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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Superhost

A charming cottage is situated on a gravel driveway, framed by greenery and featuring a flagpole adorned with the American flag. A front porch with steps leads to the entrance, complemented by well-kept landscaping and a peaceful atmosphere.

Home in Chatham

4.89 out of 5 average rating, 131 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.

Superhost

The vintage beach cottage is depicted with a light blue exterior, settled near the edge of a sandy beach. Waves gently crash against the shoreline while a lush green area surrounds the cottage, providing a serene coastal setting. A single vehicle is parked near the entrance.

Cottage in Sandwich

4.86 out of 5 average rating, 401 reviews

Oceanfront Cottage w/Private Beach ~ Lil’ Sea Sass

RARE: DIRECT OCEANFRONT & BEACHFRONT CAPE COD COTTAGE — DOG FRIENDLY — LOCATED ON THE COTTAGE’S VERY OWN PRIVATE BEACH! Lil’ Sea Sass is a 3 BR vintage beach cottage that is nestled in the dunes offering unparalleled ocean views and is located in a very private serene setting. This oasis is near the end of a private road and then down a long drive — with free guaranteed parking for 2+ cars! Amenities include: gas fireplace, fire table, FAST WIFI, central AC & heat, and an outdoor shower.

Guest favorite

The exterior of a recently renovated home is shown, featuring a sloped roof and large windows that provide ample natural light. A deck surrounds the house, complemented by landscaped greenery. The setting is open, with a clear blue sky overhead.

Home in Chatham

4.95 out of 5 average rating, 279 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.

Top guest favorite

A wooden sign is displayed, featuring a welcoming message that reads 'welcome to Cape Cod.' The text is artistically styled, with blue waves and a small sailing boat illustrated underneath.

Guest suite in Brewster

4.97 out of 5 average rating, 373 reviews

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

Top guest favorite

A charming tiny house is nestled among lush greenery, framed by trees and flowering plants. A cozy wooden deck with colorful chairs invites relaxation. Nearby, two lounge chairs sit on a grassy area, creating a peaceful spot to enjoy the natural surroundings.

Place to stay in Wellfleet

4.97 out of 5 average rating, 239 reviews

Romantic Cape Cod Tiny House + Hot Tub

Welcome to the Romantic Hideaway, our magical, secluded tiny house nestled between lush gardens and the woods alongside our property. Just a short drive to ocean beaches and freshwater ponds, and a pleasant walk to the quaint center of Wellfleet. Wake to birdsong and enjoy fresh muffins on your sunny, private deck. Your stay includes access to our Magnolia Spa with hot tub and sauna (June+); massage is available in July at special guest rates. A sweet, quiet escape on the Outer Cape.

Guest favorite

The charming cottage is surrounded by lush greenery and colorful flower beds, providing a serene outdoor setting. The siding features a traditional shingle design, while the deck is adorned with greenery, enhancing the peaceful atmosphere of the garden area.

Cottage in Harwich Port

4.91 out of 5 average rating, 150 reviews

"Coaster" Village Location!

Sweet Cottage just a 1/2 mile to Bank Street Beach and only a block from Main Street. The property has lovely gardens and landscaping making it a wonderful retreat setting. Summer months July, August to Sept 10th are at least 1 week rentals Saturday to Saturday unless a few days are available in between or if there is availability as season approaches. Off season, 2 to 3 night stay minimum, I provide linens, coffee and towels for short term rentals. Easy walk to the village and beaches!

Top guest favorite

A charming wooden cottage features a green door and window frames, set against a landscaped garden. A friendly white dog sits on the grass in front of the cottage, surrounded by stone paths and potted plants, offering a welcoming sight.

Apartment in Chatham

4.97 out of 5 average rating, 264 reviews

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. 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.

Guest favorite

The bedroom features a queen bed with a light-colored comforter, complemented by decorative pillows. Two lamps provide soft lighting beside the bed, and a piece of wall art depicts a boat scene. A window allows natural light, with white blinds partially opened.

Apartment in East Harwich

4.9 out of 5 average rating, 283 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 and Wequassett Inn, shopping, restaurants and beach. 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. Off season discounts.

Guest favorite

A charming two-story structure features dark wooden siding and a welcoming entryway. Surrounding greenery includes tall trees and well-maintained shrubs, providing a serene outdoor setting. A grassy area leads up to the building, emphasized by a clear blue sky overhead.

Home in Brewster

4.92 out of 5 average rating, 266 reviews

Privacy with Cape Cod charm

This lovely, private one bedroom apartment is located above the unused garage on the grounds of our classic half cape house, just a 3 minute walk to our private beach on the bay. It sleeps 2 with a double bed and has a full kitchen and bathroom, along with an outdoor shower, grill, fire pit and picnic table located in private yard. Linens will be provided. Coffee maker and coffee will be waiting for you...

Guest favorite

A cozy cottage exterior is displayed, featuring a light gray shingle facade and white trim around the windows. A screened-in porch is visible, accompanied by blue outdoor chairs. The surrounding area showcases a grassy yard with greenery and trees in the background.

Cottage in Chatham

4.9 out of 5 average rating, 149 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 !

Guest favorite

The exterior of the renovated Chatham home features a white picket fence and a gravel driveway. The house showcases a gabled roof and large windows, surrounded by greenery and trees. The clear blue sky above emphasizes the peaceful neighborhood setting.

Home in Chatham

4.91 out of 5 average rating, 186 reviews

Quaint Downtown Chatham Home

This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

Top guest favorite

A serene outdoor seating area is set by the waterfront, featuring two chairs with teal cushions and a white table. Lush greenery surrounds the area, enhancing the view of the calm waters and trees beyond. Lanterns add a subtle decorative touch to the space.

Home in Yarmouth Port

4.99 out of 5 average rating, 351 reviews

Fabulous Waterfront! 3bdrm/2bth Kayaks & Firepit

**Waterfront on salt water Follins Bay which is the headwaters of the Bass River. Sit and watch the boat activity from the deck or patio. Swim, fish or kayak (2 provided) right from your the backyard on your own private dock. Bright & airy décor with beautiful water views.