Family-friendly holiday rentals in Chappaquiddick

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Lovely 2 BR Oak Bluffs Apartment

*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!

KitchenFamilyNearby

4.95 out of 5 average rating, 441 reviews

The exterior of a cape style home is presented, featuring a dark wood shingle facade and multiple gabled rooflines. A white front door is flanked by evergreen shrubs, while a stone path leads to the entrance. Lush green grass surrounds the property, complemented by a wooden fence.

4.92 out of 5 average rating, 106 reviews

Walk to EDG Wharf - Outdoor Shower, AC, and Grill

Just a short walk to Edgartown's shops & restaurants, this cape style home features open concept living, stainless steel appliances, bamboo floors, oversize 2 car garage, washer/dryer and outdoor shower! The master suite includes a sitting area, walk in closet & attached bath with walk-in shower, soaking tub & double vanity. Additional 3 BRs include queen/twin beds & 2 full baths. Kitchen sliders lead to outdoor brick patio with BBQ and dining area. Outdoors games and four bikes included.

FamilyIndoor spacesAccess

5.0 out of 5 average rating, 128 reviews

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Apartment in Edgartown

Perfect for couples, 10 min walk to Edg, big patio

* Private garden patio: string lights create chill evenings around the propane fire pit. Table & chairs, propane grill, & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC

FamilyKitchenLayout

4.9 out of 5 average rating, 155 reviews

A bright living space is visible, with sheer white curtains framing sliding glass doors that open to a private porch. A table with six chairs is seen under a vibrant pink umbrella, providing outdoor seating options for guests.

Cottage in Oak Bluffs

East Chop Cottage - walk to lighthouse & beach!

This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

FamilyKitchenCheck-in

4.93 out of 5 average rating, 113 reviews

A spacious two-story home is set against a backdrop of lush greenery. The exterior features a covered front porch with seating and a well-maintained lawn, complemented by colorful flower beds along the walkway. Large windows invite natural light into the inviting space.

Home in Oak Bluffs

Vineyard Social-Spacious 5BR Home in Oak Bluffs

Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fantastic outdoor spaces, including a large front Farmers Porch and an oversized Patio with a gas grill. Enjoy all the desired amenities, including an outdoor shower, an open kitchen layout, and a 75" Smart TV. Both walkable and bikeable to Oak Bluffs Center and Harbor you can easily explore the town's lively shops, restaurants, and local attractions.

KitchenIndoor spacesAccess

5.0 out of 5 average rating, 171 reviews

A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.

Home in Falmouth

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

KitchenIndoor spacesAir conditioning

A charming Cape-style house features a welcoming front porch with decorative railings and two red doors. Lush greenery and colorful flower beds surround the home, while a pebble driveway leads to the entrance. The exterior is complemented by a clear blue sky.

4.94 out of 5 average rating, 109 reviews

The Seashell Cove - Martha's Vineyard

Nestled in the exclusive Katama neighborhood of Edgartown, this sunny Cape retreat is perfect for families or friends. Just two miles from South Beach, it offers cozy interiors, high-speed Wi-Fi, and smart TVs. Outdoors, enjoy a farmer's porch, deck with a direct gas-line grill, and spacious yards. Close to downtown Edgartown, bike paths, and attractions like the Chappaquiddick ferry, this property is ideal for both summer adventures and peaceful off-season stays.

Indoor spacesFamilyAccuracy

4.93 out of 5 average rating, 326 reviews

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

FamilyKitchenTV

4.97 out of 5 average rating, 126 reviews

A covered outdoor seating area features a comfortable sectional sofa with neutral cushions and a round coffee table. A dining table with several chairs is positioned nearby, alongside an outdoor kitchen equipped with a grill. Sunlight casts distinct shadows across the space.

Home in East Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay

Our 2,400 square feet family-friendly house located on the East Falmouth Seacoast shores awaits your arrival! It is located steps away from the private lush beach bay. Newly remodeled and furnished with an excellent yard space for grilling, relaxation, and games suitable for all ages! Our house features an outdoor hot tub, outdoor kitchen, grill, koi pond, fire pit, outdoor shower, spacious modern kitchen, and kayak ready for your enjoyment.

FamilyIndoor spacesHospitality

Guest suite in Oak Bluffs

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

KitchenFamilyAccess

4.98 out of 5 average rating, 209 reviews

The entrance of a condo is framed by a well-maintained lawn, with vibrant greenery and colorful flowers surrounding the doorway. The front door, featuring a decorative glass panel, opens to a sunlit pathway lined with stone pavers.

4.98 out of 5 average rating, 194 reviews

Close to Edgartown Village Center!

This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 3 bedrooms and a loft and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

KitchenFamilyAccuracy

A light-filled living room is showcased with a comfortable sofa, side chairs, and a flat-screen TV. A brick fireplace is centered in the room, adorned with a round mirror and decorative items. Natural light filters through the windows, enhancing the inviting space.