Family-friendly vacation rentals in Chatham

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chatham family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A spacious home surrounded by lush greenery is depicted. The yard features a deck with blue chairs and a patio umbrella, along with a variety of flower gardens. Hammocks and outdoor lighting add to the inviting atmosphere of the outdoor space.
Home in Eastham
4.99 out of 5 average rating, 80 reviews

The Penney House Retreat/Hot Tub Gardens, Peace

KathleenRating, 5 stars10 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
The sunroom features a poker table and a foosball table, surrounded by large sliding doors that allow for natural light and fresh air. A ceiling fan is present to enhance airflow. The space is designed for leisure with a clear view of the outdoors.
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 favorite
The exterior of a multi-level home is shown, featuring large windows and a wrap-around deck. A screened porch is visible on the lower level, while manicured grass surrounds the structure. The sky is clear, providing ample natural light to the setting.
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 favorite
The exterior of the house is surrounded by well-maintained greenery and tall, lush trees. A welcoming front entrance is framed by neatly trimmed hedges, leading to a slate pathway and steps. Large windows allow natural light to brighten the façade.
Home in Centerville, Barnstable
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 favorite
The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.
Home in Oak Bluffs
4.93 out of 5 average rating, 199 reviews

Spectacular beach & pool combo; beautiful sunsets!

RobynRating, 5 stars1 week 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 favorite
A spacious living area features a plush, white sectional sofa positioned around a decorative rug. Natural light enters through large windows adorned with arches. A wooden table holds a small vase with flowers, while an inviting fireplace enhances the cozy ambiance.
Apartment in Oak Bluffs
4.93 out of 5 average rating, 137 reviews

Victorian Oasis: Driveway, hot tub, grill & more

SaraRating, 5 stars4 days 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 favorite
The open living area features a light-colored sofa paired with two armchairs, centered around a wooden coffee table. Bright natural light floods the space through large windows and sliding doors, which provide views of the outdoor patio and garden.
Home in Edgartown
4.98 out of 5 average rating, 65 reviews

On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach

HannahRating, 5 stars1 month ago
We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!
Top guest favorite
A spacious driveway leads up to a custom-built house surrounded by trees. A large circular garden bed with dark mulch is accentuated by a flagpole displaying the American flag. Multiple buildings are visible, including a garage and a shed.
Home in Edgartown
4.99 out of 5 average rating, 78 reviews

Edgartown Beauty: The Perfect Retreat, Dogs OK

JaredRating, 5 stars4 months ago
Beautiful home! David gave perfect instructions for everything about the house and was very responsive. We all had a fantastic weekend, and will definitely be booking again! Thank you David!

Family- and pet-friendly home rentals

Guest favorite
A cozy living area is presented with light-colored walls and wooden floors. Comfortable seating includes two upholstered chairs and a sofa with a neutral cover. A coffee table sits in front, and the open kitchen is visible in the background, enhancing the space's inviting nature.
Home in Truro
4.89 out of 5 average rating, 221 reviews

Cape Cod Getaway 2 Bedroom Cozy Home

PaulaRating, 5 stars6 days ago
This place was spotless. It was bright and neat. Nice decorative touches. Nicole was clear on all instructions and was very communicative. The area is very quiet. It’s 15 from p town and downtown Welfleet. If felt like a home and not a rental
Top guest favorite
A cozy living area is equipped with comfortable seating, including a gray couch and armchair. A nautical-themed rug anchors the space, while a wall clock and decorative items add character. A fireplace against the light-colored wall enhances the welcoming atmosphere, with a view of the kitchen beyond.
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.
Superhost
A bright living area features a high cathedral ceiling with wooden beams. Two comfortable sofas are arranged around a coffee table, and a wood-burning stove is positioned beside large glass doors that open to the outdoor deck. Natural light streams in from the windows.
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 favorite
The cottage exterior features a shingle facade with flower boxes adorned with colorful blooms. Two large windows provide natural light, while a wooden step leads to the entrance. The surrounding yard is well-kept, with green grass and vibrant hydrangeas adding to the inviting atmosphere.
Cottage in West Yarmouth
4.84 out of 5 average rating, 240 reviews

Charming Cottage near Beach and Ferry.

SaraRating, 5 stars3 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 favorite
A charming pond-side house is nestled among well-manicured gardens, featuring colorful blooming azaleas. Large windows offer views of the surrounding landscape. A gravel driveway leads up to the property, with the water visible in the background under a clear, blue sky.
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.
Superhost
A serene beach scene is captured at sunset, displaying gentle waves lapping at the shore. The sky transitions through warm colors of orange, pink, and soft purple, while the calm water reflects these hues, enhancing the peaceful ambiance of the coastline.
Guesthouse in Plymouth
4.8 out of 5 average rating, 215 reviews

A peaceful retreat on Cape Cod Bay

ZackRating, 5 stars1 month ago
Awesome little cottage for a week! We spent a whole week at this place and loved it! Tanya was so kind with instructions how to get in and was available for if we needed anything at all. The location is spectacular steps from the private beach, near some great restaurants and stores. The space is small but really all the essentials you need to have a relaxing quiet stay. Would definitely stay again and it’s the perfect place for a getaway.
Guest favorite
A dining area with a round table is surrounded by four woven chairs, providing a welcoming space for shared meals. A chandelier hangs above, and floral wallpaper adorns the walls. A cozy living area with bookshelves and a sofa is visible in the background, enhancing the home’s charm.
Home in South Chatham
4.76 out of 5 average rating, 181 reviews

Historic 1799 Retreat, walk to beach and dining

PritiRating, 5 stars1 week ago
We stayed at this historic home in South Chatham for a week during the first week of June. Great library, cozy interiors and a beautiful yard at the back, this cabin is comfortable and complete with a full kitchen and laundry amenities for a longer stay. The backyard was a peaceful retreat with birds, bunnies and turkeys visiting, where our toddler daughter spent hours playing. While here, we spent a week exploring Cape Cod National Seashore and the lighthouses in and around the Cape. Historic Chatham Lighthouse and Lighthouse beach are within few minutes drive from this home and provide opportunities for quiet wildlife viewing. Also situated close to ferries that travel to Martha's Vineyard and Nantucket. Highly recommend staying at this cabin. We will visit again.
Top guest favorite
A well-maintained garden is visible, featuring lush green grass and vibrant flowerbeds. Blue hydrangeas and a variety of leafy plants are arranged in circular beds, surrounded by mulch. A bird feeder stands in the center, with trees providing a natural backdrop.
Apartment in Barnstable
4.99 out of 5 average rating, 270 reviews

Your dog will love it here and you will too.

ToriRating, 5 stars2 weeks ago
We had a wonderful stay at Pam’s charming Barnstable apartment! The space was clean, cozy, and had everything we needed (& more!) for a relaxing visit. Pam was welcoming, helpful, & kind to us & our two huskies (one of which can be awfully chatty) :) It's not always easy to find pet-friendly places, and we’re so grateful for her kindness & hospitality. The pups had a blast exploring the fenced in yard & doggy door. The location was quiet and peaceful, yet still conveniently located to beaches, shops, & restaurants a short drive away. It was the perfect home base for exploring the Cape, and a great spot to unwind at the end of the day. We felt right at home & would absolutely stay here again. Highly recommend — especially for fellow dog lovers!

Family-friendly home rentals with a pool

Guest favorite
Condo in Provincetown
4.97 out of 5 average rating, 216 reviews

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

OctaviaRating, 5 stars1 week 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
The studio features a floral-patterned bedspread atop a spacious bed. A kitchenette with appliances is visible in the background, along with a dining area that includes a table and four chairs. A comfortable sofa is positioned nearby, with a television mounted on a wooden dresser.
Condo in Hyannis

Courtyard Resort Condo Hyannis

NilsRating, 5 stars96 months ago
Great place. Very central to Main Street. Quiet, plenty of space, good parking, easy communication and check-in. We will come again!
Guest favorite
A clear, inviting pool is seen with a smooth surface reflecting the sky above. Lounge chairs are arranged neatly around the pool area, with several placed alongside a white picket fence. The tranquil setting is enhanced by distant views of the horizon.
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

Relax....You're on Island Time......

JocelynRating, 5 stars10 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Top guest favorite
A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.
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!!
Top guest favorite
A clear blue pool is surrounded by a deck featuring multiple loungers and shaded seating areas. Lush greenery is visible in the background, providing a private and serene environment. A gentle shimmer is seen on the water's surface, inviting guests to enjoy the space.
Apartment in Hyannis Port
4.84 out of 5 average rating, 51 reviews

1 bedroom apartment located 5 minute walk to beach

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
Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.92 out of 5 average rating, 48 reviews

Private 3bdrm Condo Tashmoo Woods

MaryRating, 5 stars9 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!
Guest favorite
A comfortable living area features a dark sectional sofa and a light wood coffee table. A large flat-screen TV is mounted on the wall. Bright natural light filters through sliding glass doors, revealing views of the ocean and outdoor deck. Light furnishings enhance the airy feel.
Condo in Provincetown
4.93 out of 5 average rating, 102 reviews

Modern, clean waterviews

LexiRating, 5 stars1 month 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
The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
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.

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

  • Total rentals

    490 properties

  • Nightly prices starting at

    G$18,838 GYD before taxes and fees

  • Total number of reviews

    12K reviews

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

Destinations to explore