Family-friendly vacation rentals in Chatham

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chatham

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Chatham

4.9 out of 5 average rating, 115 reviews

Cute cottage walking distance to Ridgevale Beach

Retreat to this very quiet and peaceful residential shore neighbored on a dead end street. If LOCATION is what you're looking for, look no further! This year round cottage will serve as a comfortable and relaxing home away from home for your vacation, with walking rights to Ridgevale Beach about 300 yards from the front door. Provided in your home away from home vacation house are linens, towels, fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, & 4 season porch to relax on.

Oct 27 – Nov 3

G$47,480 GYD per night

Guest favorite

Place to stay in Wellfleet

4.97 out of 5 average rating, 168 reviews

WoodsideTiny House near Wellfleet Bay

Our tiny house tucked under trees is the perfect getaway. Walk past our orchard to get to your "Romantic Hideaway". This special rental has a private, sunny deck, a Nordic shower, stained glass windows and a library of books/vinyls. Set back from a quiet road on our property, this little gem is walking distance to Wellfleet's center, harbor & many restaurants, & just minutes drive from National Seashore beaches & ponds. A fun time in bustling Provincetown awaits you only 15 miles down the road!

Sep 18 – 25

G$35,691 GYD per night

Guest favorite

Home in Harwich

4.88 out of 5 average rating, 113 reviews

Cape Cod Retreat close to bike path

A sweet light filled 4 season single family home with three-bedroom, two full bathrooms, central ac and a huge outdoor shower in Harwich, MA. This home is set back from the road with foliage providing privacy and an expansive back yard. The main living area boasts gorgeous, wide pine floors and an open concept floor plan with a bright fully equipped kitchen and vaulted ceilings. With a huge backyard with plenty of privacy, it is perfect for relaxing with friends and family. Close to bike path.

Jan 22 – 29

G$73,827 GYD per night

Guest favorite

Condo in Dennis

4.99 out of 5 average rating, 172 reviews

Studio, 300 yards to Glendon Beach; Seahorse#2

Newly renovated, 250 sq ft studio at Near Beach Rentals. 300 yards to Glendon Beach means you can head to the beach in the morning and you're close enough to walk back for lunch. Fully furnished studio includes a queen bed and a fold down couch, kitchen with stove, fridge, coffee maker and microwave, air conditioning, 40" smart TV, newly renovated bathroom, Wifi, and access to the shared courtyard with grills and furniture. **(6) total units makes NBR a great place for larger gatherings!!!

Sep 12 – 19

G$28,585 GYD per night

Guest favorite

Cottage in Dennis

4.94 out of 5 average rating, 217 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

Nov 9 – 16

G$34,882 GYD per night

Guest favorite

Home in Chatham

4.95 out of 5 average rating, 241 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Mar 26 – Apr 2

G$90,070 GYD per night

Guest favorite

Apartment in Harwich

4.9 out of 5 average rating, 263 reviews

The Secret Garden

Bright and spacious garden level apartment. One floor living, one queen bedroom, private bath, living room with queen pullout and limited kitchenette. Tranquil setting. Your own entrance and patio. A mile to Pleasant Bay, Eastward Ho golf course and Wequassett Inn, shopping, restaurants and beach. Your own private patio. Walk the labyrinth, gardens and fairy gardens. Take an outdoor shower. Cable TV in bedroom as well as living room plus wifi. The hosts live on the top floor of the home.

Apr 14 – 21

G$41,666 GYD per night

Guest favorite

Apartment in Chatham

4.97 out of 5 average rating, 235 reviews

The Knoll

A quiet home nestled next to conservation land. You will be greeted by a big friendly white dog, hear the gentle water fall of a small pond. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

Oct 6 – 13

G$42,087 GYD per night

Guest favorite

Apartment in Barnstable

4.99 out of 5 average rating, 231 reviews

Your dog will love it here and you will too.

If you love to travel with your dog (dogs), like I do, then this is the perfect place for you and your dog. We have a large fenced in yard for your dog to play in and for you to relax in with your dog. We have a one bedroom apartment with a full kitchen, bath, living room and dining area When you book would you PLEASE let me know whether or not you will be traveling with a dog and if you are what breed of dog will you be bringing. Thanks!

Apr 4 – 11

G$31,876 GYD per night

Guest favorite

Guesthouse in Brewster

4.94 out of 5 average rating, 213 reviews

Charming Antique Cape Cod Cottage

Our cottage is situated in a lovely, landscaped yard with a private deck and back yard for our guests. We have a self check in that allows for privacy. While there is a feeling of privacy, you are close to stores and other conveniences. There are many walking trails nearby and beaches for outdoor activities. Perfect location for getting away or seeking adventure.

Dec 13 – 20

G$31,715 GYD per night

Guest favorite

Cottage in Chatham

4.9 out of 5 average rating, 128 reviews

Forbes, a South Chatham cottage

This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only !

Nov 11 – 18

G$32,563 GYD per night

Guest favorite

Apartment in South Orleans

4.92 out of 5 average rating, 123 reviews

Walk to private beach, spacious peaceful apartment

Fully separate, pristine 1-BR apartment a short walk from Little Pleasant Bay, in our secluded home on wooded lane, looking out on a small pond. Private entrance and stairs to airy, light-filled, tastefully furnished rooms, with full kitchen and private laundry room. Near Orleans and Chatham.

Feb 25 – Mar 4

G$38,992 GYD per night