question. Go. You won't be disappointed. Michael and Rebecca
Superhost
Apartment in Tisbury
4.92 out of 5 average rating, 48 reviews

Private 3bdrm Condo Tashmoo Woods

MaryRating, 5 stars8 months ago
Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!
Superhost
Townhouse in Mashpee
5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars84 months ago
The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.
Superhost
Apartment in Provincetown
4.93 out of 5 average rating, 102 reviews

Modern, clean waterviews

LexiRating, 5 stars3 weeks ago
We had a wonderful stay at Garrett’s place. The apartment location can’t be beat, right on the water and walking distance to town but also nice and peaceful. Our family enjoyed the balcony and the comfy living room and kitchen. Would recommend!
Superhost
Apartment 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.
Townhouse in Brewster
4.95 out of 5 average rating, 39 reviews

Cape Cod's Best! Ocean Edge 2BR Billington "A"!

FernandoRating, 5 stars11 months ago
Jonathan was exceptionally responsive to any communication. He reached out to the desk at the clubhouse so they were prepared for us when we went to purchase our pool passes which made the transaction that much faster. Our kids had a blast at the pool and enjoyed their stay overall. Was super easy to get to my conference - will book again next year!!

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

  • Total rentals

    360 properties

  • Nightly prices starting at

    ₹6,851 before taxes and fees

  • Total number of reviews

    8.9K reviews

  • Pet-friendly rentals

    140 properties allow pets

  • Rentals with a pool

    50 properties have a pool

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

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