Kid-friendly holiday rentals in Chatham

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Chatham

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

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Guest favourite

Home in Chatham

4.96 out of 5 average rating, 105 reviews

Amazing Family Friendly in-town - Chatham 5bedroom

Located on a quiet street steps from Main Street in the heart of downtown Chatham, this property has more charm than you can imagine! A brand-new luxury kitchen, new baths, and central Air Conditioning! The side yard is quiet and offers a calming place to unwind. The house is an easy walk to the beaches, shopping, and restaurants. Movie theater and ice cream place is just a couple steps away. It doesn't get any closer and easier. Leave the car at the house and walk everywhere! Large dining table for 10 and all the linens provided too. Perfect place for your family vacation! You have 2 King beds, 6 Twins and a Futon. House has parking for three cars but no car is necessary you walk to everything. Four bedrooms are upstairs along with a nice reading nook that looks out above the front door. Downstairs is two generous size living rooms, both with flat screen TV's. Nice kitchen with Island and bar as well as a dining table for ten that sits in a lovely sun porch. Walk directly onto your own yard and enjoy a barbecue after walking home from the beach.. The house is all yours. I spend lots of time in Chatham during July, but may not be on the Cape much during August. Either way I'm always a phone call away. Main Street offers easy proximity to beaches and award-winning restaurants and shopping. The location, a few steps away from downtown Chatham, is unbeatable. It's a quiet and peaceful street, yet close to the downtown hustle and bustle. The side yard is peaceful and quiet. You'll love all the space this five bedroom home has to offer. The house has two designated parking spaces in the driveway. If you have compact cars, you might be able to squeeze one more in too. A third parking space is just alongside the fence, but keep it close to the curb so that the neighbors have enough space to pull out of their driveway. One of the things we really enjoy about our home is our setting within a neighborhood, where the neighbors are nearby. Please be considerate of your noise outside. At night, we make sure that things are quiet outside by 10:00 pm, and ask that you do the same. Also, please turn off all exterior house lights at the end of the night.

22–29 Apr

$1,518 SGD per night

Guest favourite

Guest suite in Chatham

4.94 out of 5 average rating, 144 reviews

The Captain Kimball House of Christmas Joy

Experience Cape Cod while staying in this historic 1735 Salt Box built by Captain Kimball Eldredge. You will have a private entrance and the entire second floor dwelling to yourself. Conveniently located on 28 with just a short walk to the beach, this recently renovated home showcases colonial craftsmanship with the original wood floors and fireplaces. Two restaurants a stones throw away, the Cape Cod Rail Trail down the street and only a five minute drive to downtown Chatham or Harwich Port.

10–17 Sep

$280 SGD per night

Guest favourite

Apartment in Chatham

4.96 out of 5 average rating, 279 reviews

In-town, Pied-a-Terre. Private, Sunny Comfy Home.

Bright, Sunny, fabulous in-town location. CLEAN, SAFE & PRIVATE hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, business trips, overflow guests. Comfortably furnished, thoughtfully outfitted. Quality linens, duvet etc. Walk to restaurants, cafe/bakery, groceries, shops, ballpark, Oyster Pond Beach, CBI, tennis courts, bike path, bike rental, etc etc. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

6–13 Dec

$226 SGD per night

Guest favourite

Guest suite in Chatham

4.99 out of 5 average rating, 203 reviews

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table, private access to the fresh water pond, outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

4–11 Sep

$346 SGD per night

Guest favourite

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.

6–13 Dec

$572 SGD per night

Guest favourite

Cottage in Chatham

4.96 out of 5 average rating, 216 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property.

19–26 Oct

$313 SGD per night

Guest favourite

Guest suite in Harwich

4.99 out of 5 average rating, 545 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Nine year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

5–12 Sep

$231 SGD per night

Superhost

Home in Chatham

4.82 out of 5 average rating, 135 reviews

Delightful Chatham Cottage, Cheerful and Clean

AirBnB Superhost, local owner has 20 years of online vacation rental experience with this property. Recently refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at a very affordable price. Enjoy a relaxing stay while being close to everything in town.

8–15 Jun

$246 SGD per night

Guest favourite

Guest suite in Brewster

4.95 out of 5 average rating, 153 reviews

Cozy and Secluded Apartment/Seasonal garden view

Walk across your private patio through sliding glass doors to your private garden retreat in this spacious studio. A large bathroom is just off the kitchen. This brand new apartment is designed for your perfect vacation or retreat from city life. If you are working from home - try working from Cape Cod! A desk awaits you - leave your computer set up and ready! Not the best apartment for disabilities - the entrance is in the back and there is a step up into the shower.

26 Feb – 5 Mar

$130 SGD per night

Guest favourite

Guest suite in Harwich

4.94 out of 5 average rating, 227 reviews

Cape Hideaway

Private suite on the first floor guests have exclusive use of the entire place. The second floor is my residence. The suite has a bedroom with queen temperpedic mattress, living room with queen sleep sofa, small kitchenette and bath. The kitchen is equipped with a small refrigerator, microwave, coffee maker, kettle, single burner cooktop and crockpot. Guests have access to the upper deck (shared space) which has a patio set and gas grill.

26 Dec – 2 Jan

$146 SGD per night

Guest favourite

Guest suite in Orleans

4.92 out of 5 average rating, 143 reviews

Charming Old Cape Cod

Relax and enjoy spending time at Snowtop on the Town Cove, many activities including sailing, paddle boarding, water skiing and spectacular sunsets! A short walk to swim, sit on the sand or take a beach walk. The offered space has a private entrance with bath, bedroom with a king size bed, a sunny living room with dining table over looking the water where you could choose to dine in, have coffee in the morning or play a game.

18–25 Sep

$187 SGD per night

Guest favourite

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 !

5–12 Nov

$211 SGD per night